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Cas Database

107-95-9

107-95-9

Identification

  • Product Name:beta-Alanine

  • CAS Number: 107-95-9

  • EINECS:203-536-5

  • Molecular Weight:89.0941

  • Molecular Formula: C3H7NO2

  • HS Code:29224920

  • Mol File:107-95-9.mol

Synonyms:β-Aminopropionic acid;omega-Aminopropionic acid;beta-Alanine (6CI,8CI,9CI);Propanoic acid, 3-amino-;Alanine, beta-;beta-aminopropionic acid;3-Aminopropionsaeure;a-Alanine;Alanine (beta-);H-β-Alanine;H-β-Ala-OH;3-amino-;.beta.-Aminopropionic acid;3-Aminopropionic acid;beta-Aminopropionsaeure;2-Carboxyethylamine;3-aminopropanoate;Abufene;3-azaniumylpropanoate;3-Aminopropanoic acid;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:b-Alanine
  • Packaging:500g
  • Price:$ 333
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  • Manufacture/Brand:TRC
  • Product Description:β-Alanine
  • Packaging:50g
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  • Manufacture/Brand:Tocris
  • Product Description:Beta Alanine
  • Packaging:1G
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Beta Alanine >99.0%(T)
  • Packaging:25g
  • Price:$ 17
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Beta Alanine >99.0%(T)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:β-Alanine BioUltra, ≥99.0% (NT)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:β-Alanine 99%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:β-Alanine ≥98%, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:β-Alanine ≥98%, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Beta Alanine United States Pharmacopeia (USP) Reference Standard
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Relevant articles and documentsAll total 124 Articles be found

On the radiochemical formation of amino acids by carboxylation and amination

Dose,Risi

, p. 581 - 587 (1968)

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Mechanism of cysteine-dependent inactivation of aspartate/glutamate/ cysteine sulfinic acid α-decarboxylases

Liu, Pingyang,Torrens-Spence, Michael P.,Ding, Haizhen,Christensen, Bruce M.,Li, Jianyong

, p. 391 - 404 (2013)

Animal aspartate decarboxylase (ADC), glutamate decarboxylase (GDC) and cysteine sulfinic acid decarboxylase (CSADC) catalyze the decarboxylation of aspartate, glutamate and cysteine sulfinic acid to β-alanine, γ-aminobutyric acid and hypotaurine, respectively. Each enzymatic product has been implicated in different physiological functions. These decarboxylases use pyridoxal 5-phosphate (PLP) as cofactor and share high sequence homology. Analysis of the activity of ADC in the presence of different amino determined that beta-alanine production from aspartate was diminished in the presence of cysteine. Comparative analysis established that cysteine also inhibited GDC and CSADC in a concentration-dependent manner. Spectral comparisons of free PLP and cysteine, together with ADC and cysteine, result in comparable spectral shifts. Such spectral shifts indicate that cysteine is able to enter the active site of the enzyme, interact with the PLP-lysine internal aldimine, form a cysteine-PLP aldimine and undergo intramolecular nucleophilic cyclization through its sulfhydryl group, leading to irreversible ADC inactivation. Cysteine is the building block for protein synthesis and a precursor of cysteine sulfinic acid that is the substrate of CSADC and therefore is present in many cells, but the presence of cysteine (at comparable concentrations to their natural substrates) apparently could severely inhibit ADC, CSADC and GDC activity. This raises an essential question as to how animal species prevent these enzymes from cysteine-mediated inactivation. Disorders of cysteine metabolism have been implicated in several neurodegenerative diseases. The results of our study should promote research in terms of mechanism by which animals maintain their cysteine homeostasis and possible relationship of cysteine-mediated GDC and CSADC inhibition in neurodegenerative disease development.

-

Ayres

, p. 440 (1975)

-

Photocatalytic One-Step Syntheses of Cyclic Imino Acids by Aqueous Semiconductor Suspensions

Ohtani, Bunsho,Tsuru, Shigeto,Nishimoto, Sei-ichi,Kagiya, Tsutomu

, p. 5551 - 5553 (1990)

Optically active cyclic imino acids, pipecolinic acid and proline, are readily obtained from α,ω-diamino carboxylic acids and their Nω-substituted derivatives by the photoirradiation of aqueous suspensions of TiO2 or CdS loaded with platinum oxides under Ar at room temperature.

Abiotic Synthesis of Amino Acids by Proton Irradiation of a Mixture of Carbon Monoxide, Nitrogen, and Water

Kobayashi, Kensei,Oshima, Tairo,Yanagawa, Hiroshi

, p. 1527 - 1530 (1989)

We have shown that proton irradiation simulating the action of cosmic rays and solar flare particles formed proteinous and non-proteinous amino acids such as glycine, alanine, aspartic acid and β-alanine from a mixture of carbon monoxide, carbon dioxide, nitrogen and water.The yield of amino acids per unit energy was the highest obtained among various prebiotic energy sources used.This result suggests the possibility of the formation of amino acids mildly reduced primitive atmospheres on the earth.

Mass spectrometry assay for studying kinetic properties of dipeptidases: Characterization of human and yeast dipeptidases

Pandya, Vaibhav,Ekka, Mary Krishna,Dutta, Rajesh Kumar,Kumaran

, p. 134 - 142 (2011)

Chemical modifications of substrate peptides are often necessary to monitor the hydrolysis of small bioactive peptides. We developed an electrospray ionization mass spectrometry (ESI-MS) assay for studying substrate distributions in reaction mixtures and determined steady-state kinetic parameters, the Michaelis-Menten constant (Km), and catalytic turnover rate (V max/[E]t) for three metallodipeptidases: two carnosinases (CN1 and CN2) from human and Dug1p from yeast. The turnover rate (V max/[E]t) of CN1 and CN2 determined at pH 8.0 (112.3 and 19.5 s-1, respectively) suggested that CN1 is approximately 6-fold more efficient. The turnover rate of Dug1p for Cys-Gly dipeptide at pH 8.0 was found to be slightly lower (73.8 s-1). In addition, we determined kinetic parameters of CN2 at pH 9.2 and found that the turnover rate was increased by 4-fold with no significant change in the Km. Kinetic parameters obtained by the ESI-MS method are consistent with results of a reverse-phase high-performance liquid chromatography (RP-HPLC)-based assay. Furthermore, we used tandem MS (MS/MS) analyses to characterize carnosine and measured its levels in CHO cell lines in a time-dependent manner. The ESI-MS method developed here obviates the need for substrate modification and provides a less laborious, accurate, and rapid assay for studying kinetic properties of dipeptidases in vitro as well as in vivo.

An application of the Delepine reaction to beta-bromopropionic acid.

WENDLER

, p. 375 - 375 (1949)

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STABILITIES OF WATER-SOLUBLE VITAMINS AND COENZYMES. VI. KINETICS AND MECHANISM OF THE HYDROLYSIS OF CALCIUM D-PANTOTHENATE

Kozlov, E. I.,L'vova, M. Sh.,Ozerinina, T. V.

, p. 153 - 160 (1983)

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Artificial trinuclear metallopeptidase synthesized by cross-linkage of a molecular bowl with a polystyrene derivative

Moon, Sung-Ju,Jeon, Joong Won,Kim, Heesuk,Suh, Myunghyun Paik,Sun, Junghun

, p. 7742 - 7749 (2000)

A novel methodology is reported for construction of active sites of artificial multinuclear metalloenzymes: Transfer of metal-chelating sites confined in a prebuilt cage to a polymeric backbone. Artificial active sites comprising two or three moieties of Cu(II) complex of tris(2-aminoethyl)amine (tren) were prepared by transfer of Cu(II)tren units confined in a molecular bowl (MB) to poly(chloromethylstyrene-co-divinylbenzene) (PCD). By treatment of unreacted chloro groups of the resulting PCD with methoxide and destruction of the MB moieties attached to PCD with acid followed by addition of Cu(II) ion to the exposed tren moieties, catalytic polymers with peptidase activity were obtained. The average number (β) of proximal Cu(II)tren moieties in the active site of the artificial multinuclear metallopeptidase was determined by quantifying the Cu(II) content. Several species of the artificial metallopeptidases with different β contents were prepared and examined for catalytic activity in hydrolysis of various cinnamoyl amide derivatives. The PCD-based catalytic polymers did not hydrolyze a neutral amide but effectively hydrolyzed carboxyl-containing amides (N-cinnamoyl glycine, N-cinnamoyl β-alanine, and N-cinnamoyl γ-amino butyrate). Analysis of the kinetic data revealed that the active sites comprising three Cu(II)tren units were mainly responsible for the catalytic activity. When analyzed in terms of k(cat), the catalytic activity of the PCD-based artificial peptidase was comparable to or better than the catalytic antibody with the highest peptidase activity reported to date. A mechanism is suggested for the effective cooperation among the three metal centers of the active site in hydrolysis of the carboxyl-containing amides.

KINETICS OF THE FORMATION OF PANTOLACTONE FROM PANTOTHENATES AND ITS QUANTITATIVE DETERMINATION

Moiseenok, A. G.,Slyshenkov, V. S.,Lysenkova, A. V.

, p. 88 - 90 (1984)

The conditions of hydrolysis and lactonization of the calcium and sodium salts of pantothenic and pantoic acids have been studied.The selected conditions of hydrolysis (t = 80 deg C, CHCl = 13percent) led to a 100percent yield of β-alanine and pantothenates after 60 min from the beginning of hydrolysis, while the formation of pantolactone was complete in 105 min for the calcium salt and in 75 min for the sodium salt.The hydrolysis and lactonization reactions have been performed under the conditions mentioned, and the GLC of the pantolactone formed has permitted the determination of various concentrations of calcium pantothenate.The results obtained from the GLC analysis of pantolactone indicate the possibility of a quantitative determination of salts of pantothenic and pantoic acids.The sensitivity of this method is 0.2-5 nmole.

A green-by-design bioprocess for l-carnosine production integrating enzymatic synthesis with membrane separation

Yin, Dong-Ya,Pan, Jiang,Zhu, Jie,Liu, You-Yan,Xu, Jian-He

, p. 5971 - 5978 (2019)

l-Carnosine (l-Car, β-alanyl-l-histidine) is a bioactive dipeptide with important physiological functions. Direct coupling of unprotected β-Ala (β-alanine) with l-His (l-histidine) mediated by an enzyme is a promising method for l-Car synthesis. In this study, a new recombinant dipeptidase (SmPepD) from Serratia marcescens with a high synthetic activity toward l-Car was identified by a genome mining approach and successfully expressed in Escherichia coli. Divalent metal ions strongly promoted the synthetic activity of SmPepD, with up to 21.7-fold increase of activity in the presence of 0.1 mM MnCl2. Higher temperature, lower pH and increasing substrate loadings facilitated the l-Car synthesis. Pilot biocatalytic syntheses of l-Car were performed comparatively in batch and continuous modes. In the continuous process, an ultra-filtration membrane reactor with a working volume of 5 L was employed for catalyst retention. The dipeptidase, SmPepD, showed excellent operational stability without a significant decrease in space-time yield after 4 days. The specific yield of l-Car achieved was 105 gCar gcatalyst-1 by the continuous process and 30.1 gCar gcatalyst-1 by the batch process. A nanofiltration membrane was used to isolate the desired product l-Car from the reaction mixture by selectively removing the excess substrates, β-Ala and l-His. As a result, the final l-Car content was effectively enriched from 2.3% to above 95%, which gave l-Car in 99% purity after ethanol precipitation with a total yield of 60.2%. The recovered substrate mixture of β-Ala and l-His can be easily reused, which will enable the economically attractive and environmentally benign production of the dipeptide l-Car.

Fixation of Molecular Nitrogen Using Aliphatic Carboxylic Acid by Nitrogen Arc Plasma. Formation of Amino Acids

Takasaki, Michiaki,Harada, Kaoru

, p. 365 - 368 (1987)

When argon-nitrogen plasma was blown into an aqueous solution containing aliphatic carboxylic acids, formation of several amino acids and amines was identified.

TRANSFORMATIONS OF ACRYLAMIDE AND POLYACRYLAMIDE AT HIGH PRESSURES AND LARGE SHEAR DEFORMATIONS

Chistotina, N. P.,Zharov, A. A.

, p. 944 - 949 (1992)

Radical polymerization and nucleophilic addition of an amide group to the double bond of acrylamide take place parallel in conditions of shear deformation and high pressures (up to 8 GPa). Large shear deformations cause the formation of β-alanine as the result of reactions of hydrolysis of amide groups and peptide bonds. Keywords: pressure, shear deformation, acrylamide, polyacrylamide, radical polymerization, nucleophilic addition, hydrolysis, β-alanine.

Amino Acids in the Hydrolysis Products of the Reaction of Carbon Vapor with Ammonia

Shevlin, Philip B.,McPherson, Daniel W.,Melius, Paul

, p. 7006 - 7007 (1981)

-

The action of hydrogen peroxide on amino acids in presence of iron salts and its bearing on photolysis of amino acids.

KALYANKAR,VAIDYANATHAN,GIRI

, p. 348 - 349 (1955)

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Kinetic and spectroscopic evidence of negative cooperativity in the action of lysine 2,3-aminomutase

Ruzicka, Frank J.,Frey, Perry A.

, p. 16118 - 16124 (2010)

Lysine 2,3-aminomutase (LAM) catalyzes the interconversion of l-lysine and l-β-lysine, a component of a number of antibiotics. The reaction requires the cofactors S-adenosyl-l-methionine (SAM), pyridoxal-5′-phosphate (PLP), and a [4Fe-4S] cluster. LAM is a founding member of the radical SAM superfamily of enzymes. LAM is highly specific for l-lysine and will not accept most other amino acids as substrates. l-Alanine and l-2-aminobutyrate at 0.2 M react as substrates for LAM at, respectively, 5 × 10-6 and 8 × 10-5 times the rate with saturating l-lysine. Saturating ethylamine accelerates the l-alanine reaction 70-fold, and saturating methylamine accelerates the l-2-aminobutyrate reaction 47-fold. The primary amines binding at the active site of LAM with l-alanine or l-2-aminobutyrate simulate l-lysine. The steady-state kinetics of the reaction of l-alanine + ethylamine displays negative cooperativity with respect to l-alanine. The second-order rate constant for production of β-alanine in the reaction of l-alanine and saturating ethylamine is 0.040 M-1 s-1, which is 2 × 10 -5 times the value of kcat/Km for the reaction of l-lysine. When l-lysine is at a concentration 1/16th of Km, the lysyl-free radical intermediate is hardly detectable by EPR; however, the addition of l-alanine at high concentration (0.2 M) enhances free radical formation, and the addition of ethylamine further enhances radical formation. These facts complement the kinetic observations and support negative cooperativity in the reaction of l-alanine as a substrate for LAM. Present results and independent evidence support negative cooperativity in the reaction of l-lysine as well.

Degradation of complexons derived from succinic acid under UV radiation

Smirnova,Khizhnyak,Nikol’skii,Khalyapina, Ya. M.,Pakhomov

, p. 507 - 511 (2017)

The destruction of complexons derived from succinic acid under the action of UV radiation was studied. IR spectroscopy, thin-layer paper chromatography, and complexometric titration were used to determine the destruction products of these complexons. It was found that the complexons decompose under UV irradiation substantially more easily than ethylenediaminetetraacetic acid does, and the products of their decomposition can undergo a biological utilization under natural conditions. The data obtained in the study make it possible to choose, instead of ethylenediaminetetraacetic acid, ligands that will be nearly fully destructible in the light without deteriorating the ecology.

Cleavage of the peptide bond of β-alanyl-L-histidine (carnosine) induced by a CoIII-amine complexes: Reaction, structure and mechanism

Saha, Manas K.,Mukhopadhyay, Uday,Bernal, Ivan

, p. 1466 - 1473 (2004)

Cleavage of the peptide bond occurs when β-alanyl-L-histidine (carnosine) reacts with [Co(tren)Cl2] (tren = tris(2-aminoethyl) amine) to give [Co(tren)(histidine)]2- 1 and [Co(tren)(β- alanine)]2- 2. [Co(tren)(histidine)]2- 1 crystallizes in the enantiomorphic space group P212121 and 2 crystallizes in the P21/c space group. The mechanism of the cleavage reactions were studied in detail for the precursor [Co(tren)Cl2] + and [Co(trien)Cl2]+, which convert into [Co(tren)(OH)2]+/[Co(tren)(OH)(OH2)] 2+ and [Co(trien)(OH)2]+/[Co(trien)(OH)(OH 2)]2+ in water at basic pH [trien = 1,4,7,10- tetraazadecane). At a slightly basic pH, the initial coordination of the substrate (β-alanyl-L-histidine) is by the carboxylate group for the reaction with [Co(tren)Cl2]+. This is followed by a rate-limiting nucleophilic attack of the hydroxide group at the β-alanyl-L-histidine carbonyl group. In a strongly basic reaction medium substrate, binding of the metal was through carboxylate and amine terminals. On the other hand, for the reaction between [cis-β-Co(trien)Cl 2]+ and β-alanyl-L-histidine, the initial coordination of the substrate takes place via an imidazole ring nitrogen, independently, and followed by a nucleophilic attack of the hydroxide group at the β-alanyl-L-histidine carbonyl group. The circular dichroism spectrum for 1 suggests that a very small extent of racemization of the amino acid (L-histidine) takes place during the cleavage reaction between [Co(tren)Cl 2]+ and β-alanyl-L-histidine. Reaction between [cw-β-Co(trien)Cl2]+ and β-alanyl-L-histidine also causes cleavage of the peptide bond, producing a free β-alanyl molecule and a cationic fragment [cis-α-Co(trien)(histidine)]2+ 3 that crystallizes in the optically active space group P212 121. Unlike the previous case an appreciable degree of racemization of the L-histidine takes place during the reaction between [cis-β-Co(trien)Cl2]+ and β-alanyl-L-histidine. Crystals containing L-histidine and D-histidine fragments in the [cis-α-Co(trien)(histidine)]2- moiety were crystallographically documented by mounting a number of randomly selected crystals.

-

Kuettel,McElvain

, p. 2692,2696 (1931)

-

Byalaya et al.

, (1969)

FORMATION OF AMINO ACIDS FROM ALIPHATIC AMINES BY CONTACT GLOW DISCHARGE ELECTROLYSIS

Harada, Kaoru,Nomoto, Masayo M.,Gunji, Hiromi

, p. 769 - 772 (1981)

Oxidation of aliphatic amines in an aqueous solution by contact glow discharge electrolysis resulted in the formation of several amino acids, which was explained by the oxidative action of hydroxyl radical generated by the electric discharge process to the aqueous solution.

THE FORMATION OF α- AND β-ALANINE BY THE INSERTION OF NH(1Δ) RADICALS INTO THE C-H BONDS OF PROPIONIC ACID

Sato, Shin,Kitamura, Takashi,Tsunashima, Shigeru

, p. 687 - 690 (1980)

The formation of α- and β-alanine in the photolysis of hydrogen azide in propionic acid was confirmed by the NMR spectra.The yield ratios, alanine/nitrogen and β/α in alanine were found to be 0.4 and 1.5, respectively, suggesting that NH(1Δ) radicals insert into the C-H bonds of propionic acid.

Formation of amino acids from possible interstellar media by γ-rays and UV irradiation

Takano, Yoshinori,Masuda, Hitomi,Kaneko, Takeo,Kobayashi, Kensei

, p. 986 - 987 (2002)

Formation of amino acids from mixtures of methanol, ammonia and water in various phases by γ-rays and UV irradiation were quantitatively verified. A wide variety of amino acids were detected in every hydrosate of the product. Each G-value (the number of formed molecules per deposit energy of 100eV) was around 10-2 order, which was independent from the phase of the starting materials and kind of the energy.

Nitrilase-catalyzed hydrolysis of 3-aminopropionitrile at high concentration with a tandem reaction strategy for shifting the reaction to β-alanine formation

Han, Chao,Yao, Peiyuan,Yuan, Jing,Duan, Yitao,Feng, Jinhui,Wang, Min,Wu, Qiaqing,Zhu, Dunming

, p. 113 - 118 (2015)

Given the importance of β-alanine, the nitrilase BjNIT3397 from Bradyrhizobium japonicum strain USDA110 was examined toward the hydrolysis of 3-aminopropionitrile. It has been found that nitrilase BjNIT3397 effectively hydrolyzed 3-aminopropionitrile with substrate concentration up to 3 M (210 g/L) at the pH 7.3 and temperature 30°C. With the increase of substrate concentration from 0.6 to 3 M, 3-aminopropanamide was formed and its percentage in the products was increased up to 33%. In order to reduce the formation of 3-aminopropanamide, aspartate ammonia-lyase and fumaric acid were added into the reaction system to consume the byproduct ammonia. As expected, the reaction was shifted toward the formation of β-alanine, resulting in the decrease of 3-aminopropanamide from 33% to 3%. Therefore, a tandem reaction strategy was developed to effectively prevent the formation of 3-aminopropanamide. This might also offer a possibility of producing β-alanine and L-aspartic acid in one process.

-

Giri et al.

, p. 440,441 (1953)

-

FLAME-INDUCED OXIDATION OF ALIPHATIC AMINES IN AN AQUEOUS SOLUTION

Nomoto, Shinya,Takasaki, Michiaki,Sakata, Naoko,Harada, Kaoru

, p. 3357 - 3360 (1983)

When a town gas-, a hydrogen-, and an ethylene-oxigen flame were blown against the surface of aqueous solution of aliphatic amines, the amines were effectively oxidized to afford amino acids.

Production of β-Alanine from Fumaric Acid Using a Dual-Enzyme Cascade

Qian, Yuanyuan,Liu, Jia,Song, Wei,Chen, Xiulai,Luo, Qiuling,Liu, Liming

, p. 4998 - 5005 (2018)

The aim of this study was to develop an environmentally safe and efficient method for β-alanine production using a dual-enzyme cascade route with L-aspartase (AspA) from E. coli and L-aspartate-α-decarboxylase (PanD) from Corynebacterium glutamicum. Poor cooperativity in this system due to the divergent catalysis efficiencies of AspA and PanD led to an imbalance between the two reactions. To address this issue, we employed ribosome binding site regulation and gene duplication to coordinate the expression levels of AspA and PanD. Finally, we achieved β-alanine production of 80.4±1.6 g L?1 with a conversion rate of 95.3±1.6 % in a 5-L bioreactor. The dual-enzyme cascade reported herein represents a promising strategy to meet industrial requirements for large-scale β-alanine production in the future.

Reductive Fixation of Molecular Nitrogen by Glow Discharge against Water

Harada, Kaoru,Igari, Shun-ichiro,Takasaki, Michiaki,Shimoyama, Akira

, p. 1384 - 1385 (1986)

The reductive fixation of molecular nitrogen by glow discharge against water resulted in the formation of ammonia; amino compounds were also formed when the aqueous solution contained carboxylic acids.

The Synthesis of Triterpenic Amides on the Basis of 2,3-seco-1-Cyano- 19β,28-Epoxy-18α-Oleane-3-oic Acid

Tolmacheva,Igosheva,Grishko,Zhukova,Gerasimova

, p. 377 - 382 (2010)

Novel 2,3-seco-triterpenic amides were prepared by the interaction of the chloride of 1-cyano-19β,28-epoxy-18α-oleane-3-oic acid with primary amines and synthetic and biogenic amino acids. A cytotoxic triterpenic conjugate with a residue of the ethyl ester of β-alanine was found among the synthesized nitrogen-containing derivatives. Treatment with this conjugate in a concentration of 100 μM resulted in the 45.5% survival of melanoma cells in the medium. Pleiades Publishing, Ltd., 2010.

-

Takayama,Oeda

, p. 535,537,540 (1934)

-

Poppelsdorf,Lemon

, p. 262 (1961)

A study on the applicability of l-aspartate α-decarboxylase in the biobased production of nitrogen containing chemicals

Koenst, Paul M.,Franssen, Maurice C. R.,Scott, Elinor L.,Sanders, Johan P. M.

, p. 1646 - 1652 (2009)

β-Alanine could serve as an intermediate in the biobased production of nitrogen containing chemicals from l-aspartic acid. Following the biorefinery concept, l-aspartic acid could become widely available from biomass waste streams via the nitrogen storage polypeptide cyanophycin. Since α-decarboxylation of l-aspartic acid is difficult to perform chemically, the applicability of Escherichia colil-aspartate α-decarboxylase (EC 4.1.1.11) (ADC) for the production of β-alanine was studied. With an increasing activity up to 90 °C and maintaining its activity upon storage for 24 hours at 60 °C, ADC showed a remarkably high thermostability. ADC has an optimum at pH 7.5 and starts to lose activity upon storage below pH 6. An inhibiting effect by β-alanine was not observed. Immobilization on Sepabeads EC-EP and EC-HFA epoxy supports did not result in an increased thermostability, but did improve operational stability. Nonetheless, enzyme inactivation occurs during catalysis, probably caused by irreversible transamination of the catalytically essential pyruvoyl group. The Royal Society of Chemistry 2009.

Metal Promoted Cleavage of Diethylenetriamine to give β-Alanine

Bernardi, Roberta,Zanotti, Matteo,Bernardi, Giovanni,Duatti, Adriano

, p. 1015 - 1016 (1992)

An unusual, facile cleavage of C-N bonds of diethylenetriamine (H2NCH2CH2NHCH2CH2NH2 = dien) promoted by the reaction with the rhenium(V) nitrido complex to yield β-alanine (H2NCH2CH2CO2H = β-ala) is reported.

FORMATION OF AMINO ACIDS IN THE SHOCK-WAVE COMPRESSION OF THE AMMONIUM SALTS OF UNSATURATED ACIDS

Zharov, A. A.,Adadurov, G. A.,Kazakevich, A. G.,Zhulin, V. M.,Yakovleva, I. I.

, p. 1104 (1984)

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OXIDATIVE DEGRADATION OF β- AND γ-AMINO ACIDS BY CONTACT GLOW DISCHARGE ELECTROLYSIS

Harada, Kaoru,Terasawa, Jun-ichi

, p. 441 - 444 (1980)

The degradation of β- and γ-amino acids in aqueous solutions by contact glow discharge electrolysis (CGDE) was studied.It was found that the reaction is actually a stepwise oxidative degradation by hydroxyl radical produced by CGDE.

Amination of Carboxylic Acids by Reductive Fixation of Molecular Nitrogen by Glow Discharge Against Aqueous Solution

Harada, Kaoru,Igari, Shun-ichiro,Munegumi, Toratane,Takasaki, Michiaki,Shimoyama, Akira

, p. 1776 - 1781 (1991)

Amination of several carboxylic acids by reductive fixation of molecular nitrogen was achieved by glow discharge against aqueous solution of these carboxylic acids.The yield of the aminated product is the highest in the case of maleic acid among carboxylic acids used.The addition of hydrochloric acid to the reaction mixture enhances the yield of aminated products.This may be caused by the fact that chloride anion is oxidized by hydroxyl radicals to chlorate ion, and the fixation of molecular nitrogen proceeds under relatively reducing conditions.

Efficient biosynthesis of β-alanine with a tandem reaction strategy to eliminate amide by-product in the nitrilase-catalyzed hydrolysis

Tao, Yanyang,Han, Chao,Wang, Min,Yao, Peiyuan,Yuan, Jing,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming

, p. S60 - S67 (2016)

An efficient biosynthesis of β-alanine from 3-aminopropionitrile at high concentration has been developed using a one-pot bienzymatic cascade of a nitrilase and an amidase. The nitrilase BjNIT3397 from Bradyrhizobium japonicum strain USDA110 catalyzes the hydrolysis of 3-aminopropionitrile to β-alanine at the concentration up to 3.0 mol/L with the formation 23% of 3-aminopropanamide. In order to eliminate the by-product 3-aminopropanamide, we cloned and characterized a new amidase from Pseudomonas nitroreducens through gene mining. Under the optimal conditions (50 mmol/L Na2HPO4-NaH2PO4 buffer, pH 6.0, 40 °C), 2.0 mol/L (176 g/L) of 3-aminopropanamide was completely hydrolyzed within 12 h. A tandem reaction system was then established to eliminate the by-product 3-aminopropanamide and increase the production of β-alanine to 90% isolated yield with 15.02 g/(L.h) space-time-yield. These results demonstrated that the tandem reaction strategy was an effective method of eliminating the amide by-products in the nitrilase-catalyzed hydrolysis at high substrate concentration.

Oxidation reaction of aliphatic amines and aminoalcohols in aqueous solution induced by argon arc plasma

Takasaki, Michiaki,Harada, Kaoru

, p. 4463 - 4473 (1985)

Argon arc plasma induced a powerful and stepwise oxidation reaction including conversion of methyl group to carboxyl group, oxidative cleavage of carbon-carbon bond, and oxidative deamination. Main active species were considered to be hydroxyl radicals by decomposition of water molecules.

Stereochemistry of Catabolism of the RNA Base Uracil

Gani, David,Young, Douglas W.

, p. 1355 - 1362 (1985)

A mammalian enzyme system has been used to study the stereochemistry of the catabolism of the pyrimidine uracil (1) to the amino acid β-alanine (4).Use of - and - uracils and of (2)H2O in the incubations yielded sterospecifically deuteriated samples of β-alanine.Assays, involving total synthesis of samples of β-alanine unambigously labelled with deuterium in each of the four C-H bonds have shown that, in the first step in the catabolic process, uracil is reduced by dihydrouracil dehydrogenase with overall anti addition of hydrogen, at the si face at C-6 and the si face at C-5.

REACTION OF ATOMIC CARBON WITH AMMONIA. THE MECHANISM OF FORMATION OF AMINO ACID PRECURSORS.

Shevlin,McPherson,Melius

, p. 488 - 491 (1983)

The reaction of arc-generated carbon atoms with ammonia have been investigated. Primary reactions of C//1 are NH insertion and hydrogen abstraction. The NH insertion leads to methyleneamine (1) and HCN. The hydrogen abstraction proceeds in a stepwise manner to generate CH//2, which reacts with NH//3 to produce CH//3NH//2. Hydrolysis of the nonvolatile residue from this reaction produces the amino acids glycine, alanine, N-methylglycine, beta -alanine, and aspartic acid. Serine is also formed when H//2O is included with the reactants. The mechanism of formation of the amino acid precursors is discussed. Labeling experiments (**2H and **1**3C) rule out a hydrogen cyanide polymer as a major precursor to the amino acids. These studies may provide information on extraterrestrial amino acids. Refs.

CHEMICAL TRANSFORMATIONS OF SOLID ORGANIC COMPOUNDS UPON HIGH-PRESSURE EXTRUSION

Bogdanov, A. Yu.,Zharov, A. A.,Zhulin, V. M.

, p. 233 (1986)

-

RADIATION STABILITY OF AQUEOUS SOLUTIONS OF VITAMIN B3

Barelko, E. V.,Babakina, G. S.,Rakitskaya, G. A.,Solyanina, I. P.,Tal'roze, V. L.,et al.

, p. 405 - 406 (1980)

-

Kinetics of oxidation of pantothenic acid by chloramine-T in perchloric acid and in alkaline medium catalyzed by OsO4: A mechanistic approach

Puttaswamy,Jagadeesh

, p. 201 - 210 (2005)

Kinetics of oxidation of pantothenic acid (PA) by sodium N-chloro-p-toluenesulfonamide or chloramine-T (CAT) in the presence of HClO 4 and NaOH (catalyzed by OsO4) has been investigated at 313 K. The stoichiometry and oxidation products are same in both media; however, their kinetic patterns were found to be different. In acid medium, the rate shows first-order dependence on |CAT|o, fractional-order dependence on |PA|o, and inverse fractional-order on |H+|. In alkaline medium, the rate shows first-order dependence each on |CAT| o and |PA|o and fractional-order dependence on each of |OH-| and |OsO4|. Effects of added p-toluenesulfonamide and halide ions, varying ionic strength, and dielectric constant of medium as well as solvent isotope on the rate of reaction have been investigated. Activation parameters were evaluated, and the reaction constants involved in the mechanisms have been computed. The proposed mechanisms and the derived rate laws are consistent with the observed kinetics.

Photolytic release of bioactive carboxylic acids from fused pyran conjugates

Concei??o, Rafaela,Hungerford, Graham,Costa, Susana P.G.,Gon?alves, M. Sameiro T.

, p. 368 - 379 (2018)

New ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiation in a RPR-100 photochemical reactor. The processes were followed by HPLC-UV detection and 1H NMR with collection of kinetic data. The results showed a correlation between the photolysis efficiency and the increasing extension of the conjugation for both glycine and β-alanine, showing that the 7-aminocoumarin afforded the best results at all wavelengths tested. From a study of the time-resolved fluorescence behaviour, these compounds were also found to exhibit more complex fluorescence decay kinetics. This was attributed to the presence of conjugated and non-conjugated coumarin species.

-

Breslow et al.

, p. 3760,3762 (1957)

-

Catalytic reaction of model zinc(II) complex for active sites of mono-nuclear zinc-peptidases

Ogawa, Kazuya,Nakata, Kou,Ichikawa, Kazuhiko

, p. 797 - 798 (1998)

Catalytic hydrolysis reaction of amide by designed zinc-complex model for active sites of mono-nuclear zinc-peptidases has been investigated. The effect of carboxylate ligand of the model complex on hydrolysis activity was revealed by kinetic analyses.

Recycling method of beta,beta-iminodipropionitrile and application

-

Paragraph 0093; 0096-0097; 0122; 0125-0126, (2021/05/26)

The invention provides a recycling method of beta,beta-iminodipropionitrile and application, and relates to the technical field of waste recycling. According to the recycling method, by adopting a specific reaction synthesis route, the beta,beta-iminodipropionitrile finally generates calcium pantothenate with wide application, and the recycling method not only reduces hazardous waste emission and treatment and lowers the hazardous waste treatment cost, but also realizes the purpose of turning waste into wealth from beta,beta-iminodipropionitrile, and the utilization value of beta,beta-iminodipropionitrile is greatly improved. The invention further provides application of the recycling method of the beta,beta-iminodipropionitrile, and in view of the advantages of the recycling method of the beta,beta-iminodipropionitrile, a new process route is provided for preparing calcium pantothenate.

Development and Application of Efficient Ag-based Hydrogenation Catalysts Prepared from Rice Husk Waste

Unglaube, Felix,Kreyenschulte, Carsten Robert,Mejía, Esteban

, p. 2583 - 2591 (2021/04/09)

The development of strategies for the sustainable management and valorization of agricultural waste is of outmost importance. With this in mind, we report the use of rice husk (RH) as feedstock for the preparation of heterogeneous catalysts for hydrogenation reactions. The catalysts were prepared by impregnating the milled RH with a silver nitrate solution followed by carbothermal reduction. The composition and morphology of the prepared catalysts were fully assessed by IR, AAS, ICP-MS, XPS, XRD and STEM techniques. This novel bio-genic silver-based catalysts showed excellent activity and remarkable selectivity in the hydrogenation of nitro groups in both aromatic and aliphatic substrates, even in the presence of reactive functionalities like halogens, carbonyls, borate esters or nitriles. Recycling experiments showed that the catalysts can be easily recovered and reused multiple times without significant drop in performance and without requiring re-activation.

A plug-and-play chemobiocatalytic route for the one-pot controllable synthesis of biobased C4 chemicals from furfural

Huang, Yi-Min,Lu, Guang-Hui,Zong, Min-Hua,Cui, Wen-Jing,Li, Ning

supporting information, p. 8604 - 8610 (2021/11/16)

Chemobiocatalytic selective transformation is an attractive yet challenging task, due to the incompatibility issues between different types of catalysts. In this work, one-pot, multi-step cascades integrating biocatalysis with organo-, base- and photocatalysis in a plug-and-play fashion were constructed for the controllable synthesis of eight C4 chemicals from furfural. Furfural was converted to 5-hydroxy-2(5H)-furanone (HFO) by sequential biocatalytic oxidation and photooxygenation in phosphate buffer, in >90% yields. Ring opening and concurrent isomerization of HFO to fumaric semialdehyde (FSA) were readily realized under mild conditions by a weakly basic resin (e.g., DVB resin). The versatile intermediate FSA could be oxidized to fumaric acid (FA) using a laccase-2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO) system, which was further upgraded to amino acids including l-aspartic acid (l-Asp) and β-alanine (β-Ala) by whole-cell catalysis. Notably, amino acids were obtained from biobased furfural in a one-pot, four-step process with yields of up to 75%, without the isolation of any intermediates. Besides, the scale-up synthesis of l-Asp was demonstrated. This work demonstrates the great potential of the combination of chemo- and biocatalysis for selective furfural valorization.

Genomics-driven discovery of a new cyclodepsipeptide from the guanophilic fungusAmphichorda guana

Liang, Min,Lyu, Hai-Ning,Ma, Zi-Ying,Li, Er-Wei,Cai, Lei,Yin, Wen-Bing

, p. 1960 - 1964 (2021/03/16)

Two potential non-ribosomal peptide synthetases (NRPSs) were identified in the genome of a guanophilic fungusAmphichorda guanaby bioinformatics analysis and gene knockout experiments. Liquid chromatography coupled with mass spectrometry (LC-MS) guided isolation led to the discovery of a new cyclodepsipeptide isaridin H (1) and seven known analogs, desmethylisaridin E (2), isaridin E (3), isariin A (4), iso-isariin B (5), iso-isariin D (6), isariin E (7), and nodupetide (8). The absolute configuration of isaridin H (1) was achieved by Marfey's method. Isaridin H (1) showed significant antifungal activity againstBotrytis cinereaandAlternaria solani.

Expanding the repertoire of nitrilases with broad substrate specificity and high substrate tolerance for biocatalytic applications

Rayavarapu, Pratima,Shah, Shikha,Sunder, Avinash Vellore,Wangikar, Pramod P.

, p. 289 - 296 (2020/05/18)

Enzymatic conversion of nitriles to carboxylic acids by nitrilases has gained significance in the green synthesis of several pharmaceutical precursors and fine chemicals. Although nitrilases from several sources have been characterized, there exists a scope for identifying broad spectrum nitrilases exhibiting higher substrate tolerance and better thermostability to develop industrially relevant biocatalytic processes. Through genome mining, we have identified nine novel nitrilase sequences from bacteria and evaluated their activity on a broad spectrum of 23 industrially relevant nitrile substrates. Nitrilases from Zobellia galactanivorans, Achromobacter insolitus and Cupriavidus necator were highly active on varying classes of nitriles and applied as whole cell biocatalysts in lab scale processes. Z. galactanivorans nitrilase could convert 4-cyanopyridine to achieve yields of 1.79 M isonicotinic acid within 3 h via fed-batch substrate addition. The nitrilase from A. insolitus could hydrolyze 630 mM iminodiacetonitrile at a fast rate, effecting 86 % conversion to iminodiacetic acid within 1 h. The arylaliphatic nitrilase from C. necator catalysed enantioselective hydrolysis of 740 mM mandelonitrile to (R)-mandelic acid in 4 h. Significantly high product yields suggest that these enzymes would be promising additions to the suite of nitrilases for upscale biocatalytic application.

Process route upstream and downstream products

Process route

β-Ala-OPNP
87880-78-2

β-Ala-OPNP

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With Cu complex of polymer from 2,6-bis-aminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane; water; In dimethyl sulfoxide; at 25 ℃; Rate constant; var.reag.: Cu(2+) complex of 2,6-bis-benzylaminomethylpyridine; oligomers of 2,6-bis-aminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane;
deoxythymidylyl-(5'->N)-β-alanine
85590-80-3

deoxythymidylyl-(5'->N)-β-alanine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With hydrogenchloride; water; at 37 ℃; for 1h; Product distribution; hydrolytic stability at various pH;
leucinostatin A
82111-44-2

leucinostatin A

(2S,3S)-3-hydroxyleucine
10148-70-6

(2S,3S)-3-hydroxyleucine

cis-4-methyl-(S)-proline
6734-41-4

cis-4-methyl-(S)-proline

2-Aminoisobutyric acid
62-57-7

2-Aminoisobutyric acid

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With hydrogenchloride; at 110 ℃; for 20h; Further byproducts given;
leucinostatin A
82111-44-2

leucinostatin A

(2S,3S)-3-hydroxyleucine
10148-70-6

(2S,3S)-3-hydroxyleucine

2-Aminoisobutyric acid
62-57-7

2-Aminoisobutyric acid

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With hydrogenchloride; at 110 ℃; for 20h; Further byproducts given;
2-Amino-1-propanol
6168-72-5

2-Amino-1-propanol

(RS)-isoserine
632-12-2

(RS)-isoserine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
In water; at 10 - 20 ℃; Yield given. Further byproducts given. Yields of byproduct given; contact glow discharge electrolysis;
In water; at 10 - 20 ℃; Yield given. Further byproducts given. Yields of byproduct given; contact glow discharge electrolysis, pH=2.7;
In water; at 10 - 20 ℃; Yield given. Further byproducts given; contact glow discharge electrolysis, pH=2.7;
2-Amino-1-propanol
6168-72-5

2-Amino-1-propanol

(RS)-isoserine
632-12-2

(RS)-isoserine

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
In water; at 10 - 20 ℃; Product distribution; pH=2.7 and pH=12.0, various reaction times, contact glow discharge electrolysis;
C<sub>6</sub>H<sub>11</sub>N<sub>2</sub>O<sub>3</sub><sup>(1-)</sup>*Na<sup>(1+)</sup>
64371-16-0

C6H11N2O3(1-)*Na(1+)

sodium β-alaninate
16690-93-0

sodium β-alaninate

disodium iminodipropionate

disodium iminodipropionate

3-(3-Amino-propionylamino)-propionic acid
2140-53-6

3-(3-Amino-propionylamino)-propionic acid

di(2-carboxyethyl)amine
505-47-5

di(2-carboxyethyl)amine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With Amberlyst 15; In water;
3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

di(2-carboxyethyl)amine
505-47-5

di(2-carboxyethyl)amine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With ammonia; water;
3-iodopropanoic acid
141-76-4

3-iodopropanoic acid

di(2-carboxyethyl)amine
505-47-5

di(2-carboxyethyl)amine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With ammonia;
acrylic acid
79-10-7

acrylic acid

di(2-carboxyethyl)amine
505-47-5

di(2-carboxyethyl)amine

monoammonium salt of β,β'-iminodipropionic acid
16675-33-5

monoammonium salt of β,β'-iminodipropionic acid

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
Conditions Yield
With ammonium hydroxide; at 100 ℃; Kinetics; Rate constant; in the presence of KOH or HCl;

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