107-95-9Relevant articles and documents
On the radiochemical formation of amino acids by carboxylation and amination
Dose,Risi
, p. 581 - 587 (1968)
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Ayres
, p. 440 (1975)
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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.
An application of the Delepine reaction to beta-bromopropionic acid.
WENDLER
, p. 375 - 375 (1949)
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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.
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.
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.
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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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.
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Kuettel,McElvain
, p. 2692,2696 (1931)
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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.
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.
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Giri et al.
, p. 440,441 (1953)
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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.
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.
Poppelsdorf,Lemon
, p. 262 (1961)
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.
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.
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.
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.
CHEMICAL TRANSFORMATIONS OF SOLID ORGANIC COMPOUNDS UPON HIGH-PRESSURE EXTRUSION
Bogdanov, A. Yu.,Zharov, A. A.,Zhulin, V. M.
, p. 233 (1986)
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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.
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Breslow et al.
, p. 3760,3762 (1957)
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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.
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.
