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10065-72-2

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10065-72-2 Usage

Chemical Properties

white crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 10065-72-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,0,6 and 5 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 10065-72:
(7*1)+(6*0)+(5*0)+(4*6)+(3*5)+(2*7)+(1*2)=62
62 % 10 = 2
So 10065-72-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H9NO2/c1-3(5)4(6)7-2/h3H,5H2,1-2H3

10065-72-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl L-alaninate

1.2 Other means of identification

Product number -
Other names alanine methyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10065-72-2 SDS

10065-72-2Relevant articles and documents

Accelerated tert-butyloxycarbonyl deprotection of amines in microdroplets produced by a pneumatic spray

Fedick, Patrick W.,Bain, Ryan M.,Bain, Kinsey,Mehari, Tsdale F.,Cooks, R. Graham

, p. 98 - 103 (2018)

Protection and deprotection of organic compounds in multistep reactions using functional groups such as tert-butoxycarbonyl (Boc), is widely performed in synthetic organic chemistry. Reaction rate acceleration studies in spray-based ionization methods (electrosonic spray, paper spray, nanospray) have become increasingly common. Here, we demonstrate reaction rate acceleration of Boc deprotection using easy ambient sonic-spray ionization (EASI), a pneumatic technique which does not involve an applied voltage, in a teaching laboratory setting. The goal of this laboratory exercise was to explore acceleration in a previously unexplored spray-based reaction, while emphasizing in a pedagogic setting the importance of protecting groups for multistep synthesis. Rate acceleration factors of more than an order of magnitude were observed in the uncharged micron-sized droplets generated by EASI. The effect of reaction conditions on reaction acceleration was examined including changes in the type of acid, reagent concentration ratios and syringe pump flow rates. Student knowledge was assessed by pre-laboratory assignments, post-laboratory reports and oral interviews.

In situ deprotection and incorporation of unnatural amino acids during cell-free protein synthesis

Arthur, Isaac N.,Hennessy, James E.,Padmakshan, Dharshana,Stigers, Dannon J.,Lesturgez, Stéphanie,Fraser, Samuel A.,Liutkus, Mantas,Otting, Gottfried,Oakeshott, John G.,Easton, Christopher J.

, p. 6824 - 6830 (2013)

The S30 extract from E. coli BL21 Star (DE3) used for cell-free protein synthesis removes a wide range of α-amino acid protecting groups by cleaving α-carboxyl hydrazides; methyl, benzyl, tert-butyl, and adamantyl esters; tert-butyl and adamantyl carboxamides; α-amino form-, acet-, trifluoroacet-, and benzamides and sidechain hydrazides and esters. The free amino acids are produced and incorporated into a protein under standard conditions. This approach allows the deprotection of amino acids to be carried out in situ to avoid separate processing steps. The advantages of this approach are demonstrated by the efficient incorporation of the chemically intractable (S)-4-fluoroleucine, (S)-4,5- dehydroleucine, and (2S,3R)-4-chlorovaline into a protein through the direct use of their respective precursors, namely, (S)-4-fluoroleucine hydrazide, (S)-4,5-dehydroleucine hydrazide, and (2S,3R)-4-chlorovaline methyl ester. These results also show that the fluoroand dehydroleucine and the chlorovaline are incorporated into a protein by the normal biosynthetic machinery as substitutes for leucine and isoleucine, respectively. Copyright

Synthesis of α-Amino Acids by Reduction of α-Oximino Esters with Titanium(III) Chloride and Sodium Borohydride

Hoffman, Christopher,Tanke, Robin S.,Miller, Marvin J.

, p. 3750 - 3751 (1989)

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Photochemical desulfurization of L-cysteine derivatives

Gonzalez, Asensio,Valencia, Gregorio

, p. 2761 - 2764 (1998)

Thiol groups can be reductively eliminated at room temperature by a photochemical method which makes use of triethylboron, triethylphosphite and visible light. Thus, after treating L-Cys 1a, D-Pen 1b, L-Cys-OMe 1c and glutathione (γ-L-Glu-L-Cys-Gly) 3, the corresponding desulfurized compounds L-Ala 2a, D-Val 2b, L-Ala-OMe 2c and γ-L-Glu-L-Ala-Gly 4, respectively, are prepared in high yields and with retention of configuration.

A New Set of Isoreticular, Homochiral Metal-Organic Frameworks with ucp Topology

Sartor, Michael,Stein, Timo,Hoffmann, Frank,Fr?ba, Michael

, p. 519 - 528 (2016)

A new isoreticular series of metal-organic frameworks, called UHM-25 (UHM: University of Hamburg Materials), based on the copper paddle wheel motif and a novel set of homochiral linkers has been synthesized. Starting from amino acids available from the chiral pool a synthesis procedure was established that allows a straightforward, multigram scale synthesis of homochiral linkers in 4-5 steps. These linkers carry substituents that have been proven useful in stereoselective organic chemistry, such as the Evans auxiliary or chiral amino alcohols. The resulting MOFs only differ in the chiral moiety provided by the amino acid starting material. The structure of UHM-25 is composed of cuboctahedral cages of Cu2 paddle wheel motifs connected by the isophthalate moieties of the linker. These cages are linked via the bent backbone of the linker resulting in a primitive cubic arrangement, giving rise to the rare underlying (3,4)-c binodal net ucp. MOFs of the UHM-25 series show surface areas up to SBET = 1900 m2/g. Postsynthetic modification reactions with excellent conversion rates confirmed the accessibility to the chiral groups. Furthermore, UHM-25-Pro bearing a prolinol functionality was used in a self-directed, enantioselective aldol addition of acetaldehyde, demonstrating the potential of the UHM-25 series with regard to heterogeneous, stereoselective catalysis.

Crystallographic insight-guided nanoarchitectonics and conductivity modulation of an n-type organic semiconductor through peptide conjugation

Pandeeswar,Khare, Harshavardhan,Ramakumar, Suryanarayanarao,Govindaraju

, p. 8315 - 8318 (2015)

Crystallographic insight-guided nanoarchitectonics of peptide-conjugated naphthalene diimide (NDI) is described. In a bio-inspired approach, non-proteinogenic α-amino isobutyric acid (Aib)- and alanine (Ala)-derived peptides orchestrated the 1D achiral and 2D chiral molecular ordering of NDI, respectively, which resulted in modulation of nanoscale morphology, chiroptical and conductivity properties.

Chiral iminoesters derived from d-glyceraldehyde in [3+2] cycloaddition reactions. Asymmetric synthesis of a key intermediate in the synthesis of neuramidinase inhibitors

Galvez, Jose A.,Diaz-De-Villegas, Maria D.,Alias, Miriam,Badorrey, Ramon

, p. 11404 - 11413 (2013)

Silver-catalyzed endo-selective and copper-catalyzed exo-selective asymmetric [3 + 2] cycloadditions of acrylates to chiral iminoesters derived from d-glyceraldehyde have been investigated. The reaction diastereoselectively provides highly functionalized pyrrolidines. This approach was used to develop the first asymmetric synthesis of a key intermediate in the synthesis of pyrrolidine influenza neuramidinase inhibitors.

Chiral phosphorescent probes for amino acids: hybrids of iridium(iii) complexes with synthetic saponite

Sato, Hisako,Tamura, Kenji,Yajima, Tomoko,Sato, Fumi,Yamagishi, Akihiko

, p. 2780 - 2785 (2017)

An attempt of developing a chiral luminescent probe for amino acids was described. Two types of chiral iridium(iii) complexes were synthesized: [Ir(dfppy)2(R-pep-bpy)]+ (dfppyH = 2-(2′,4′-difluorophenyl)pyridine); R-pep-bpy = 4,4′-bis((R-1,2-dimethylpropyl)aminocarbonyl-2,2′-bipyridine) and [Ir(piq)2(R-pep-bpy)]+ (piqH = 1-phenyisoquinoline). In both complexes, amido groups (R-pep-) were attached to 2,2′-bipyridine with an intension of increasing the affinity for an amino acid. The complexes were optically resolved on a chiral column. When the complexes were adsorbed by the colloidal particles of synthetic saponite, they were highly emissive even in a medium containing water. The remarkable quenching of emission was observed for the combination of [Ir(dfppy)2(R-pep-bpy)]+ and tryptophan methyl ester. By the use of the enantiomeric complexes, the possibility of enantioselective quenching was examined for various amino acid derivatives.

Phosphorylthioureas and phosphorylureas containing amino acid fragments

Shipov,Genkina,Petrovskii

, p. 2512 - 2516 (2009)

A series of (dialkoxyphosphoryl)thioureas and their 1,3,2-oxazaphosphinane analogs containing fragments of glycine, alanine, ss-alanine, L-aspartic and L-glutamic acids, as well as phosphorylureas derived from glycine and ss-alanine were synthesized in the search for potential biologically active compounds (including possible inhibitors of aspartate trans-carbamoylase).

New strategies for an efficient removal of the 9- fluorenylmethoxycarbonyl (Fmoc) protecting group in the peptide synthesis

Leggio, Antonella,Liguori, Angelo,Napoli, Anna,Siciliano, Carlo,Sindona, Giovanni

, p. 573 - 575 (2000)

The aluminium trichloride/toluene system is investigated as a novel, unusual and straightforward reagent for the removal of the 9- fluorenylmethoxycarbonyl (Fmoc) protecting group in the solution peptide synthesis. This procedure avoids any undesired side reactions, such as the frequently observed inversion of the amino acid configuration.

Concentration-dependent dye aggregation and disassembly triggered by the same artificial helical foldamer

Qiu, Yuan,Hu, Haisi,Zhao, Dongxu,Wang, Jing,Wang, Hong,Wang, Qin,Peng, Haiyan,Liao, Yonggui,Xie, Xiaolin

, p. 7 - 15 (2019)

Constructing and regulating the cyanine dye aggregates have been constantly pursued because of their wide applications in photosensitizers, biological fluorescence probes, nonlinear optics, etc. However, to realize such a process using a single additive still remains a formidable challenge. Here, the aggregation and disassembly of positively charged 3,3-diethyloxadicarbocyanine iodide (DiOC2(5)) have been demonstrated just by changing the concentration of an artificial poly(phenylenediethynylene)-based helical foldamer (Poly-1) bearing L-alanine sodium pendants with an amide linker. Poly-1 possessed the negatively charged pendants and hydrophobic helical grooves. Upon simple mixing of equal DiOC2(5) and Poly-1, DiOC2(5) molecules were mainly enriched on Poly-1 surface driven by electrostatic interaction and arranged along the main chain of Poly-1, resulting in the formation of chiral H-aggregates. But, the excessive Poly-1 would attract some DiOC2(5) molecules in H-aggregates via electrostatic interaction. The isolated monomers were easy to orderly disperse into the helical grooves due to hydrophobic interaction. Meanwhile, during the aggregation and disassembly, the solution color changed from peachblow to purple red and then to purple and finally to navy blue.

Imines derived from 4-methyl-4-diphenylphosphorylpentan-2-one and potassium salts of aminocarboxylic acids

Dimukhametov,Mironov,Tatarinov

, (2017)

An effective procedure for the preparation of imines based on 4-methyl-4-diphenylphosphorylpentan-2-one, aminoacetic, aminopropionic, and aminobutyric acids with yields of 90–95% was developed. Reaction of dimephosphone (4-methyl-4-dimethoxyphosphorilpent

A Facile Synthesis of α-Amino Esters via Reduction of α-Nitro Esters Using Ammonium Formate as a Catalytic Hydrogen Transfer Agent

Ram, Siya,Ehrenkaufer, Richard E.

, p. 133 - 135 (1986)

Various nitroesters 3 were selectively and rapidly reduced to their corresponding amino esters 4 in very good yield using anhydrous ammonium formate as a catalytic hydrogen transfer agent.

Synthesis and molecular recognition of novel multiimidazole cyclophanes

Xu, Xiao-Wei,Wang, Xin-Long,Wu, Ai-Ming,Zheng, Zhi-Ming,Yi, Mei-Gui,Xiao, Rong

, p. 1137 - 1141 (2009)

(Chemical Equation Presented) Cyclophanes based on 2,2′-biimidazole and 2,2′-bibenzimidazole were synthesized as receptors. UV spectroscopic titration in chloroform at 25°C showed 1:1 complexes between the cyclophanes and the guests, and the binding constants (K) and Gibbs free energy changes (-ΔG0) were calculated according to the modified Benesi-Hildebrand equation.

New Amino-Acid-Based β-Phosphorylated Nitroxides for Probing Acidic pH in Biological Systems by EPR Spectroscopy

Thétiot-Laurent, Sophie,Gosset, Ga?lle,Clément, Jean-Louis,Cassien, Mathieu,Mercier, Anne,Siri, Didier,Gaudel-Siri, Anouk,Rockenbauer, Antal,Culcasi, Marcel,Pietri, Sylvia

, p. 300 - 315 (2017)

There is increasing interest in measuring pH in biological samples by using nitroxides with pH-dependent electron paramagnetic resonance (EPR) spectra. Aiming to improve the spectral sensitivity (ΔaX) of these probes (i.e., the difference between the EPR hyperfine splitting (hfs) in their protonated and unprotonated forms), we characterized a series of novel linear α-carboxy, α′-diethoxyphosphoryl nitroxides constructed on an amino acid core and featuring an (α or α′)-C?H bond. In buffer, the three main hfs (aN, aH, and aP) of their EPR spectra vary reversibly with pH and, from aP or aH titration curves, a two- to fourfold increase in sensitivity was achieved compared to reference imidazoline or imidazolidine nitroxides. The crystallized carboxylate 10 b (pKa ≈3.6), which demonstrated low cytotoxicity and good resistance to bioreduction, was applied to probe stomach acidity in rats. The results pave the way to a novel generation of highly sensitive EPR pH markers.

Ceric ammonium nitrate (CAN) mediated esterification of N-Boc amino acids allows either retention or removal of the N-Boc group

Kuttan, Ashani,Nowshudin, Shiek,Rao

, p. 2663 - 2665 (2004)

Reaction of N-Boc amino acids with ceric ammonium nitrate in an alcohol as the solvent at room temperature resulted in the esterification of N-Boc amino acids with Boc group retention. When the reaction was conducted at reflux temperature, esterification was accompanied with simultaneous removal of the Boc group. Both reactions gave the desired products in good yields.

Appel,Hauss

, p. 290,300 (1961)

Deprotection/reprotection of the amino group in α-amino acids and peptides. A one-pot procedure in [Bmim][BF4] ionic liquid

Di Gioia,Barattucci,Bonaccorsi,Leggio,Minuti,Romio,Temperini,Siciliano

, p. 2678 - 2686 (2014)

This paper presents an efficient one-pot protocol for the sequential deprotection/reprotection of the α-amino group in α-amino acid and dipeptide methyl esters. [Bmim][BF4] is used as the solvent in the entire process. In particular, the use of the ionic liquid allows for rapid and clean removal of the 4-nitrobenzenesulfonyl (nosyl) group and for facile subsequent tert-butyloxycarbonylation of the free α-amino function under very mild conditions. N-Boc-α-amino acid as well as peptide derivatives are isolated in excellent yields, and do not require any further purification. Absolute configurations of the precursors are totally preserved during the process.

Controlled drug delivery from mesoporous silica using a pH-response release system

Jin, Dalsaem,Lee, Ji Ha,Seo, Moo Lyong,Jaworski, Justyn,Jung, Jong Hwa

, p. 1616 - 1620 (2012)

Mesoporous hollow silica nanoparticles were functionalized with phenanthroline (P-MHS) to prepare a carrier for a host-guest complex. Curcumin was selected as a model drug molecule. The phenanthroline attached to the P-MHS was complexed with Cu2+ through a coordination bond. When the Cu 2+-P-MHS was exposed to ~pH 5, the curcumin was efficiently released into the aqueous phase within 120 min. This work describes a method for functionalizing the surface of the porous silica nanoparticles in a well-defined manner. The P-MHS carrier exhibited controlled release of a model drug under acidic pH conditions.

Asakura et al.

, p. 467 (1979)

Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host?Guest Complexes with a Bis(zinc porphyrin) Tweezer

Olsson, Sandra,Sch?fer, Clara,Blom, Magnus,Gogoll, Adolf

, p. 1169 - 1178 (2018)

A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 : 10 to 1 : 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1 : 2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

Synthesis and biological evaluation of novel lipoamino acid derivatives

Kaki, Shiva Shanker,Arukali, Sammaiah,Korlipara, Padmaja V.,Prasad,Yedla, Poornachandra,Ganesh Kumar

, p. 209 - 212 (2016)

Seven novel lipoamino acid conjugates were synthesized from methyl oleate and amino acids. Methyl oleate was grafted to different amino acids using thioglycolic acid as a spacer group. Seven derivatives (3a-g) were prepared and characterized by spectral data (NMR, IR and MS spectral studies). All the derivatives were studied for their antimicrobial, anti-biofilm and anticancer activities. Among all the derivatives, it was found that compound 3b was the most potent antibacterial compound which showed good activity against four Gram positive bacterial strains and also exhibited excellent antifungal activity against a fungal strain. In the anti-biofilm assay, compound 3b showed promising activity with IC50 value of 2.8 μM against Bacillus subtilis MTCC 121. All the compounds showed anticancer activities with 3c showing promising anticancer activity (IC50 = 15.3-22.4 μM) against the four cell lines tested.

A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters

Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther

supporting information, p. 2099 - 2102 (2021/07/22)

A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of α-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl]2. Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.

Design, synthesis and evaluation of the antibacterial activity of new Linezolid dipeptide-type analogues

García-Olaiz,Alcántar-Zavala, Eleazar,Ochoa-Terán, Adrián,Cabrera, Alberto,Mu?iz-Salazar, Raquel,Montes-ávila, Julio,Salazar-Medina, Alex J.,Alday, Efrain,Velazquez, Carlos,Medina-Franco, José L.,Laniado-Laborín, Rafael

supporting information, (2019/12/23)

Worldwide studies towards development of new drugs with a lower rate in emergence of bacterial resistance have been conducted. The molecular docking analysis gives a possibility to predict the activity of new compounds before to perform their synthesis. In this work, the molecular docking analysis of 64 Linezolid dipeptide-type analogues was performed to predict their activity. The most negative scores correspond to six Fmoc-protected analogues (9as, 9bs, 9bu, 10as, 10ax and 10ay) where Fmoc group interacts in PTC for Linezolid. Twenty-six different Fmoc-protected Linezolid dipeptide-type analogues 9(as-bz) and 10(as-bz) were synthesized and tested in antimicrobial experiments. Compounds 9as, 9ay, 9ax, 10as, 10ay and 9bu show significant activity against group A Streptococcus clinical isolated. Analogue 10ay also display high activity against ATCC 25923 Staphylococcus aureus strain and MRSA-3, MRSA-4 and MRSA-5 clinical isolates, with MIC values lower than Linezolid. The highest activity against multidrug-resistant clinical isolates of Mycobacterium tuberculosis was exhibited by 9bu. Finally, a cytotoxicity assay with ARPE-19 human cells revealed a non-cytotoxic effect of 9bu and 10ay at 50 and 25 μM, respectively.

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