108258-31-7

Basic information

• Product Name: D-ASPARAGINE METHYL ESTER
• Synonyms: D-ASPARAGINE METHYL ESTER;H-D-ASN-OME;(R)-Methyl 2,4-diaMino-4-oxobutanoate
• CAS NO: 108258-31-7
• Molecular Formula: C₅H₁₀N₂O₃
• Molecular Weight: 146.1445
• Mol File: 108258-31-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 328.5oC at 760 mmHg
• Flash Point: 198.1oC
• Appearance: /
• Density: 1.223g/cm3
• Vapor Pressure: 0.000189mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: 2-8°C
• PKA: 16.01±0.40(Predicted)
• CAS DataBase Reference: D-ASPARAGINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: D-ASPARAGINE METHYL ESTER(108258-31-7)
• EPA Substance Registry System: D-ASPARAGINE METHYL ESTER(108258-31-7)

Safety Data

• Hazardous Substances Data: 108258-31-7(Hazardous Substances Data)

Usage

Description

D-Asparagine Methyl Ester is a protected form of D-Asparagine, which is an isomer of L-Asparagine. It plays a significant role in various biological processes and has potential applications in different industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
D-Asparagine Methyl Ester is used as a building block for the synthesis of peptide antibiotics. Its role in the pharmaceutical industry is crucial as it contributes to the development of new drugs and therapies.
Used in Microbiology:
D-Asparagine Methyl Ester serves as a nitrogen source for certain bacteria, such as Saccharomyces cerevisiae, which use it for replication. This application is essential for studying bacterial growth and understanding their metabolic processes.
Used in Enzyme Inhibition:
D-Asparagine Methyl Ester acts as a competitive inhibitor of staphylococcal L-asparaginase, an enzyme that plays a role in the breakdown of the amino acid asparagine. This application is significant in the development of treatments for certain diseases, as it can help regulate enzyme activity and prevent the growth of harmful bacteria.

InChI:InChI=1/C5H10N2O3/c1-10-5(9)3(6)2-4(7)8/h3H,2,6H2,1H3,(H2,7,8)/t3-/m1/s1

Upstream product

• 124842-28-0 N^α-(tert-butoxycarbonyl)-(S)-asparagine methyl ester 
• 67-56-1 methanol 
• 7536-55-2 N-tert-butyloxycarbonylasparagine 
• 4668-37-5 N-(benzyloxycarbonyl)asparagine methyl ester 

Downstream Products

• 1620161-89-8 (6S,9S,15S)-methyl 15-(2-amino-2-oxoethyl)-6,9-dibenzyl-2,2-dimethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate 

Relevant articles and documents

Studies on the constituents of Helleborus purpurascens: use of derivatives from calix[6]arene, homooxacalix[3]arene and homoazacalix[3]arene as extractant agents for amino acids from the aqueous extract

The task of this work was to investigate the extraction capacity of various calixarenes for free and esterified amino acids from aqueous acid phases. Furthermore, this method was applied to aqueous extracts of Helleborus purpurascens. Generally, it is known that calixarenes can be used as extractants for ammonium compounds due to π-cation and lone pair cation interactions. As first, tert-Butyl-calix[6]arene and derivatives thereof were used. They had already proven their worth in previous investigations. In addition, tert-Butyl-hexahomooxa-calix[3]arene was used also, which can also enter into lone pair cation interactions. In addition to these well-known calixarenes, new calixarenes were produced and tested. Based on the tert-Butyl-hexahomooxa-calix[3]arene, a phosphor(III)bridged derivative was prepared, combining the three aromatic hydroxyl groups to a phosphite. As a seldom-described class of calixarenes, tert-Butyl-hexahomoaza-calix[3]arene derivatives were used. The nitrogen analogues of tert-Butyl-hexahomooxa-calix[3]arene could be produced as N-benzyl derivatives. The structure of the esterified carboxymethylated derivative of N,N′,N″-Tribenzyl-tert-Butyl-hexahomoaza-calix[3]arene could be verified by X-ray structure analysis. It crystallized as a partial cone. The extraction capacity of the described calixarenes was investigated for amino acids from aqueous acidic solutions into an organic phase. For the testing were chosen asparagine, aspartic acid, tyrosine, tryptophane, phenylalanine and pipecolinic acid and their methyl esters. The amino acids and their methyl esters were dissolved in water at different pH values. The calixarenes were dissolved in dichloromethane (DCM) or chloroform. After this preparation, the aqueous acidic amino acid solutions were mixed with the solutions and shaken intensively. In addition, blank values were determined by extracting the aqueous stock solutions of the amino acids and their methyl esters with pure solvents. To determine the extraction rate, the phases were separated and each analysed using GC-FID, partially GC–MS(EI). The evaluation is performed in two ways. On the one hand the depletion in the aqueous phase and on the other hand the content in the organic phase was determined.

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

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.