7625-55-0

Basic information

• Product Name: Glycine, N-(N-acetyl-L-phenylalanyl)-, methyl ester
• CAS NO: 7625-55-0
• Molecular Formula: C14H18N2O4
• Molecular Weight: 278.308
• Mol File: 7625-55-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Glycine, N-(N-acetyl-L-phenylalanyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-(N-acetyl-L-phenylalanyl)-, methyl ester(7625-55-0)
• EPA Substance Registry System: Glycine, N-(N-acetyl-L-phenylalanyl)-, methyl ester(7625-55-0)

Safety Data

• Hazardous Substances Data: 7625-55-0(Hazardous Substances Data)

Upstream product

• 2018-61-3 (S)-2-acetylamino-3-phenylpropanoic acid 
• 26670-46-2 2-Acetylamino-3-phenyl-propionic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 616-34-2 methoxycarbonylmethylamine 
• 5680-79-5 glycine ethyl ester hydrochloride 

Downstream Products

• 29701-43-7 N-(N-acetyl-L-phenylalaninyl)glycinamide 
• 23506-38-9 N-(N-acetyl-L-phenylalanyl)glycine 

Relevant articles and documents

Postsynthetic Modification of Phenylalanine Containing Peptides by C-H Functionalization

New methods for peptide modification are in high demand in drug discovery, chemical biology, and materials chemistry; methods that modify natural peptides are particularly attractive. A Pd-catalyzed, C-H functionalization protocol for the olefination of phenylalanine residues in peptides is reported, which is compatible with common amino acid protecting groups, and the scope of the styrene reaction partner is broad. Bidentate coordination of the peptide to the catalyst appears crucial for the success of the reaction.

PEPTIDE BOND FORMATION BY INTERMOLECULAR AMINOLYSIS OF D-GLUCOPYRANOSYL ESTERS OF AMINO ACIDS

The reaction of HO-protected and -unprotected D-glucopyranosyl esters of N-acylamino acids (Gly, Ala, Phe) with glycine and phenylalanine methyl esters in N,N-dimethylformamide at 38 deg C and dichloromethane at 40 deg C, respectively, led to repture of the C-1 ester bond and formation of the corresponding N-acyldipeptide methyl ester.The relative reactivity of the C-1 ester bond toward aminolysis was greatly influenced by the structure of the amino acid nucleophile, the nature of the aglycon side-chain group, and the anomeric configuration of the D-glucopyranosyl ester involved.Evidence for a substantially lower acylating efficiency of the ester at C-2, as compared to that at C-1, was obtained by aminolysis of two fully acetylated 2-O-(acylaminoacyl)-β-D-glucopyranoses.Treatment of 1-O-(glycylglycylglycyl)-β-D-glucopyranose with phenylalanine methyl ester in N,N-dimethylformamide led to parallel hydrolysis and intermolecular aminolysis, to give the tripeptide and tetrapeptide methyl ester.