84814-47-1

Basic information

• Product Name: glycylglycylglycyl-D,L-phenylalanine methyl ester
• Synonyms: glycylglycylglycyl-D,L-phenylalanine methyl ester
• CAS NO: 84814-47-1
• Molecular Weight: 350.374
• Mol File: 84814-47-1.mol

Chemical Properties

• CAS DataBase Reference: glycylglycylglycyl-D,L-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: glycylglycylglycyl-D,L-phenylalanine methyl ester(84814-47-1)
• EPA Substance Registry System: glycylglycylglycyl-D,L-phenylalanine methyl ester(84814-47-1)

Safety Data

• Hazardous Substances Data: 84814-47-1(Hazardous Substances Data)

Upstream product

• 15028-44-1 DL-phenylalanine methyl ester 
• 75719-94-7 1-O-(glycylglycylglycyl)-β-D-glucopyranose 

Relevant articles and documents

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.