21685-37-0Relevant academic research and scientific papers
Enhanced Cyclization of N-Benzyloxycarbonyl-N-substituted Dipeptide Methyl Esters with Ammonia
Kawashiro, Katsuhiro,Nishiguchi, Kazuhisa,Kurosaka, Ikuo
, p. 2404 - 2406 (2007/10/02)
Cyclization of N,N'- dimethyl ester to the hydantoin derivative took place easily under mild ammonolysis conditions.Replacement of Z by p-methoxy-benzyloxycarbonyl also led to the cyclizatio
PEPTIDE BOND FORMATION BY INTERMOLECULAR AMINOLYSIS OF D-GLUCOPYRANOSYL ESTERS OF AMINO ACIDS
Horvat, Stefica,Keglevic, Dina
, p. 89 - 96 (2007/10/02)
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.
