74006-96-5Relevant academic research and scientific papers
Intermolecular Aminolyses of 1-Thioglycosyl Esters of N-Acylamino Acids
Ljevakovic, Durdica,Tomic, Srdanka,Tomasic, Jelka,Horvat, Jaroslav
, p. 1329 - 1337 (2007/10/03)
Fully acetylated 1-thioglycopyranosyl esters of N-acylamino acids (1-3), comprising different 1-thio sugars, undergo aminolysis with glycine methyl ester in dichloromethane at 40° to form the corresponding N-acyldipeptide methyl esters. The relative reactivity of the C-1 thioester bond towards aminolysis depends inter alia on the structure of the sugar moiety. Acylating efficiency of the 1-thioesters was additionally demonstrated by aminolysis of 2,3,4,6-tetra-O-acetyl-1-S-(N-tert-butyloxycarbonyl-L-tyrosyl)-1-thio-β-D- glucopyranose (3h) with peptidoglycan monomer (PGM, a disaccharide-pentapeptide) in N,N-dimethylformamide at room temperature to give the corresponding disaccharide-hexapeptide.
