engleski

Intermolecular aminolysis of 1-thioglycosyl esters of N-acylaminoacids

Fully acetylated 1-thioglycopyranosyl esters of N- acylamino acids, comprising different 1-thio sugars, undergo aminolysis with glycine methyl ester in dichloromethane at 40 degrees Celsius to form the dorrespnding 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-thio-esters was additionally demonstrated by aminolysis of 2, 3, 4, 6-tetra-O-acetyl-1-S-(N-tert-butyloxycarbonyl- L-tyrosyl)-1-thio-beta-D-glucopyranose (3h) with peptidoglycan monomer (PGM, a disaccharide- pentapeptide) in N, N-dimethylformamide at room temperature to give the corresponding disaccharide-hexapeptide.

peptidoglycan monomer ; thio-esters ; monosaccharides ; aminolysis

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