Intermolecular Aminolyses of 1-Thioglycosyl Esters of N-Acylamino Acids

Fully acetylated 1-thioglycopyranosyl esters of AT-acylaxnino acids (1-3), comprising different 1-thio sugars, undergo aminolysis with glycine methyl ester in dichloromethane at 40° to form the corresponding IV-acyldipeptide methyl esters. The relative reactivity of the C-l thioester bond towards am...

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Published inCroatica Chemica Acta Vol. 69; no. 4; p. 1329
Main Authors Ljevaković, Đurđica, Tomić, Srđanka, Tomašić, Jelka, Horvat, Jaroslav
Format Paper
LanguageEnglish
Published Hrvatsko kemijsko društvo 02.12.1996
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Summary:Fully acetylated 1-thioglycopyranosyl esters of AT-acylaxnino acids (1-3), comprising different 1-thio sugars, undergo aminolysis with glycine methyl ester in dichloromethane at 40° to form the corresponding IV-acyldipeptide methyl esters. The relative reactivity of the C-l 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- 0-aeetyl-l-S-(Af-fert-butyloxycmbonyl-L-tyrosyl)-l-thio-p-D-glucopyranose (3h) with peptidoglycan monomer (PGM, a disaccharide-pentapep- tide) in iV,)V-dimethylformamide at room temperature to give the corresponding disaccharide-hexapeptide.
Bibliography:135972
ISSN:0011-1643
1334-417X