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Intermolecular aminolyses of 1-thioglycosyl esters of N-acylamino acids (CROSBI ID 88772)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Ljevaković, Đurđica ; Tomić, Srđanka ; Tomašić, Jelka ; Horvat, Jaroslav Intermolecular aminolyses of 1-thioglycosyl esters of N-acylamino acids // Croatica chemica acta, 69 (1996), 4; 1329-1337

Podaci o odgovornosti

Ljevaković, Đurđica ; Tomić, Srđanka ; Tomašić, Jelka ; Horvat, Jaroslav

engleski

Intermolecular aminolyses of 1-thioglycosyl esters of N-acylamino acids

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.

aminolyses ; glycosyl ; N-acylamino acids

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Podaci o izdanju

69 (4)

1996.

1329-1337

objavljeno

0011-1643

1334-417X

Povezanost rada

Kemija

Indeksiranost