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

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

Izvornik
Croatica chemica acta (0011-1643) 69 (1996), 4; 1329-1337

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
aminolyses ; glycosyl ; N-acylamino acids

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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