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

Đurđica Ljevaković ; Institute of Immunology, Rockefellerova 10, 10000 Zagreb, Croatia
Srđanka Tomić ; Department of Chemistry, Faculty of Science, University of Zagreb, 10000 Zagreb, Croatia
Jelka Tomašić ; Institute of Immunology, Rockefellerova 10, 10000 Zagreb, Croatia
Jaroslav Horvat ; Department of Organic Chemistry and Biochemistry, Ruder Bošković Institute, 10000 Zagreb, Croatia


Puni tekst: engleski pdf 13.384 Kb

str. 1329-1337

preuzimanja: 289

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Sažetak

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.

Ključne riječi

Hrčak ID:

135972

URI

https://hrcak.srce.hr/135972

Posjeta: 490 *