ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc

Marek Baráth, Miroslav Koóš, Igor Tvaroška, and Ján Hirsch

Institute of Chemistry, Center for Glycomics, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38 Bratislava

E-mail: marek.barath@savba.sk

Abstract: Based on rational design of the transition state analog inhibitors of glycosyltransferases, four model glycomimetics of this type, viz. benzyl 2-thio-α-D-fructofuranoside 1-diethylphosphate (XIa), its β-anomer (XIb), and their ethyl 2-thio analogs - α-anomer (XIIa) and β-anomer (XIIb), were synthesized. In addition, fourteen precursors arising during the synthesis of the desired final model compounds (XI and XII), partially or fully acetylated benzyl and/or ethyl 2-thiofructofuranoside 1-diethyl phosphates, were isolated and characterized with the aim to prepare complete series of glycomimetics, representing donor UDP-GlcNAc designated for biological assays on human GnT’s, viz. GnT-I, Core2GnT, and GnT-V.

Keywords: glycosyltransferases – inhibitors – fructofuranoside – mimetics – acetyl migration – GlcNAc- UDP

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0017

Chemical Papers 69 (2) 339–347 (2015)