Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc |
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Authors: | Marek Baráth Miroslav Koóš Igor Tvaroška Ján Hirsch |
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Institution: | 1.Institute of Chemistry, Center for Glycomics,Slovak Academy of Sciences,Bratislava,Slovakia;2.Department of Chemistry, Faculty of Natural Sciences,Constantine The Philosopher University,Nitra,Slovakia |
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Abstract: | Based on rational design of the transition state analog inhibitors of glycosyltransferases, four model glycomimetics of this type, viz. benzyl 2-thio-α-dfructofuranoside 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. |
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