Journal
TETRAHEDRON-ASYMMETRY
Volume 20, Issue 6-8, Pages 733-740Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2009.03.021
Keywords
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Funding
- EU Marie Curie Early Stage Training (EST) [MEST-CT-020575]
- Marie Curie Host Fellowships for the Transfer of Knowledge (ToK) [MTKD-CT-2006-042776]
- Hellenic General Secretariat for Research and Technology (GSRT)
- Ministry of Development
- EMBL-Hamburg outstation under FP6 'Structuring the European Research Area Programme' [RII3/CT/2004/5060008]
- SRS Daresbury Laboratory [IHPP HPRI-CT-1999-00012]
- Hungarian Scientific Research Fund [OTKA 61336, 68578]
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Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished beta-D-Glc(p)-NHCO-R derivatives as well as 1-(beta-D-Glc(p))-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. (C) 2009 Elsevier Ltd. All rights reserved.
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