C-Glycosidic UDP-GlcNAc Analogues as Inhibitors of UDP-GlcNAc 2-Epimerase

C-Glycosidic UDP-GlcNAc Analogues as Inhibitors of UDP-GlcNAc 2-Epimerase

The first step in the biosynthesis of neuraminic acid, the “epimerisation” of UDP‐GlcNAc to ManNAc, is catalyzed by UDP‐GlcNAc 2‐epimerase. In this paper we report the synthesis of the C‐glycosidic UDP‐GlcNAc analogues 1−5 as substrate‐based inhibitors of this enzyme. The focus is on the optimal dis...

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Veröffentlicht in:European journal of organic chemistry 2004-08, Vol.2004 (15), p.3304-3312
Hauptverfasser: Stolz, Florian, Blume, Astrid, Hinderlich, Stephan, Reutter, Werner, Schmidt, Richard R.
Format: Artikel
Sprache:eng
Schlagworte:
Biosynthesis
C-Glycoside
Carbohydrates
Inhibitors
Neuraminic acid
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Zusammenfassung:The first step in the biosynthesis of neuraminic acid, the “epimerisation” of UDP‐GlcNAc to ManNAc, is catalyzed by UDP‐GlcNAc 2‐epimerase. In this paper we report the synthesis of the C‐glycosidic UDP‐GlcNAc analogues 1−5 as substrate‐based inhibitors of this enzyme. The focus is on the optimal distance and geometry of the connection between the sugar and the UDP‐moiety, which are both important for recognition by UDP‐GlcNAc 2‐epimerase. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400197