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Synthesis of phosphonate analogues of CMP-Neu5Ac determination of α(2–6)-sialyltransferase inhibition

✍ Scribed by Bernd Müller; Thomas J. Martin; Christoph Schaub; Richard R. Schmidt

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
206 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of sialyl phosphites with TMSOTf as catalyst affords a-and ~-sialyl phosphonates. This phospshite/phosphonate-exchange reaction was employed for the synthesis of sialylphosphonate dialkyl esters 5aa-5Ca and 5a13-Sg[3. Monodemethylation of 5ca and 5c13, linkage to 5'-O-unprotected cytidine derivative 7, and then deprotection furnished the phosphonate analogue 213 of CMP-Neu5Ac and the corresponding a-isomer 2a, respectively. Their structures could be assigned and inhibition of a(2-6)-sialyltransferase was determined.

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## Abstract Sialyloligosaccharides are synthesised by various glycosyltransferases and sugar nucleotides. All of these nucleotides are diphosphate compounds except for cytidine‐5′‐monophosphosialic acid (CMP‐Neu5Ac). To obtain an insight into why cytidine‐5′‐diphosphosialic acid (CDP‐Neu5Ac) has no