Synthesis of sulfone-based nucleotide isosteres: identification of CMP-sialic acid synthetase inhibitors

Jessica H. Wong; Urvashi Sahni; Yanhong Li; Xi Chen; Jacquelyn Gervay-Hague

doi:10.1039/B819155G

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Organic & Biomolecular Chemistry

Issue 1, 2009

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Synthesis of sulfone-based nucleotide isosteres: identification of CMP-sialic acid synthetase inhibitors

Jessica H. Wong , Urvashi Sahni , Yanhong Li , Xi Chen and Jacquelyn Gervay-Hague

Org. Biomol. Chem., 2009, 7, 27-29

DOI: 10.1039/B819155G
Received 28 Oct 2008, Accepted 29 Oct 2008
First published on the web 17 Nov 2008

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Abstract
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A modular replacement approach to the synthesis of sulfo-nucleotide analogs prepared from condensation of nucleoside aldehydes with bis phosphonate Horner-Wadsworth-Emmons reagents is disclosed. These analogs were shown to be inhibitors of Neisseria meningitidis CSS (NmCSS), which is a key enzyme in the biosynthesis of the capsular polysaccharides required for bacterial infection.

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Experimental details of compound syntheses and NmCSSsubstrate and inhibition assays; NMR, HRMS, HPLC and CEspectra
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Jessica H. Wong
Urvashi Sahni
Yanhong Li
Xi Chen
Jacquelyn Gervay-Hague

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Organic & Biomolecular Chemistry

Synthesis of sulfone-based nucleotide isosteres: identification of CMP-sialic acid synthetase inhibitors

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