Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids

Hongzhi Cao; Yanhong Li; Kam Lau; Saddam Muthana; Hai Yu; Jiansong Cheng; Harshal A. Chokhawala; Go Sugiarto; Lei Zhang; Xi Chen

doi:10.1039/B916305K

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Organic & Biomolecular Chemistry

Issue 24, 2009

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Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids

Hongzhi Cao , Yanhong Li , Kam Lau , Saddam Muthana , Hai Yu , Jiansong Cheng , Harshal A. Chokhawala , Go Sugiarto , Lei Zhang and Xi Chen

Org. Biomol. Chem., 2009, 7, 5137-5145

DOI: 10.1039/B916305K
Received 10 Aug 2009, Accepted 22 Sep 2009
First published on the web 26 Oct 2009

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para-Nitrophenol-tagged sialyl galactosides containing sialic acid derivatives in which the C5 hydroxyl group of sialic acids was systematically substituted with a hydrogen, a fluorine, a methoxyl or an azido group were successfully synthesized using an efficient chemoenzymatic approach. These compounds were used as valuable probes in high-throughput screening assays to study the importance of the C5 hydroxyl group of sialic acid in the recognition and the cleavage of sialoside substrates by bacterial sialidases.

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Organic & Biomolecular Chemistry

Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids

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