Synthesis of selective inhibitors against V. cholerae sialidase and human cytosolic sialidase NEU2

Zahra Khedri, Yanhong Li, Hongzhi Cao, Jingyao Qu, Hai Yu, Musleh M. Muthana, Xi Chen

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14 Scopus citations

Abstract

Sialidases or neuraminidases catalyze the hydrolysis of terminal sialic acid residues from sialyl oligosaccharides and glycoconjugates. Despite successes in developing potent inhibitors specifically against influenza virus neuraminidases, the progress in designing and synthesizing selective inhibitors against bacterial and human sialidases has been slow. Guided by sialidase substrate specificity studies and sialidase crystal structural analysis, a number of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (DANA or Neu5Ac2en) analogues with modifications at C9 or at both C5 and C9 were synthesized. Inhibition studies of various bacterial sialidases and human cytosolic sialidase NEU2 revealed that Neu5Gc9N32en and Neu5AcN39N 32en are selective inhibitors against V. cholerae sialidase and human NEU2, respectively.

Original languageEnglish (US)
Pages (from-to)6112-6120
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number30
DOIs
StatePublished - Aug 14 2012

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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