Article

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

Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
Organic & Biomolecular Chemistry (impact factor: 3.7). 05/2012; 10(30):6112-20. DOI:10.1039/c2ob25335f pp.6112-20
Source: PubMed

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 Neu5Gc9N(3)2en and Neu5AcN(3)9N(3)2en are selective inhibitors against V. cholerae sialidase and human NEU2, respectively.

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Keywords

2-deoxy-2,3-dehydro-N-acetylneuraminic acid
 
bacterial
 
human cytosolic sialidase NEU2
 
human NEU2
 
human sialidases
 
influenza virus neuraminidases
 
neuraminidases catalyze
 
sialidase crystal structural analysis
 
sialidase substrate specificity studies
 
successes
 
synthesizing selective inhibitors
 
terminal sialic acid residues
 
various bacterial sialidases