Parallel chemoenzymatic synthesis of sialosides containing a C5-diversified sialic acid

Bioorg Med Chem Lett. 2009 Oct 15;19(20):5869-71. doi: 10.1016/j.bmcl.2009.08.078. Epub 2009 Aug 26.

Abstract

A convenient chemoenzymatic strategy for synthesizing sialosides containing a C5-diversified sialic acid was developed. The alpha2,3- and alpha2,6-linked sialosides containing a 5-azido neuraminic acid synthesized by a highly efficient one-pot three-enzyme approach were converted to C5''-amino sialosides, which were used as common intermediates for chemical parallel synthesis to quickly generate a series of sialosides containing various sialic acid forms.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • N-Acetylneuraminic Acid / chemistry*
  • N-Acylneuraminate Cytidylyltransferase / chemistry
  • N-Acylneuraminate Cytidylyltransferase / metabolism
  • Oxo-Acid-Lyases / chemistry
  • Oxo-Acid-Lyases / metabolism
  • Sialyltransferases / chemistry
  • Sialyltransferases / metabolism

Substances

  • Glycosides
  • Sialyltransferases
  • N-Acylneuraminate Cytidylyltransferase
  • Oxo-Acid-Lyases
  • N-acetylneuraminate lyase
  • N-Acetylneuraminic Acid