Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides

Hai Yu, Hongzhi Cao, Vinod Kumar Tiwari, Yanhong Li, Xi Chen

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.

Original languageEnglish (US)
Pages (from-to)5037-5040
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number17
DOIs
StatePublished - Sep 1 2011

Keywords

  • C8-modification
  • Chemoenzymatic synthesis
  • Sialic acid
  • Sialoside
  • Sialyltransferase

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

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