A novel direct glycosylation approach for the synthesis of dimers of N- acetylneuraminic acid

Alexei V. Demchenko, Geert Jan Boons*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The dimer Neu5Aca(2←8)Neu5Ac is an important constituent of tumor- associated antigens. Until now, direct glycosylation methods for the synthesis of this disaccharide have failed and only laborious indirect methods have been applied. Here, we describe a novel and highly reactive 2- methylthioneuraminyl donor bearing a di-N-acetyl (N-acetylacetamido) functionality at C-5. Surprisingly, the additional N-acetyl moiety of this glycosyl donor dramatically increases its reactivity and gives excellent yields in glycosylations with the 8-hydroxyl of N-acetylneuraminic acid derivatives. Minimizing the steric hindrance around the 8-position of a Neu5Ac glycosyl acceptor resulted in higher yields of glycosylation products, but in this case the α-anomeric selectivity was compromised.

Original languageEnglish
Pages (from-to)1278-1283
Number of pages6
JournalChemistry - A European Journal
Volume5
Issue number4
DOIs
Publication statusPublished - 1 Jan 1999
Externally publishedYes

Keywords

  • Carbohydrates
  • Glycosylations
  • Neuraminic acids
  • Oligosaccharides
  • Synthetic methods

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