Acceptor-mediated regioselective enzyme catalyzed sialylation: chemoenzymatic synthesis of GAA-7 ganglioside glycan

Chem Commun (Camb). 2021 Apr 11;57(28):3468-3471. doi: 10.1039/d1cc00653c. Epub 2021 Mar 10.

Abstract

Herein, we applied PmST1 (a sialyltransferase) to achieve acceptor-mediated regioselective sialylation (AMRS) on the nonreducing end GalNH2 or GalAz (2-azido-2-deoxy galactose). Thus, C5 and C8-modified sialic acid was efficiently assembled on GalNH2 (or GalAz) to achieve the synthesis of the GAA-7 (one of the echinodermatous gangliosides with higher neuritogenic activity) glycan moiety.

MeSH terms

  • Biocatalysis
  • Carbohydrate Conformation
  • Gangliosides / biosynthesis*
  • Gangliosides / chemistry
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / metabolism*
  • Polysaccharides / biosynthesis*
  • Polysaccharides / chemistry
  • Sialyltransferases / metabolism*
  • Stereoisomerism

Substances

  • Gangliosides
  • Polysaccharides
  • ganglioside GAA-7
  • Sialyltransferases
  • N-Acetylneuraminic Acid