Chemoenzymatic Synthesis and Facile Purification of Gangliosides

Yuanyuan Bai, Hai Yu, Xi Chen

Research output: Contribution to journalArticlepeer-review

Abstract

Gangliosides are biologically important sialic acid-containing glycolipids found commonly in human and other vertebrates. Isolation of pure gangliosides from cells or tissues is difficult, and chemical synthesis of gangliosides usually involves numerous steps with low synthetic yields. We report here a chemoenzymatic synthesis and purification protocol for two ganglioside cancer antigens, GM3 and GD3. One-pot multienzyme glycosylation reactions are used to sequentially prepare GM3 and GD3 sphingosines from chemically synthesized lactosyl sphingosine. A facile C18-cartridge purification procedure after each glycosylation reaction provides the desired pure glycosyl sphingosine product, which is readily acylated to form the target ganglioside.

Original languageEnglish (US)
Article numbere91
JournalCurrent Protocols
Volume1
Issue number3
DOIs
StatePublished - Mar 2021

Keywords

  • carbohydrate
  • chemoenzymatic synthesis
  • ganglioside
  • glycolipid
  • glycosphingolipid
  • sialic acid

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Neuroscience(all)
  • Immunology and Microbiology(all)
  • Health Informatics
  • Medical Laboratory Technology

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