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Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine.

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Author

  • Nafizal Hossain
  • Amparo Zapata
  • Mikael Wilstermann
  • Ulf Nilsson
  • Göran Magnusson

Summary, in English

The novel sialyl donor methyl (ethyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-2-thio-3-thiophenyl-D-erythro-beta-L-gluco-non-2-ulopyranosid)onate was used for glycosylation of a lactosyl acceptor to give the GM3-trisaccharide derivative in 83% yield. Introduction of an azido group at C-9" of the GM3-trisaccharide derivative, transformation into a glycosyl acceptor, and sialylation with the above mentioned novel sialyl donor gave a GD3-trisaccharide in 50% yield. Reduction of the azido group gave the corresponding amine, which underwent spontaneous lactamization to the GD3-[1"'-9"]-lactam in an overall yield of 86%. Removal of protecting groups of over five steps, followed by per-O-acetylation gave an acetylated GD3-[1"'-9"]-lactam TMSEt glycoside in 27% overall yield. The acetylated GD3-[1"'-9"]-lactam TMSEt glycoside is suitable for glycosylation of linker-arms and the resulting linker-glycosides are planned to be coupled to carrier proteins, thus providing immunogens for trial vaccinations against malignant melanoma.

Publishing year

2002

Language

English

Pages

569-580

Publication/Series

Carbohydrate Research

Volume

337

Issue

7

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry

Keywords

  • Melanoma
  • Antigen
  • GD3
  • GD3-lactam
  • Glycosylation

Status

Published

ISBN/ISSN/Other

  • ISSN: 1873-426X