Synthesis of ceramidated GLA-60 derivatives

Carbohydr Res. 2002 Sep 3;337(15):1343-9. doi: 10.1016/s0008-6215(02)00179-9.

Abstract

Ceramidated GLA-60 derivatives 11 and 11' were synthesized from 1 via glycosidation of ceramide derivative 12 as a glycosyl acceptor with GLA-60 derivative 5 as a glycosyl donor, and successive conversion. Compound 11' showed only weak LPS-antagonistic activity without showing any LPS-agonistic activity.

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / chemistry
  • Ceramides / chemistry*
  • Lipid A / analogs & derivatives*
  • Lipid A / chemical synthesis*
  • Lipid A / chemistry
  • Molecular Structure
  • Spectrophotometry, Infrared

Substances

  • Adjuvants, Immunologic
  • Ceramides
  • Lipid A
  • GLA 60