Total synthesis of a hexaosyl ceramide glycolipid acting as a receptor for macrophage migration inhibition-factor
✍ Scribed by Peter Zimmermann; Ulrike Greilich; Richard R. Schmidt
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 207 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A synthesis of the glycosphingolipid 1 constituting a macrophage receptor for MIF is described. It is based on trichloroacetirnidate glycosyl donors and on the azidosphingosine glycosylation method. Regioselective O-glycosylation of a partially O-protected acceptor and direct transformation of the sphingosine azido group into a fatty acyl amido function were successfully applied in the execution of the synthesis.
Sugar residues play an important role as structure specific epitopes in biological recognition 2-4. They also participate in the recognition process of macrophages 5,6. Thus, studies concerning the interaction of the MIF (migration inhibition factor) with rat macrophages exhibited that MIF activity was specifically blocked by glycosphingolipid 16) which was detected as a major constituent of the glycosphingolipids in rat peritoneal macrophages and structurally elucidated 7,8,