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- Title
Synthesis of Stable Dolichylphosphomannose Analogues.
- Authors
Anna Kulesza; Christian 4;G. Frank; Markus Aebi; Andrea Vasella
- Abstract
Four oleyl or dolichyl thiophosphate esters 16, 17, 21, and 22, analogues of Dol-P-Man possessing C(1)—S and/or P—S bonds, were synthesized as potential inhibitors of mannosyl transferases operating in the endoplasmic reticulum (ER). The -mannosyl derivatives were prepared by a Mitsunobu reaction of 2,3,4,6-tetra-O-acetyl-a-D-mannopyranose (1) with the thiophosphate 2 that provided O- and S-glycosides with good-to-excellent diastereoselectivity. A second route to -mannosyl derivatives is based on the phosphitylation of the -D-mannopyranosyl thiol 3 with the phosphoramidites 4a and 4b. Oxidation of the intermediate oleyl thiophosphite with t-BuOOH led to mono- and dithiophosphates. The thiophospholipids 16, 21, and 22 were inactive as inhibitors of the Man6(GlcNAc)2-PP-Dol glycolipid elongation.
- Subjects
THIOPHOSPHATES; ORGANIC compounds; ENZYMES; GLYCOSIDES
- Publication
Helvetica Chimica Acta, 2004, Vol 87, Issue 12, p3106
- ISSN
0018-019X
- Publication type
Article