Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors.

Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Biomedical Research (IRB) and Departament de Química Orgànica, Universitat de Barcelona, Parc Científic de Barcelona c/Josep Samitier, 1-5, 08028 Barcelona, Spain.

The synthesis of (4,5,6-13C)-deoxymannojirimycin is described. The route employed is based on Sharpless asymmetric epoxidation of (1,2,3-13C)(E)-2,4-pentadien-1-ol and uses ring-closing metathesis as a key step. The labeled compound may be easily used for protein-binding experiments using NMR spectroscopic methods.

PMID: 17511974 [PubMed - indexed for MEDLINE]