Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors.
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.
Murruzzu
Caterina
C
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.
Alonso
Mònica
M
Canales
Angeles
A
Jiménez-Barbero
Jesus
J
Riera
Antoni
A
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002247:Carbon Isotopes; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation
D002247:Carbon Isotopes; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases