Formation of the dimethylbenzimidazole ligand of coenzyme B(12) under physiological conditions by a facile oxidative cascade.
Dimethylbezimidazole, the axial ligand of vitamin B(12), is synthesized from riboflavin by a two-electron oxidation, a retro-aldol condensation, and a second two-electron oxidation. This oxidative cascade readily takes place nonenzymatically under physiological conditions. [reaction: see text]
Maggio-Hall
Lori A
LA
Department of Bacteriology, University of Wisconsin, 1710 University Avenue, Madison, WI 53726-4087, USA.
Dorrestein
Pieter C
PC
Escalante-Semerena
Jorge C
JC
Begley
Tadhg P
TP
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003038:Cobamides / Q000378:metabolism*; D008024:Ligands; D010084:Oxidation-Reduction; D012256:Riboflavin / Q000737:chemistry
D001562:Benzimidazoles; D003038:Cobamides; D008024:Ligands; C015158:5,6-dimethylbenzimidazole; D012256:Riboflavin