569343-11-9Relevant articles and documents
Formation of the dimethylbenzimidazole ligand of coenzyme B12 under physiological conditions by a facile oxidative cascade
Maggio-Hall, Lori A.,Dorrestein, Pieter C.,Escalante-Semerena, Jorge C.,Begley, Tadhg P.
, p. 2211 - 2213 (2003)
(Matrix presented) 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.
Rational improvement of the synthesis of 1-deazariboflavin
Wood, Andrew C.,Knight, David W.,Richter, Gerald
, p. 1679 - 1683 (2015/03/18)
The cofactor forms of riboflavin (FMN and FAD) play a crucial role in the mediation of both enzymatic processes and light perception by photo-sensitive proteins, and thus structural analogues of this chromophore are highly useful tools to assist in the elucidation of enzymatic mechanisms. 1-Deazariboflavin has been rarely utilised for this purpose, due in part to its previously difficult and inefficient synthesis. Recent examination has enabled a remarkable improvement in the overall synthetic yield from 11.0 to 61.3%, allowing reliable production of 1-deazariboflavin for use as a tool in enzymatic mechanistic determination.
Improved Chemical Syntheses of 1- and 5-Deazariboflavin
Carlson, Erin E.,Kiessling, Laura L.
, p. 2614 - 2617 (2007/10/03)
The cofactor flavin adenine dinucleotide (FAD) is required for the catalytic activity of a large class of enzymes known as flavoenzymes. Because flavin cofactors participate in catalysis via a number of different mechanisms, isoalloxazine analogues are valuable for mechanistic studies. We report improved chemical syntheses for the preparation of the two key analogues, 5-deazariboflavin and 1-deazariboflavin.
