Rational improvement of the synthesis of 1-deazariboflavin. Issue 11 (18th March 2015)

• Record Type: Journal Article
• Authors: Wood, Andrew C.; Knight, David W.; Richter, Gerald
• Is Part Of: Tetrahedron. Volume 71:Issue 11(2015)
• Page Start: 1679
• Page End: 1683
• Publication Date: 2015-03-18
• Subjects: Riboflavin -- 1-Deazariboflavin -- Flavoprotein -- Phototropin -- 5, 6-Dimethylbenzimidazole -- Synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.01.053
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: