Literature DB >> 12816411

Formation of the dimethylbenzimidazole ligand of coenzyme B(12) under physiological conditions by a facile oxidative cascade.

Lori A Maggio-Hall1, Pieter C Dorrestein, Jorge C Escalante-Semerena, Tadhg P Begley.   

Abstract

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]

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Year:  2003        PMID： 12816411     DOI： 10.1021/ol034530m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Finding the final pieces of the vitamin B12 biosynthetic jigsaw.

Authors:  Martin J Warren
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-27       Impact factor: 11.205

2.  Pseudo-B12 joins the cofactor family.

Authors:  Michiko E Taga; Graham C Walker
Journal:  J Bacteriol       Date:  2007-12-14       Impact factor: 3.490

3.  Functional analysis of the nicotinate mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) enzyme, involved in the late steps of coenzyme B12 biosynthesis in Salmonella enterica.

Authors:  Kathy R Claas; J R Parrish; L A Maggio-Hall; J C Escalante-Semerena
Journal:  J Bacteriol       Date:  2010-01       Impact factor: 3.490

Review 4.  The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems.

Authors:  Chia-I Lin; Reid M McCarty; Hung-Wen Liu
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-14       Impact factor: 15.336

5.  BluB cannibalizes flavin to form the lower ligand of vitamin B12.

Authors:  Michiko E Taga; Nicholas A Larsen; Annaleise R Howard-Jones; Christopher T Walsh; Graham C Walker
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

6.  Single-enzyme conversion of FMNH2 to 5,6-dimethylbenzimidazole, the lower ligand of B12.

Authors:  Michael J Gray; Jorge C Escalante-Semerena
Journal:  Proc Natl Acad Sci U S A       Date:  2007-02-14       Impact factor: 11.205

7.  Active site residues critical for flavin binding and 5,6-dimethylbenzimidazole biosynthesis in the flavin destructase enzyme BluB.

Authors:  Ta-Yi Yu; Kenny C Mok; Kristopher J Kennedy; Julien Valton; Karen S Anderson; Graham C Walker; Michiko E Taga
Journal:  Protein Sci       Date:  2012-04-23       Impact factor: 6.725

8.  One pathway can incorporate either adenine or dimethylbenzimidazole as an alpha-axial ligand of B12 cofactors in Salmonella enterica.

Authors:  Peter J Anderson; Jozsef Lango; Colleen Carkeet; Audrey Britten; Bernhard Kräutler; Bruce D Hammock; John R Roth
Journal:  J Bacteriol       Date:  2007-11-02       Impact factor: 3.490

9.  Sinorhizobium meliloti bluB is necessary for production of 5,6-dimethylbenzimidazole, the lower ligand of B12.

Authors:  Gordon R O Campbell; Michiko E Taga; Kavita Mistry; Javier Lloret; Peter J Anderson; John R Roth; Graham C Walker
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-01       Impact factor: 11.205

10.  A Remarkable Oxidative Cascade That Replaces the Riboflavin C8 Methyl with an Amino Group during Roseoflavin Biosynthesis.

Authors:  Isita Jhulki; Prem K Chanani; Sameh H Abdelwahed; Tadhg P Begley
Journal:  J Am Chem Soc       Date:  2016-06-29       Impact factor: 15.419
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