Literature DB >> 26237670

Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B₁₂ Biosynthesis.

Angad P Mehta1, Sameh H Abdelwahed1,2, Michael K Fenwick3, Amrita B Hazra4, Michiko E Taga4, Yang Zhang3, Steven E Ealick3, Tadhg P Begley1.   

Abstract

Comparative genomics of the bacterial thiamin pyrimidine synthase (thiC) revealed a paralogue of thiC (bzaF) clustered with anaerobic vitamin B12 biosynthetic genes. Here we demonstrate that BzaF is a radical S-adenosylmethionine enzyme that catalyzes the remarkable conversion of aminoimidazole ribotide (AIR) to 5-hydroxybenzimidazole (5-HBI). We identify the origin of key product atoms and propose a reaction mechanism. These studies represent the first step in solving a long-standing problem in anaerobic vitamin B12 assembly and reveal an unanticipated intersection of thiamin and vitamin B12 biosynthesis.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 26237670      PMCID： PMC4753784          DOI： 10.1021/jacs.5b03576

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Basic local alignment search tool.

Authors:  S F Altschul; W Gish; W Miller; E W Myers; D J Lipman
Journal:  J Mol Biol       Date:  1990-10-05       Impact factor: 5.469

2.  Biosynthesis of vitamin B-12 in anaerobic bacteria. Experiments with Eubacterium limosum and D-erythrose 14C-labeled in different positions.

Authors:  J R Vogt; L Lamm-Kolonko; P Renz
Journal:  Eur J Biochem       Date:  1988-07-01

3.  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

4.  Biosynthesis of vitamin B-12 in anaerobic bacteria. Experiments with Eubacterium limosum on the origin of the amide groups of the corrin ring and of N-3 of the 5,6-dimethylbenzimidazole part.

Authors:  J R Vogt; P Renz
Journal:  Eur J Biochem       Date:  1988-02-01

Review 5.  Discovering nature's diverse pathways to vitamin B12: a 35-year odyssey.

Authors:  A Ian Scott
Journal:  J Org Chem       Date:  2003-04-04       Impact factor: 4.354

6.  Trichodiene synthase. Probing the role of the highly conserved aspartate-rich region by site-directed mutagenesis.

Authors:  D E Cane; Q Xue; B C Fitzsimons
Journal:  Biochemistry       Date:  1996-09-24       Impact factor: 3.162

7.  Precursor of carbon atom five and hydroxymethyl carbon atom of the pyrimidine moiety of thiamin in Escherichia coli.

Authors:  K Yamada; H Kumaoka
Journal:  J Nutr Sci Vitaminol (Tokyo)       Date:  1983-08       Impact factor: 2.000

8.  Biosynthesis of vitamin B12 in anaerobic bacteria. Transformation of 5-hydroxybenzimidazole and 5-hydroxy-6-methylbenzimidazole into 5,6-dimethylbenzimidazole in Eubacterium limosum.

Authors:  P Renz; B Endres; B Kurz; J Marquart
Journal:  Eur J Biochem       Date:  1993-11-01

9.  Biosynthesis of vitamin B12 in anaerobic bacteria. Experiments with Eubacterium limosum on the incorporation of D-[1-13C]erythrose and [13C]formate into the 5,6-dimethylbenzimidazole moiety.

Authors:  M Munder; J R Vogt; B Vogler; P Renz
Journal:  Eur J Biochem       Date:  1992-03-01

10.  Non-canonical active site architecture of the radical SAM thiamin pyrimidine synthase.

Authors:  Michael K Fenwick; Angad P Mehta; Yang Zhang; Sameh H Abdelwahed; Tadhg P Begley; Steven E Ealick
Journal:  Nat Commun       Date:  2015-03-27       Impact factor: 14.919
View more
  13 in total

1.  Crystal Structures of the Iron-Sulfur Cluster-Dependent Quinolinate Synthase in Complex with Dihydroxyacetone Phosphate, Iminoaspartate Analogues, and Quinolinate.

Authors:  Michael K Fenwick; Steven E Ealick
Journal:  Biochemistry       Date:  2016-07-22       Impact factor: 3.162

Review 2.  Decoding molecular interactions in microbial communities.

Authors:  Nicole A Abreu; Michiko E Taga
Journal:  FEMS Microbiol Rev       Date:  2016-07-13       Impact factor: 16.408

3.  Organometallic and radical intermediates reveal mechanism of diphthamide biosynthesis.

Authors:  Min Dong; Venkatesan Kathiresan; Michael K Fenwick; Andrew T Torelli; Yang Zhang; Jonathan D Caranto; Boris Dzikovski; Ajay Sharma; Kyle M Lancaster; Jack H Freed; Steven E Ealick; Brian M Hoffman; Hening Lin
Journal:  Science       Date:  2018-03-16       Impact factor: 47.728

4.  CobT and BzaC catalyze the regiospecific activation and methylation of the 5-hydroxybenzimidazole lower ligand in anaerobic cobamide biosynthesis.

Authors:  Yamini Mathur; Sheryl Sreyas; Prathamesh M Datar; Manjima B Sathian; Amrita B Hazra
Journal:  J Biol Chem       Date:  2020-06-05       Impact factor: 5.157

5.  Structural studies of viperin, an antiviral radical SAM enzyme.

Authors:  Michael K Fenwick; Yue Li; Peter Cresswell; Yorgo Modis; Steven E Ealick
Journal:  Proc Natl Acad Sci U S A       Date:  2017-06-12       Impact factor: 11.205

6.  Exchange of Vitamin B1 and Its Biosynthesis Intermediates Shapes the Composition of Synthetic Microbial Cocultures and Reveals Complexities of Nutrient Sharing.

Authors:  Rupali R M Sathe; Ryan W Paerl; Amrita B Hazra
Journal:  J Bacteriol       Date:  2022-03-31       Impact factor: 3.476

7.  Anaerobic biosynthesis of the lower ligand of vitamin B12.

Authors:  Amrita B Hazra; Andrew W Han; Angad P Mehta; Kenny C Mok; Vadim Osadchiy; Tadhg P Begley; Michiko E Taga
Journal:  Proc Natl Acad Sci U S A       Date:  2015-08-05       Impact factor: 11.205

Review 8.  C-C bond forming radical SAM enzymes involved in the construction of carbon skeletons of cofactors and natural products.

Authors:  Kenichi Yokoyama; Edward A Lilla
Journal:  Nat Prod Rep       Date:  2018-07-18       Impact factor: 13.423

9.  An Aminoimidazole Radical Intermediate in the Anaerobic Biosynthesis of the 5,6-Dimethylbenzimidazole Ligand to Vitamin B12.

Authors:  Derek M Gagnon; Troy A Stich; Angad P Mehta; Sameh H Abdelwahed; Tadhg P Begley; R David Britt
Journal:  J Am Chem Soc       Date:  2018-09-27       Impact factor: 15.419

10.  Structural Basis of the Substrate Selectivity of Viperin.

Authors:  Michael K Fenwick; Dan Su; Min Dong; Hening Lin; Steven E Ealick
Journal:  Biochemistry       Date:  2020-01-16       Impact factor: 3.162
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.