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

Angad P. Mehta; Sameh H. Abdelwahed; Michael K. Fenwick; Amrita B. Hazra; Michiko E. Taga; Yang Zhang; Steven E. Ealick; Tadhg P. Begley

doi:10.1021/jacs.5b03576

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

Angad P. Mehta, Sameh H. Abdelwahed, Michael K. Fenwick, Amrita B. Hazra, Michiko E. Taga, Yang Zhang, Steven E. Ealick, Tadhg P. Begley

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	10444-10447
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	33
DOIs	https://doi.org/10.1021/jacs.5b03576
State	Published - Aug 3 2015
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Online availability

10.1021/jacs.5b03576

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Cite this

Mehta, A. P., Abdelwahed, S. H., Fenwick, M. K., Hazra, A. B., Taga, M. E., Zhang, Y., Ealick, S. E., & Begley, T. P. (2015). Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B₁₂ Biosynthesis. Journal of the American Chemical Society, 137(33), 10444-10447. https://doi.org/10.1021/jacs.5b03576

Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B₁₂ Biosynthesis. / Mehta, Angad P.; Abdelwahed, Sameh H.; Fenwick, Michael K. et al.
In: Journal of the American Chemical Society, Vol. 137, No. 33, 03.08.2015, p. 10444-10447.

Research output: Contribution to journal › Article › peer-review

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