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 journalArticle

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 languageEnglish (US)
Pages (from-to)10444-10447
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number33
DOIs
StatePublished - Aug 3 2015
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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