Format

Send to

Choose Destination
J Am Chem Soc. 2015 Aug 26;137(33):10444-7. doi: 10.1021/jacs.5b03576. Epub 2015 Aug 13.

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

Author information

1
Department of Chemistry, Texas A&M University , College Station, Texas 77843, United States.
2
Therapeutic Chemistry Department, National Research Centre , Dokki, Cairo, Egypt.
3
Department of Chemistry and Chemical Biology, Cornell University , 120 Baker Lab, Ithaca, New York 14853, United States.
4
Department of Plant and Microbial Biology, University of California , Berkeley, California 94720, United States.

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.

PMID:
26237670
PMCID:
PMC4753784
DOI:
10.1021/jacs.5b03576
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center