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Mechanistic Studies of the Radical S-Adenosyl-L-methionine Enzyme 4-Demethylwyosine Synthase Reveal the Site of Hydrogen Atom Abstraction.

Authors
  • Young, Anthony P
  • Bandarian, Vahe
Type
Published Article
Journal
Biochemistry
Publisher
American Chemical Society
Publication Date
Jun 16, 2015
Volume
54
Issue
23
Pages
3569–3572
Identifiers
DOI: 10.1021/acs.biochem.5b00476
PMID: 26052987
Source
Medline
License
Unknown

Abstract

TYW1 catalyzes the formation of 4-demethylwyosine via the condensation of N-methylguanosine (m¹G) with carbons 2 and 3 of pyruvate. In this study, labeled transfer ribonucleic acid (tRNA) and pyruvate were utilized to determine the site of hydrogen atom abstraction and regiochemistry of the pyruvate addition. tRNA containing a ²H-labeled m¹G methyl group was used to identify the methyl group of m¹G as the site of hydrogen atom abstraction by 5'-deoxyadenosyl radical. [2-¹³C₁-3,3,3-²H₃]Pyruvate was used to demonstrate retention of all the pyruvate protons, indicating that C2 of pyruvate forms the bridging carbon of the imidazoline ring and C3 the methyl.

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