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Mechanism of S-Adenosyl-l-methionine C-Methylation by Cobalamin-dependent Radical S-Adenosyl-l-methionine Methylase in 1-Amino-2-methylcyclopropanecarboxylic Acid Biosynthesis.
Kudo, Fumitaka; Minato, Atsushi; Sato, Shusuke; Nagano, Nayuta; Maruyama, Chitose; Hamano, Yoshimitsu; Hashimoto, Junko; Kozone, Ikuko; Shin-Ya, Kazuo; Eguchi, Tadashi.
Afiliação
  • Kudo F; Department of Chemistry, Tokyo Institute of Technology, O-okayama, Tokyo 152-8551, Japan.
  • Minato A; Department of Chemistry, Tokyo Institute of Technology, O-okayama, Tokyo 152-8551, Japan.
  • Sato S; Department of Chemistry, Tokyo Institute of Technology, O-okayama, Tokyo 152-8551, Japan.
  • Nagano N; Department of Chemistry, Tokyo Institute of Technology, O-okayama, Tokyo 152-8551, Japan.
  • Maruyama C; Department of Bioscience, Fukui Prefectural University, 4-1-1 Yoshida-Gun, Fukui 910-1195, Japan.
  • Hamano Y; Department of Bioscience, Fukui Prefectural University, 4-1-1 Yoshida-Gun, Fukui 910-1195, Japan.
  • Hashimoto J; Japan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
  • Kozone I; Japan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
  • Shin-Ya K; National Institute of Advanced Industrial Science and Technology, 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
  • Eguchi T; Department of Chemistry, Tokyo Institute of Technology, O-okayama, Tokyo 152-8551, Japan.
Org Lett ; 24(49): 8975-8979, 2022 12 16.
Article em En | MEDLINE | ID: mdl-36458844
ABSTRACT
The radical S-adenosyl-l-methionine (SAM) methylase Orf29 catalyzes the C-methylation of SAM in the biosynthesis of 1-amino-2-methylcyclopropanecarboxylic acid. Here, we determined that the methylation product is (4″R)-4″-methyl-SAM. Furthermore, we found that the 5'-deoxyadenosyl radical generated by Orf29 abstracts the pro-R hydrogen atom from the C-4″ position of SAM to generate the radical intermediate, which reacts with methylcobalamin to give (4″R)-4″-methyl-SAM. Consequently, the Orf29-catalyzed C-methylation was confirmed to proceed with retention of configuration.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: S-Adenosilmetionina / Metionina Idioma: En Revista: Org Lett Ano de publicação: 2022 Tipo de documento: Article
Texto completo
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XML
PubMed Links
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: S-Adenosilmetionina / Metionina Idioma: En Revista: Org Lett Ano de publicação: 2022 Tipo de documento: Article