Methyl transfer from a hydrophobic vitamin B12 derivative to arsenic trioxide

Koichiro Nakamura, Yoshio Hisaeda, Ling Pan, Hiroshi Yamauchi

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Abstract

The methylation reaction of arsenic trioxide conducted at 37 °C and pH 7.0 for 24 h using hydrophobic methylated vitamin B12, (methyl) (aquo) heptamethylcobyrinate perchlorate, CH3B12 ester, as a methyl donor in the presence of reduced glutathione (GSH) yielded monomethylarsonous acid (MMA), dimethylarsinic acid (DMA), and trimethylarsine oxide (TMAO) as products with a methylation rate over 95%. In contrast, when methylcobalamin (CH3B12) was used as the methyl donor, only MMA and DMA were produced and the methylation rate dropped to around 20%. Reductive demethylation of a methyl-corrinoid coordination complex mediated by GSH is suggested as a mechanism of methyl transfer to arsenic trioxide. The differences observed for different corrinoid coordination complexes with respect to the reactivity of methyl transfer to arsenic is ascribable to differences inherent in the base-on (CH3B12) and base-off (CH3B12 ester) natures of the compounds.

Original languageEnglish
Pages (from-to)916-921
Number of pages6
JournalJournal of Organometallic Chemistry
Volume694
Issue number6
DOIs
Publication statusPublished - Mar 15 2009

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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