Site-selective oxidation of vitamin B12 using 2-iodoxybenzoic acid

Susan Clardy-James, Jaime L. Bernstein, Deborah J. Kerwood, Robert P. Doyle

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Reaction of vitamin B12 (B12) with excess 2-iodoxybenzoic acid and 2-hydroxypyridine leads to selective oxidation of the 5'-hydroxyl group of the ribose tail of B12 in a 30% isolated yield. The acid derivative was purified in one step by HPLC chromatography and characterized by MALDI-TOF mass spectrometry, 1H NMR and 2D (HSQC and HMBC) NMR. The new carboxylic acid derivative is perfectly suited to make stable amide-based B12 bioconjugates.

Original languageEnglish (US)
Article numberST-2012-R0524-L
Pages (from-to)2363-2366
Number of pages4
JournalSynlett
Volume23
Issue number16
DOIs
StatePublished - Dec 1 2012

Keywords

  • 2-iodoxybenzoic acid
  • Carboxylic acids
  • Cobalamin
  • Oxidation
  • Vitamins

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Site-selective oxidation of vitamin B<sup>12</sup> using 2-iodoxybenzoic acid'. Together they form a unique fingerprint.

  • Cite this

    Clardy-James, S., Bernstein, J. L., Kerwood, D. J., & Doyle, R. P. (2012). Site-selective oxidation of vitamin B12 using 2-iodoxybenzoic acid. Synlett, 23(16), 2363-2366. [ST-2012-R0524-L]. https://doi.org/10.1055/S-0032-1317160