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

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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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 - 2012

Fingerprint

Vitamin B 12
Nuclear magnetic resonance
Derivatives
Oxidation
Ribose
Carboxylic Acids
Chromatography
Amides
Hydroxyl Radical
Mass spectrometry
Acids
2-iodoxybenzoic acid
2-hydroxypyridine

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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

Site-selective oxidation of vitamin B12 using 2-iodoxybenzoic acid. / Clardy-James, Susan; Bernstein, Jaime L.; Kerwood, Deborah J.; Doyle, Robert Patrick.

In: Synlett, Vol. 23, No. 16, ST-2012-R0524-L, 2012, p. 2363-2366.

Research output: Contribution to journalArticle

Clardy-James, S, Bernstein, JL, Kerwood, DJ & Doyle, RP 2012, 'Site-selective oxidation of vitamin B12 using 2-iodoxybenzoic acid', Synlett, vol. 23, no. 16, ST-2012-R0524-L, pp. 2363-2366. https://doi.org/10.1055/S-0032-1317160
Clardy-James S, Bernstein JL, Kerwood DJ, Doyle RP. Site-selective oxidation of vitamin B12 using 2-iodoxybenzoic acid. Synlett. 2012;23(16):2363-2366. ST-2012-R0524-L. https://doi.org/10.1055/S-0032-1317160
Clardy-James, Susan ; Bernstein, Jaime L. ; Kerwood, Deborah J. ; Doyle, Robert Patrick. / Site-selective oxidation of vitamin B12 using 2-iodoxybenzoic acid. In: Synlett. 2012 ; Vol. 23, No. 16. pp. 2363-2366.
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