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Modulation of chemoselectivity by protein additives. Remarkable effects in the oxidation of hyperforin

Author:
  • L Verotta
  • E Lovaglio
  • Olov Sterner
  • G Appendino
  • E Bombardelli
Publishing year: 2004
Language: English
Pages: 7869-7874
Publication/Series: Journal of Organic Chemistry
Volume: 69
Issue: 23
Document type: Journal article
Publisher: The American Chemical Society

Abstract english

Protein additives have a dramatic effect on the H2O2 oxidation of hyperforin, either protecting the enolized phloroglucinol core from oxidation (human albumin) or promoting (HRP and ovalbumin) reaction pathways derived from the intermediacy of the enollactone 4, a minor component of the oxidation mixture in the absence of protein additives. To rationalize the exquisite specificity of several steps and their mechanistic oddity, an organocatalytic effect is postulated. The use of protein additives allows a straightforward and multigram preparation of the enollactone 6, an interesting multifunctionalized scaffold for bioactivity induction and/or modulation.

Keywords

  • Organic Chemistry

Other

Published
  • ISSN: 1520-6904
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

Dean

Faculty of Science

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Professor

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