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

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Author

  • L Verotta
  • E Lovaglio
  • Olov Sterner
  • G Appendino
  • E Bombardelli

Summary, in 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.

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 (ACS)

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 1520-6904