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

Verotta, L; Lovaglio, E; Sterner, Olov LU ; Appendino, G and Bombardelli, E (2004) In Journal of Organic Chemistry 69(23). p.7869-7874
Abstract
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.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
69
issue
23
pages
7869 - 7874
publisher
The American Chemical Society
external identifiers
  • wos:000225024200012
  • scopus:8644221313
ISSN
1520-6904
DOI
10.1021/jo048857s
language
English
LU publication?
yes
id
e8223d35-83b1-4867-a287-9f994a2f0f99 (old id 141131)
date added to LUP
2007-07-10 14:56:31
date last changed
2017-11-05 03:35:08
@article{e8223d35-83b1-4867-a287-9f994a2f0f99,
  abstract     = {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.},
  author       = {Verotta, L and Lovaglio, E and Sterner, Olov and Appendino, G and Bombardelli, E},
  issn         = {1520-6904},
  language     = {eng},
  number       = {23},
  pages        = {7869--7874},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Modulation of chemoselectivity by protein additives. Remarkable effects in the oxidation of hyperforin},
  url          = {http://dx.doi.org/10.1021/jo048857s},
  volume       = {69},
  year         = {2004},
}