Modulation of chemoselectivity by protein additives. Remarkable effects in the oxidation of hyperforin
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/141131
- author
- Verotta, L ; Lovaglio, E ; Sterner, Olov LU ; Appendino, G and Bombardelli, E
- organization
- publishing date
- 2004
- 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 (ACS)
- external identifiers
-
- wos:000225024200012
- scopus:8644221313
- ISSN
- 1520-6904
- DOI
- 10.1021/jo048857s
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- e8223d35-83b1-4867-a287-9f994a2f0f99 (old id 141131)
- date added to LUP
- 2016-04-01 11:55:26
- date last changed
- 2022-01-26 20:16:07
@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 (ACS)}}, 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}}, doi = {{10.1021/jo048857s}}, volume = {{69}}, year = {{2004}}, }