English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  A diastereoselective P450-catalyzed epoxidation reaction: Anti versus syn reactivity

Ilie, A., Lonsdale, R., Agudo Torres, R., & Reetz, M. T. (2015). A diastereoselective P450-catalyzed epoxidation reaction: Anti versus syn reactivity. Tetrahedron Letters, 56(23), 3435-3437. doi:10.1016/j.tetlet.2015.03.076.

Item is

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Ilie, Adriana1, 2, Author              
Lonsdale, Richard1, 2, Author              
Agudo Torres, Rubén1, 2, Author              
Reetz, Manfred T.1, 2, Author              
Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
2Philipps-Universität Marburg, Fachbereich Chemie, ou_persistent22              

Content

show
hide
Free keywords: Biocatalysis; P450 monooxygenase; Olefin epoxidation; Diastereoselectivity; Oxidation
 Abstract: The achiral cyclohexene derivative dimethyl cis-1,2,3,6-tetrahydrophthalate has been subjected to oxidation catalyzed by cytochrome P450 monooxygenase P450-BM3, leading to diastereoselective epoxidation rather than oxidative hydroxylation. This reaction occurs with 94% diastereoselectivity in favor of the anti-epoxide, in contrast to m-CPBA which delivers unselectively a 70: 30 mixture of anti/syn diastereomers. The experimental results are nicely explained on a molecular level by docking experiments and molecular dynamics computations.The achiral cyclohexene derivative dimethyl cis-1,2,3,6-tetrahydrophthalate has been subjected to oxidation catalyzed by cytochrome P450 monooxygenase P450-BM3, leading to diastereoselective epoxidation rather than oxidative hydroxylation. This reaction occurs with 94% diastereoselectivity in favor of the anti-epoxide, in contrast to m-CPBA which delivers unselectively a 70: 30 mixture of anti/syn diastereomers. The experimental results are nicely explained on a molecular level by docking experiments and molecular dynamics computations.

Details

show
hide
Language(s): eng - English
 Dates: 2015-03-102014-12-042015-03-182015-03-212015-06-03
 Publication Status: Published in print
 Pages: 3
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.tetlet.2015.03.076
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Tetrahedron Letters
  Other : Tetrahedron Lett.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: -
Pages: - Volume / Issue: 56 (23) Sequence Number: - Start / End Page: 3435 - 3437 Identifier: ISSN: 0040-4039
CoNE: https://pure.mpg.de/cone/journals/resource/954925448772