Literature DB >> 29711662

Biosynthesis of Psoralen: Mechanism of a Cytochrome P450 Catalyzed Oxidative Bond Cleavage.

Volker Stanjek1, Martin Miksch1, Patricia Lueer2, Ulrich Matern2, Wilhelm Boland1.   

Abstract

In contrast to the stepwise oxidative dealkylation of steroids [Eq. (1)], (+)-marmesin (1) is directly converted by the psoralen synthase (a cytochrome P450) into the phototoxic furanocoumarin psoralen (2) and acetone. The dealkylation proceeds as a syn elimination. © 1999 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  biosynthesis; Cytochrome; Eliminations; Furocoumarins; Porphyrinoids

Year:  1999        PMID： 29711662     DOI： 10.1002/(SICI)1521-3773(19990201)38:3<400::AID-ANIE400>3.0.CO;2-K

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  Molecular probes of the mechanism of cytochrome P450. Oxygen traps a substrate radical intermediate.

Authors:  Harriet L R Cooper; John T Groves
Journal:  Arch Biochem Biophys       Date:  2010-11-12       Impact factor: 4.013

Review 2.  Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.

Authors:  F Peter Guengerich; Francis K Yoshimoto
Journal:  Chem Rev       Date:  2018-06-22       Impact factor: 60.622

Review 3.  Hydrocarbon hydroxylation by cytochrome P450 enzymes.

Authors:  Paul R Ortiz de Montellano
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

4.  Evolution of substrate recognition sites (SRSs) in cytochromes P450 from Apiaceae exemplified by the CYP71AJ subfamily.

Authors:  Bjørn Dueholm; Célia Krieger; Damian Drew; Alexandre Olry; Tsunashi Kamo; Olivier Taboureau; Corinna Weitzel; Frédéric Bourgaud; Alain Hehn; Henrik Toft Simonsen
Journal:  BMC Evol Biol       Date:  2015-06-26       Impact factor: 3.260

5.  A terpene synthase-cytochrome P450 cluster in Dictyostelium discoideum produces a novel trisnorsesquiterpene.

Authors:  Xinlu Chen; Katrin Luck; Patrick Rabe; Christopher Qd Dinh; Gad Shaulsky; David R Nelson; Jonathan Gershenzon; Jeroen S Dickschat; Tobias G Köllner; Feng Chen
Journal:  Elife       Date:  2019-05-07       Impact factor: 8.140

Review 6.  Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites.

Authors:  Víctor Coca-Ruíz; Ivonne Suárez; Josefina Aleu; Isidro G Collado
Journal:  Plants (Basel)       Date:  2022-03-14
  6 in total

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