Regio- and stereoselective intermolecular phenol coupling enzymes in secondary metabolite biosynthesis.

Natural Product Reports
Wolfgang Hüttel, Michael Müller

Abstract

Covering: 2005 to 2020Phenol coupling is a key reaction in the biosynthesis of important biopolymers such as lignin and melanin and of a plethora of biarylic secondary metabolites. The reaction usually leads to several different regioisomeric products due to the delocalization of a radical in the reaction intermediates. If axial chirality is involved, stereoisomeric products are obtained provided no external factor influences the selectivity. Hence, in non-enzymatic organic synthesis it is notoriously difficult to control the selectivity of the reaction, in particular if the coupling is intermolecular. From biosynthesis, it is known that especially fungi, plants, and bacteria produce biarylic compounds regio- and stereoselectively. Nonetheless, the involved enzymes long evaded discovery. First progress was made in the late 1990s; however, the breakthrough came only with the genomic era and, in particular, in the last few years the number of relevant publications has dramatically increased. The discoveries reviewed in this article reveal a remarkable diversity of enzymes that catalyze oxidative intermolecular phenol coupling, including various classes of laccases, cytochrome P450 enzymes, and heme peroxidases. Particularly in th...Continue Reading

References

Aug 30, 1975·Journal of the American Chemical Society·D L DreyerG D Daves
Feb 1, 1987·Chemical & Pharmaceutical Bulletin·K Koyama, S Natori
Mar 14, 1995·Proceedings of the National Academy of Sciences of the United States of America·P F Kraus, T M Kutchan
Jul 20, 2002·Phytochemistry·Alfred M Mayer, Richard C Staples
Jul 20, 2002·Phytochemistry·Daniel Arrieta-BaezManuel Jiménez-Estrada
Sep 11, 2003·Natural Product Reports·Richard D Firn, Clive G Jones
Aug 7, 2004·The Journal of Biological Chemistry·Julien ValtonVincent Nivière
Aug 24, 2005·Angewandte Chemie·Gerhard BringmannMatthias Breuning
Sep 16, 2005·Proceedings of the National Academy of Sciences of the United States of America·Pieter C DorresteinChristopher T Walsh
Jan 13, 2006·Phytochemistry·Chauncey R BenedictRobert D Stipanovic
Feb 23, 2007·Chembiochem : a European Journal of Chemical Biology·Wolfgang Hüttel, Michael Müller
Apr 28, 2007·Molecular Microbiology·Huiqin ChenKuang-Ren Chung
Jul 4, 2007·Angewandte Chemie·Silke E BodeMichael Müller
Feb 9, 2010·Applied and Environmental Microbiology·Yi-Ming ChiangBerl R Oakley
Mar 20, 2010·Journal of Microbiological Methods·Perng-Kuang ChangDeepak Bhatnagar
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Oct 27, 2010·Archives of Biochemistry and Biophysics·Max J CryleIlme Schlichting
Feb 8, 2011·The Journal of Biological Chemistry·Rasmus J N FrandsenHenriette Giese
Mar 26, 2011·Journal of the American Chemical Society·Ying L ZhangRen X Tan
Jul 20, 2011·Proceedings of the National Academy of Sciences of the United States of America·Zhiyang FengSean F Brady
Dec 29, 2011·Archives of Biochemistry and Biophysics·Bin ZhaoMichael R Waterman
Jan 10, 2012·Journal of the American Chemical Society·Zhiyang FengSean F Brady
Jul 18, 2012·Journal of the American Chemical Society·Kazuya YamanakaBradley S Moore
Aug 3, 2012·The Journal of Biological Chemistry·Kye-Won KimNorman G Lewis
Sep 5, 2012·Angewandte Chemie·Christian Gil GirolMichael Müller
Oct 31, 2012·Chemical Communications : Chem Comm·Adam G NewmanCraig A Townsend
Aug 31, 2013·Applied Microbiology and Biotechnology·Benjamin Pickel, Andreas Schaller
Jan 28, 2014·PloS One·Jérôme CollemarePierre J G M de Wit
Mar 29, 2014·Chembiochem : a European Journal of Chemical Biology·Takayoshi SaruwatariKenji Watanabe

❮ Previous
Next ❯

Related Concepts

Related Feeds

Bioinformatics in Biomedicine

Bioinformatics in biomedicine incorporates computer science, biology, chemistry, medicine, mathematics and statistics. Discover the latest research on bioinformatics in biomedicine here.