Enzymatic Cascade Reactions in Biosynthesis

Angewandte Chemie
Christopher T Walsh, Bradley S Moore

Abstract

Enzyme-mediated cascade reactions are widespread in biosynthesis. To facilitate comparison with the mechanistic categorizations of cascade reactions by synthetic chemists and delineate the common underlying chemistry, we discuss four types of enzymatic cascade reactions: those involving nucleophilic, electrophilic, pericyclic, and radical reactions. Two subtypes of enzymes that generate radical cascades exist at opposite ends of the oxygen abundance spectrum. Iron-based enzymes use O2 to generate high valent iron-oxo species to homolyze unactivated C-H bonds in substrates to initiate skeletal rearrangements. At anaerobic end, enzymes reversibly cleave S-adenosylmethionine (SAM) to generate the 5'-deoxyadenosyl radical as a powerful oxidant to initiate C-H bond homolysis in bound substrates. The latter enzymes are termed radical SAM enzymes. We categorize the former as "thwarted oxygenases".

References

Apr 13, 1979·Science·J H CardellinaR E Moore
Aug 25, 1971·Journal of the American Chemical Society·W S JohnsonB E McCarry
Aug 15, 1995·Proceedings of the National Academy of Sciences of the United States of America·T SchweckeJ B Lester
Jan 3, 1995·Proceedings of the National Academy of Sciences of the United States of America·W Boland
Sep 20, 1997·Science·K U WendtG E Schulz
Sep 2, 1998·Nature·K ValegårdI Andersson
Dec 23, 1999·Current Opinion in Structural Biology·C J Schofield, Z Zhang
Jun 26, 2003·Journal of the American Chemical Society·Armen ZakarianRobert A Holton
Oct 19, 2004·Annual Review of Microbiology·Robert Finking, Mohamed A Marahiel
Oct 27, 2004·Proceedings of the National Academy of Sciences of the United States of America·Longkuan XiangBradley S Moore
Dec 4, 2004·Applied Microbiology and Biotechnology·Bettina Tudzynski
Apr 14, 2005·Journal of the American Chemical Society·Matthew W B Pfeiffer, Andrew J Phillips
Sep 17, 2005·Proceedings of the National Academy of Sciences of the United States of America·Bryan W LeporeDagmar Ringe
Jan 18, 2006·The Journal of Organic Chemistry·Kathlyn A Parker, Demosthenes Fokas
Apr 25, 2006·Chemistry & Biology·Andrew R GallimoreJonathan B Spencer
Nov 1, 2006·Angewandte Chemie·K C NicolaouPaul G Bulger
Jun 5, 2007·Accounts of Chemical Research·Carsten KrebsJ Martin Bollinger
Jul 4, 2007·Proceedings of the National Academy of Sciences of the United States of America·Masatomo MakinoShingo Nagano
Aug 21, 2007·Nature Chemical Biology·Qian ChengBradley S Moore
Aug 21, 2007·Journal of the American Chemical Society·Annaleise R Howard-Jones, Christopher T Walsh
Aug 21, 2007·Journal of the American Chemical Society·Silvia LodeiroSeiichi P T Matsuda
Sep 20, 2008·Science·Tomoshige HiratsukaTohru Dairi
Jan 30, 2009·Natural Product Reports·Andrew R Gallimore
Feb 14, 2009·Journal of Natural Products·John A KalaitzisBradley S Moore
Feb 20, 2009·Chembiochem : a European Journal of Chemical Biology·Naoki KatoHiroyuki Osada
Apr 14, 2009·Methods in Enzymology·Tiangang LiuZixin Deng
Jul 2, 2009·The Journal of Biological Chemistry·Andreas GesellToni M Kutchan
Jul 10, 2009·Nature·Paul A Wender, Benjamin L Miller
Jul 30, 2009·The Journal of Organic Chemistry·Sandy Desrat, Pierre van de Weghe
Oct 23, 2009·Chemical Society Reviews·K C Nicolaou, Jason S Chen
Feb 4, 2010·Journal of the American Chemical Society·Christopher T Walsh, Michael A Fischbach
May 19, 2010·Marine Drugs·Ralf KellmannKjetill S Jakobsen

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Citations

Nov 7, 2019·The FEBS Journal·David P Fewer, Mikko Metsä-Ketelä
Feb 13, 2020·Angewandte Chemie·Cangsong Liao, Florian P Seebeck
Feb 23, 2020·Chemistry : a European Journal·Mark A MaskeriKarl A Scheidt
Aug 25, 2020·Chembiochem : a European Journal of Chemical Biology·Daniel H ScharfChristian Hertweck
Oct 29, 2020·Chemical Society Reviews·Jiajie ChenJianlin Shi
Dec 23, 2020·Nature Chemistry·Danny Q Thach, Thomas J Maimone
Nov 19, 2020·Plants·Dmitriy N ShurpikIvan I Stoikov
Nov 24, 2020·Chemical Society Reviews·Yubo JiangEdward A Anderson
Mar 3, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Xuebin MaJingcheng Hao
Jan 23, 2021·Angewandte Chemie·Zhiyong SunChangzhu Wu
Apr 25, 2021·Advanced Materials·Weiqing XuChengzhou Zhu
Apr 29, 2021·Chemical Society Reviews·Cooper S JamiesonJohn M Billingsley
Apr 20, 2021·Frontiers in Cell and Developmental Biology·Pedro VizánSergi Aranda
Mar 7, 2021·Journal of Industrial Microbiology & Biotechnology·Yuxuan YeTodd K Hyster
May 13, 2021·Journal of Colloid and Interface Science·Jiarui XiaJunbai Li
May 25, 2021·Journal of the American Chemical Society·Yidong LiuKarl Anker Jørgensen
Jun 12, 2021·Journal of the American Chemical Society·Haigen FuTodd K Hyster
Jun 1, 2021·Chemistry : a European Journal·Mohammed Anif PashaDhevalapally B Ramachary
Feb 9, 2019·Accounts of Chemical Research·Alexandria Deliz LiangThomas R Ward
Jun 10, 2021·Chemistry : a European Journal·Weijin WangHans Renata
Aug 26, 2021·Journal of the American Chemical Society·Yun Bin HanRen Xiang Tan
Dec 19, 2019·The Journal of Organic Chemistry·Aaron J DayJonathan H George
Nov 17, 2020·Journal of the American Chemical Society·Yike ZouK N Houk
Oct 23, 2021·Chemistry : a European Journal·Guguloth ThirupathiDhevalapally B Ramachary

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