Total synthesis of alkaloids using both chemical and biochemical methods.

Natural Product Reports
Ryo TanifujiHideaki Oikawa

Abstract

Covering: 2000 to 2019Rapid access to genomic data has facilitated the identification of the biosynthetic enzyme genes of alkaloid natural products and elucidation of their biosynthetic pathways. Enzymes for the rapid construction of molecular scaffolds and versatile modifications during the late-stage biosynthesis of complex molecular skeletons constitute unique features of biosynthetic machineries. For example, enzymes involved in an alkaloid biosynthesis. In this review, we discuss three types of useful enzymes and enzymatic reactions that have been found in the biosynthetic studies of several alkaloids, and discuss their applications for the total synthesis of natural alkaloids and their derivatives. The selected examples include a single non-ribosomal peptide synthetase SfmC that catalyzes key Pictet-Spengler reactions, which construct a characteristic tetrahydroisoquinoline skeleton in antitumor antibiotics such as saframycin, prenylation-oxidative modification enzymes involved in the biosynthesis of fungal tremorgenic mycotoxins such as penitrem as well as versatile Diels-Alderases recently discovered in the biosynthesis of plant monoterpene indole alkaloids of iboga and aspidosperma type.

References

Nov 1, 1977·The Journal of Antibiotics·T AraiA Kubo
Jul 1, 1985·Antimicrobial Agents and Chemotherapy·T AraiY Mikami
May 9, 2002·Chemical Reviews·Jack D Scott, Robert M Williams
Mar 6, 2003·Chemistry & Biology·Junko NakazawaHiroyuki Osada
Jul 3, 2003·Journal of the American Chemical Society·Amos B SmithWilliam H Moser
Sep 25, 2004·Journal of Natural Products·Sheo B SinghJan S Tkacz
May 19, 2006·Organic Letters·Dylan B EnglandMichael A Kerr
Jul 29, 2006·Natural Product Reports·Sarah E O'Connor, Justin J Maresh
Feb 12, 2008·Mycological Research·Sanjay SaikiaBarry Scott
Feb 3, 2009·Applied and Environmental Microbiology·Carolyn A YoungBarry Scott
Feb 26, 2009·Natural Product Reports·Carmen Cuevas, Andrés Francesch
May 11, 2010·Nature Chemical Biology·Kento KoketsuHideaki Oikawa
Jul 15, 2011·Nature·Spencer B JonesDavid W C MacMillan
Mar 14, 2012·Current Opinion in Chemical Biology·Kento KoketsuHideaki Oikawa
May 5, 2012·Angewandte Chemie·Jennifer M FinefieldRobert M Williams
Nov 9, 2012·Angewandte Chemie·Masaru EnomotoShigefumi Kuwahara
Jan 15, 2013·Journal of the American Chemical Society·Koichi TagamiHideaki Oikawa
Mar 8, 2013·Natural Product Reports·Minoru IshikuraSatoshi Hibino
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Oct 12, 2013·Chemical Communications : Chem Comm·Jonathan William Medley, Mohammad Movassaghi
Dec 18, 2013·Natural Product Reports·Christian A KuttruffPhil S Baran
Dec 19, 2013·Nature Chemistry·Haruki MizoguchiHiroki Oguri
Jul 9, 2014·Journal of the American Chemical Society·Joel W Beatty, Corey R J Stephenson
Aug 5, 2014·Chembiochem : a European Journal of Chemical Biology·Koichi TagamiHideaki Oikawa
Sep 4, 2014·Bioscience, Biotechnology, and Biochemistry·Takaaki TeranishiShigefumi Kuwahara
Feb 13, 2015·Proceedings of the National Academy of Sciences of the United States of America·Stephanie BrownSarah E O'Connor
May 1, 2015·Organic & Biomolecular Chemistry·Haruki MizoguchiHiroki Oguri
Jun 2, 2015·Journal of the American Chemical Society·Yike ZouAmos B Smith
Jul 8, 2015·Natural Product Reports·Minoru IshikuraSatoshi Hibino
Mar 29, 2016·The Journal of Organic Chemistry·Masashi YokoyaNaoki Saito
May 11, 2016·Organic Letters·Gaoyuan ZhaoXuegong She
Jul 14, 2016·Organic & Biomolecular Chemistry·Junhao JiaXiaochuan Chen
Aug 12, 2016·Journal of the American Chemical Society·Kolby L White, Mohammad Movassaghi

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Citations

Nov 13, 2020·Proceedings of the Japan Academy. Series B, Physical and Biological Sciences·Hideaki Oikawa
Apr 29, 2021·Organic & Biomolecular Chemistry·Hiroaki Ohno, Shinsuke Inuki
Sep 3, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Li ZhaiRan Hong

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