Literature DB >> 22188465

Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.

Shengying Li1, Jennifer M Finefield, James D Sunderhaus, Timothy J McAfoos, Robert M Williams, David H Sherman.   

Abstract

Notoamides produced by Aspergillus spp. bearing the bicyclo[2.2.2]diazaoctane core structure with unusual structural diversity represent a compelling system to understand the biosynthesis of fungal prenylated indole alkaloids. Herein, we report the in vitro characterization of NotB, which catalyzes the indole 2,3-oxidation of notoamide E (13), leading to notoamides C (11) and D (12) through an apparent pinacol-like rearrangement. This unique enzymatic reaction with high substrate specificity, together with the information derived from precursor incorporation experiments using [(13)C](2)-[(15)N](2) quadruply labeled notoamide S (10), demonstrates 10 as a pivotal branching point in notoamide biosynthesis.
© 2011 American Chemical Society

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Year:  2011        PMID： 22188465      PMCID： PMC3275806          DOI： 10.1021/ja2093212

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  25 in total

1.  New paraherquamide antibiotics with anthelmintic activity.

Authors:  S E Blanchflower; R M Banks; J R Everett; B R Manger; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1991-05       Impact factor: 2.649

2.  Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hikaru Kato; Masayuki Samizo; Yuka Nojiri; Hiroyuki Onuki; Hiroshi Hirota; Tomihisa Ohta
Journal:  J Nat Prod       Date:  2008-12       Impact factor: 4.050

3.  Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.

Authors:  James D Sunderhaus; David H Sherman; Robert M Williams
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

4.  Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors:  Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 5.  Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis.

Authors:  Shu-Ming Li
Journal:  Nat Prod Rep       Date:  2009-11-19       Impact factor: 13.423

6.  Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.

Authors:  Jennifer M Finefield; Robert M Williams
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

7.  STUDIES ON THE BIOSYNTHESIS OF THE STEPHACIDINS AND NOTOAMIDES. TOTAL SYNTHESIS OF NOTOAMIDE S.

Authors:  Timothy J McAfoos; Shengying Li; Sachiko Tsukamoto; David H Sherman; Robert M Williams
Journal:  Heterocycles       Date:  2010-12-31       Impact factor: 0.831

8.  Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.

Authors:  Jennifer M Finefield; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  J Org Chem       Date:  2011-06-28       Impact factor: 4.354

9.  Enzymatic processing of fumiquinazoline F: a tandem oxidative-acylation strategy for the generation of multicyclic scaffolds in fungal indole alkaloid biosynthesis.

Authors:  Brian D Ames; Xinyu Liu; Christopher T Walsh
Journal:  Biochemistry       Date:  2010-09-08       Impact factor: 3.162

10.  Complexity generation in fungal peptidyl alkaloid biosynthesis: oxidation of fumiquinazoline A to the heptacyclic hemiaminal fumiquinazoline C by the flavoenzyme Af12070 from Aspergillus fumigatus.

Authors:  Brian D Ames; Stuart W Haynes; Xue Gao; Bradley S Evans; Neil L Kelleher; Yi Tang; Christopher T Walsh
Journal:  Biochemistry       Date:  2011-09-19       Impact factor: 3.162
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  26 in total

1.  Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

Authors:  Sunkyu Han; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-10-31       Impact factor: 4.354

2.  Isolation of amoenamide A and five antipodal prenylated alkaloids from Aspergillus amoenus NRRL 35600.

Authors:  Kayo Sugimoto; Yusaku Sadahiro; Ippei Kagiyama; Hikaru Kato; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Tetrahedron Lett       Date:  2017-05-18       Impact factor: 2.415

3.  Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk.

Authors:  Yuta Tsunematsu; Noriyasu Ishikawa; Daigo Wakana; Yukihiro Goda; Hiroshi Noguchi; Hisao Moriya; Kinya Hotta; Kenji Watanabe
Journal:  Nat Chem Biol       Date:  2013-10-13       Impact factor: 15.040

Review 4.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

Review 5.  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 6.  Biosynthesis of fungal indole alkaloids.

Authors:  Wei Xu; Diego J Gavia; Yi Tang
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

Review 7.  Flavoenzymes: versatile catalysts in biosynthetic pathways.

Authors:  Christopher T Walsh; Timothy A Wencewicz
Journal:  Nat Prod Rep       Date:  2013-01       Impact factor: 13.423

8.  Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.

Authors:  Amy E Fraley; Hong T Tran; Samantha P Kelly; Sean A Newmister; Ashootosh Tripathi; Hikaru Kato; Sachiko Tsukamoto; Lei Du; Shengying Li; Robert M Williams; David H Sherman
Journal:  Chembiochem       Date:  2020-05-14       Impact factor: 3.164

9.  Palladium-catalyzed synthesis of N-tert-prenylindoles.

Authors:  Kirsten F Johnson; Ryan Van Zeeland; Levi M Stanley
Journal:  Org Lett       Date:  2013-05-28       Impact factor: 6.005

10.  Comparative analysis of the biosynthetic systems for fungal bicyclo[2.2.2]diazaoctane indole alkaloids: the (+)/(-)-notoamide, paraherquamide and malbrancheamide pathways.

Authors:  Shengying Li; Krithika Anand; Hong Tran; Fengan Yu; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Sachiko Tsukamoto; Robert M Williams; David H Sherman
Journal:  Medchemcomm       Date:  2012-08       Impact factor: 3.597
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