Literature DB >> 23249380

Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.

James D Sunderhaus1, Timothy J McAfoos, Jennifer M Finefield, Hikaru Kato, Shengying Li, Sachiko Tsukamoto, David H Sherman, Robert M Williams.   

Abstract

In an effort to further elucidate the biogenesis of the stephacidin and notoamide families of natural products, notoamide T has been identified as the likely precursor to stephacidin A. The total synthesis of notoamide T is described along with it is C-6-epimer, 6-epi-notoamide T. The chemical conversion of stephacidin A to notoamide T by reductive ring opening is described as well as the oxidative conversion of notoamide T to stephacidin A. Furthermore, [(13)C](2)-notoamide T was synthesized and provided to Aspergillus versicolor and Aspergillus sp. MF297-2, in which significant incorporation was observed in the advanced metabolite, notoamide B.

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Year:  2012        PMID： 23249380      PMCID： PMC3549551          DOI： 10.1021/ol302901p

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

1.  Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.

Authors:  Hikaru Kato; Takushi Yoshida; Takanori Tokue; Yuka Nojiri; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams; Sachiko Tsukamoto
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

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.  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

4.  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

Review 5.  Fungal origins of the bicyclo[2.2.2]diazaoctane ring system of prenylated indole alkaloids.

Authors:  Jennifer M Finefield; Jens C Frisvad; David H Sherman; Robert M Williams
Journal:  J Nat Prod       Date:  2012-04-15       Impact factor: 4.050

6.  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

Review 7.  Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

Authors:  Robert M Williams; Rhona J Cox
Journal:  Acc Chem Res       Date:  2003-02       Impact factor: 22.384

Review 8.  Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.

Authors:  Robert Michael Williams
Journal:  Chem Pharm Bull (Tokyo)       Date:  2002-06       Impact factor: 1.645

9.  Notoamide O, a structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hideharu Umaoka; Kohei Yoshikawa; Tsuyoshi Ikeda; Hiroshi Hirota
Journal:  J Nat Prod       Date:  2010-08-27       Impact factor: 4.050

10.  Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Tetsuro Kawabata; Hikaru Kato; Thomas J Greshock; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005
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  12 in total

1.  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

2.  Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners.

Authors:  Ken Mukai; Danilo Pereira de Sant'Ana; Yasuo Hirooka; Eduardo V Mercado-Marin; David E Stephens; Kevin G M Kou; Sven C Richter; Naomi Kelley; Richmond Sarpong
Journal:  Nat Chem       Date:  2017-09-18       Impact factor: 24.427

3.  Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts.

Authors:  Hikaru Kato; Aika Kai; Tetsuro Kawabata; James D Sunderhaus; Timothy J McAfoos; Jennifer M Finefield; Yukihiko Sugimoto; Robert M Williams; Sachiko Tsukamoto
Journal:  Bioorg Med Chem Lett       Date:  2017-10-09       Impact factor: 2.823

4.  Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.

Authors:  Hikaru Kato; Takashi Nakahara; Kayo Sugimoto; Kanae Matsuo; Ippei Kagiyama; Jens C Frisvad; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Org Lett       Date:  2015-01-23       Impact factor: 6.005

5.  Bioconversion of 6-epi-Notoamide T Produces Metabolites of Unprecedented Structures in a Marine-derived Aspergillus sp.

Authors:  Hikaru Kato; Takashi Nakahara; Michitaka Yamaguchi; Ippei Kagiyama; Jennifer M Finefield; James D Sunderhaus; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Tetrahedron Lett       Date:  2015-01-01       Impact factor: 2.415

6.  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

7.  Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.

Authors:  Chao Qi; Yuan Xiong; Vincent Eschenbrenner-Lux; Huan Cong; John A Porco
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

Review 8.  Enzyme evolution in fungal indole alkaloid biosynthesis.

Authors:  Amy E Fraley; David H Sherman
Journal:  FEBS J       Date:  2020-04       Impact factor: 5.542

Review 9.  Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.

Authors:  Kimberly R Klas; Hikaru Kato; Jens C Frisvad; Fengan Yu; Sean A Newmister; Amy E Fraley; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

Review 10.  Marine Indole Alkaloids.

Authors:  Natalie Netz; Till Opatz
Journal:  Mar Drugs       Date:  2015-08-06       Impact factor: 5.118
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