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Literature DB >> 21796227

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

Timothy J McAfoos¹, Shengying Li, Sachiko Tsukamoto, David H Sherman, Robert M Williams.

Abstract

Notoamide S has been suggested to be the final common precursor between two different Aspergillus sp. fungal strains before diverging to form enantiomerically opposite natural products (+)- and (-)-stephacidin A and (+)- and (-)-notoamide B. The synthesis of notoamide S comes from the coupling of N-Fmoc proline with a 6-hydroxy-7-prenyl-2-reverse prenyl tryptophan derivative that was synthesized via a late stage Claisen rearrangement from a 6-propargyl-2-reverse prenylated indole.

Entities: CellLine Chemical Species

Year: 2010 PMID： 21796227 PMCID： PMC3143024 DOI： 10.3987/COM-10-S(E)19

Source DB: PubMed Journal: Heterocycles ISSN： 0385-5414 Impact factor: 0.831

20 in total

Review 1. Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors: Emily M Stocking; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2003-07-14 Impact factor: 15.336

2. A concise total synthesis of the notoamides C and D.

Authors: Alan W Grubbs; Gerald D Artman; Sachiko Tsukamoto; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. A concise, biomimetic total synthesis of stephacidin A and notoamide B.

Authors: Thomas J Greshock; Alan W Grubbs; Sachiko Tsukamoto; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. 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

5. 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

6. Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides.

Authors: R M Banks; S E Blanchflower; J R Everett; B R Manger; C Reading
Journal: J Antibiot (Tokyo) Date: 1997-10 Impact factor: 2.649

Review 7. 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

8. Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G.

Authors: J M Liesch; C F Wichmann
Journal: J Antibiot (Tokyo) Date: 1990-11 Impact factor: 2.649

9. 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

10. Improved biomimetic total synthesis of D,L-stephacidin A.

Authors: Thomas J Greshock; Robert M Williams
Journal: Org Lett Date: 2007-09-14 Impact factor: 6.005

13 in total

1. Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.

Authors: Yousong Ding; Jeffrey R de Wet; James Cavalcoli; Shengying Li; Thomas J Greshock; Kenneth A Miller; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Sachiko Tsukamoto; Robert M Williams; David H Sherman
Journal: J Am Chem Soc Date: 2010-09-15 Impact factor: 15.419

Review 2. Enantiomeric natural products: occurrence and biogenesis.

Authors: Jennifer M Finefield; David H Sherman; Martin Kreitman; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2012-05-03 Impact factor: 15.336

3. 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

4. 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

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

Authors: Shengying Li; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Robert M Williams; David H Sherman
Journal: J Am Chem Soc Date: 2011-12-28 Impact factor: 15.419

Review 6. 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

7. 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