Literature DB >> 18844365

Premalbrancheamide: synthesis, isotopic labeling, biosynthetic incorporation, and detection in cultures of Malbranchea aurantiaca.

Yousong Ding1, Thomas J Greshock, Kenneth A Miller, David H Sherman, Robert M Williams.   

Abstract

An advanced metabolite, named premalbrancheamide, involved in the biosynthesis of malbrancheamide (1) and malbrancheamide B (2) has been synthesized in double (13)C-labeled form and was incorporated into the indole alkaloid 2 by Malbranchea aurantiaca. In addition, premalbrancheamide has been detected as a natural metabolite in cultures of M. aurantiaca. The biosynthetic implications of these experiments are discussed.

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Year:  2008        PMID： 18844365      PMCID： PMC2651399          DOI： 10.1021/ol8019633

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


  24 in total

1.  Asymmetric total synthesis of (-)-VM55599: establishment of the absolute stereochemistry and biogenetic implications.

Authors:  Juan F Sanz-Cervera; Robert M Williams
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

2.  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

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.  Reversal of P-glycoprotein mediated multidrug resistance in K562 cell line by a novel synthetic calmodulin inhibitor, E6.

Authors:  Hao-Jie Zhu; Jun-Sheng Wang; Qing-Long Guo; Yan Jiang; Guo-Qing Liu
Journal:  Biol Pharm Bull       Date:  2005-10       Impact factor: 2.233

5.  Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1h)-pyrazinones.

Authors:  S Jin; P Wessig; J Liebscher
Journal:  J Org Chem       Date:  2001-06-01       Impact factor: 4.354

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

7.  Synthesis and structure-activity relationships of novel pyrrolocarbazole lactam analogs as potent and cell-permeable inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1).

Authors:  Gregory J Wells; Ron Bihovsky; Robert L Hudkins; Mark A Ator; Jean Husten
Journal:  Bioorg Med Chem Lett       Date:  2005-12-15       Impact factor: 2.823

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.  Asymmetric aerobic oxidation of alpha-hydroxy acid derivatives by C4-symmetric, vanadate-centered, tetrakisvanadyl(V) clusters derived from N-salicylidene-alpha-aminocarboxylates.

Authors:  Chien-Tien Chen; Sampada Bettigeri; Shiue-Shien Weng; Vijay D Pawar; Ya-Hui Lin; Cheng-Yuan Liu; Way-Zen Lee
Journal:  J Org Chem       Date:  2007-10-04       Impact factor: 4.354

10.  Concise, Biomimetic Total Synthesis of d,l-Marcfortine C.

Authors:  Thomas J Greshock; Alan W Grubbs; Robert M Williams
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457
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  14 in total

1.  Function and Structure of MalA/MalA', Iterative Halogenases for Late-Stage C-H Functionalization of Indole Alkaloids.

Authors:  Amy E Fraley; Marc Garcia-Borràs; Ashootosh Tripathi; Dheeraj Khare; Eduardo V Mercado-Marin; Hong Tran; Qingyun Dan; Gabrielle P Webb; Katharine R Watts; Phillip Crews; Richmond Sarpong; Robert M Williams; Janet L Smith; K N Houk; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-08-21       Impact factor: 15.419

2.  Notoamide E: Biosynthetic incorporation into notoamides C and D in cultures of Aspergillus versicolor NRRL 35600.

Authors:  Jennifer M Finefield; Thomas J Greshock; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2011-04-20       Impact factor: 2.415

3.  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

4.  Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide.

Authors:  Jacob G Robins; Kyu J Kim; Alex J Chinn; John S Woo; Jonathan R Scheerer
Journal:  J Org Chem       Date:  2016-02-26       Impact factor: 4.354

5.  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

Review 6.  Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors:  Kenneth A Miller; Robert M Williams
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

Review 7.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

Review 8.  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

9.  Utilizing DART mass spectrometry to pinpoint halogenated metabolites from a marine invertebrate-derived fungus.

Authors:  Katharine R Watts; Steven T Loveridge; Karen Tenney; Joseph Media; Frederick A Valeriote; Phillip Crews
Journal:  J Org Chem       Date:  2011-06-29       Impact factor: 4.354

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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