Literature DB >> 16441088

A reassignment of (-)-mycothiazole and the isolation of a related diol.

Rachel N Sonnenschein1, Tyler A Johnson, Karen Tenney, Frederick A Valeriote, Phillip Crews.   

Abstract

A reinvestigation of the thiazole constituents from Cacospongia mycofijiensis, collected in Vanuatu, yielded known mycothiazole (3) plus a new derivative, mycothiazole-4,19-diol (6). The E stereochemistry at Delta14,15 of 3 has been revised to Z and the structural features of 6 are elucidated. These compounds, which presumably arise by the action of a polyketide-nonribosomal peptide synthetase (PKS/NRPS) hybrid, possess cytotoxic properties that need further exploration.

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Year:  2006        PMID： 16441088      PMCID： PMC2031212          DOI： 10.1021/np0503597

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  17 in total

1.  Discovery and development of anticancer agents from plants.

Authors:  Fred Valeriote; Charles K Grieshaber; Joseph Media; Halina Pietraszkewicz; Joseph Hoffmann; Meide Pan; Steve McLaughlin
Journal:  J Exp Ther Oncol       Date:  2002 Jul-Aug

2.  Melithiazol biosynthesis: further insights into myxobacterial PKS/NRPS systems and evidence for a new subclass of methyl transferases.

Authors:  Stefan Weinig; Hans-Jürgen Hecht; Taifo Mahmud; Rolf Müller
Journal:  Chem Biol       Date:  2003-10

3.  Molecular mechanisms underlying nonribosomal peptide synthesis: approaches to new antibiotics.

Authors:  Stephan A Sieber; Mohamed A Marahiel
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

4.  Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells.

Authors:  I Spector; N R Shochet; Y Kashman; A Groweiss
Journal:  Science       Date:  1983-02-04       Impact factor: 47.728

5.  Asymmetric total synthesis of (-)-mycothiazole.

Authors:  H Sugiyama; F Yokokawa; T Shioiri
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

6.  Total synthesis of (+/-)-mycothiazole and formal enantioselective approach.

Authors:  Alexandre Le Flohic; Christophe Meyer; Janine Cossy
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

7.  Latrunculins--novel marine macrolides that disrupt microfilament organization and affect cell growth: I. Comparison with cytochalasin D.

Authors:  I Spector; N R Shochet; D Blasberger; Y Kashman
Journal:  Cell Motil Cytoskeleton       Date:  1989

8.  Laulimalide and paclitaxel: a comparison of their effects on tubulin assembly and their synergistic action when present simultaneously.

Authors:  Eric J Gapud; Ruoli Bai; Arun K Ghosh; Ernest Hamel
Journal:  Mol Pharmacol       Date:  2004-07       Impact factor: 4.436

9.  A new dimension to the biosynthetic products isolated from the sponge Negombata magnifica.

Authors:  Boaz Vilozny; Taro Amagata; Susan L Mooberry; Phillip Crews
Journal:  J Nat Prod       Date:  2004-06       Impact factor: 4.050

10.  Microtubule-stabilizing agents based on designed laulimalide analogues.

Authors:  Susan L Mooberry; Deborah A Randall-Hlubek; Rachel M Leal; Sayee G Hegde; Robert D Hubbard; Lei Zhang; Paul A Wender
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-25       Impact factor: 11.205
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  17 in total

Review 1.  Highlights of marine invertebrate-derived biosynthetic products: their biomedical potential and possible production by microbial associants.

Authors:  Ocky K Radjasa; Yvette M Vaske; Gabriel Navarro; Hélène C Vervoort; Karen Tenney; Roger G Linington; Phillip Crews
Journal:  Bioorg Med Chem       Date:  2011-07-26       Impact factor: 3.641

2.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       Impact factor: 15.419

Review 3.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

4.  Reinvestigation of Mycothiazole Reveals the Penta-2,4-dien-1-ol Residue Imparts Picomolar Potency and 8S Configuration.

Authors:  Tyler A Johnson; Joseph D Morris; David A Coppage; Colon V Cook; Lauren N Persi; Marcos A Ogarrio; Taylor C Garcia; Nicole L McIntosh; Erin P McCauley; Joseph Media; Mani Maheshwari; Frederick A Valeriote; Jiajiu Shaw; Phillip Crews
Journal:  ACS Med Chem Lett       Date:  2020-01-02       Impact factor: 4.345

Review 5.  Bioactive Compounds from Marine Heterobranchs.

Authors:  Conxita Avila; Carlos Angulo-Preckler
Journal:  Mar Drugs       Date:  2020-12-21       Impact factor: 5.118

6.  Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.

Authors:  Tyler A Johnson; Johann Sohn; Wayne D Inman; Samarkand A Estee; Steven T Loveridge; Helene C Vervoort; Karen Tenney; Junke Liu; Kenny Kean-Hooi Ang; Joseline Ratnam; Walter M Bray; Nadine C Gassner; Young Y Shen; R Scott Lokey; James H McKerrow; Kyria Boundy-Mills; Arif Nukanto; Atit Kanti; Heddy Julistiono; Leonardus B S Kardono; Leonard F Bjeldanes; Phillip Crews
Journal:  J Nat Prod       Date:  2011-11-30       Impact factor: 4.050

7.  The aignopsanes, a new class of sesquiterpenes from selected chemotypes of the sponge Cacospongia mycofijiensis.

Authors:  Tyler A Johnson; Taro Amagata; Koneni V Sashidhara; Allen G Oliver; Karen Tenney; Teatulohi Matainaho; Kenny Kean-Hooi Ang; James H McKerrow; Phillip Crews
Journal:  Org Lett       Date:  2009-05-07       Impact factor: 6.005

Review 8.  A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

Authors:  Koneni V Sashidhara; Kimberly N White; Phillip Crews
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

9.  Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.

Authors:  Taro Amagata; Tyler A Johnson; Robert H Cichewicz; Karen Tenney; Susan L Mooberry; Joseph Media; Matthew Edelstein; Frederick A Valeriote; Phillip Crews
Journal:  J Med Chem       Date:  2008-11-27       Impact factor: 7.446

10.  Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.

Authors:  Tyler A Johnson; Karen Tenney; Robert H Cichewicz; Brandon I Morinaka; Kimberly N White; Taro Amagata; Balanehru Subramanian; Joseph Media; Susan L Mooberry; Frederick A Valeriote; Phillip Crews
Journal:  J Med Chem       Date:  2007-07-10       Impact factor: 7.446
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