Literature DB >> 18808124

A new total synthesis of patellamide A.

Pablo García-Reynaga1, Michael S VanNieuwenhze.   

Abstract

Patellamide A was efficiently synthesized from thiazole 2 via two complementary heterocyclization approaches to form the thiazole and oxazoline rings.

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Year:  2008        PMID： 18808124      PMCID： PMC4096709          DOI： 10.1021/ol801895y

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


  11 in total

1.  Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids.

Authors:  Shu-Li You; Songpon Deechongkit; Jeffery W Kelly
Journal:  Org Lett       Date:  2004-07-22       Impact factor: 6.005

2.  Patellamide A and C biosynthesis by a microcin-like pathway in Prochloron didemni, the cyanobacterial symbiont of Lissoclinum patella.

Authors:  Eric W Schmidt; James T Nelson; David A Rasko; Sebastian Sudek; Jonathan A Eisen; Margo G Haygood; Jacques Ravel
Journal:  Proc Natl Acad Sci U S A       Date:  2005-05-09       Impact factor: 11.205

Review 3.  Marine metabolites: metal binding and metal complexes of azole-based cyclic peptides of marine origin.

Authors:  Anna Bertram; Gerald Pattenden
Journal:  Nat Prod Rep       Date:  2007-01-16       Impact factor: 13.423

4.  Natural combinatorial peptide libraries in cyanobacterial symbionts of marine ascidians.

Authors:  Mohamed S Donia; Brian J Hathaway; Sebastian Sudek; Margo G Haygood; M J Rosovitz; Jacques Ravel; Eric W Schmidt
Journal:  Nat Chem Biol       Date:  2006-11-05       Impact factor: 15.040

5.  A marine natural product, patellamide D, reverses multidrug resistance in a human leukemic cell line.

Authors:  A B Williams; R S Jacobs
Journal:  Cancer Lett       Date:  1993-07-30       Impact factor: 8.679

6.  A biomimetic synthesis of thiazolines using hexaphenyloxodiphosphonium trifluoromethanesulfonate.

Authors:  Shu-Li You; Hossein Razavi; Jeffery W Kelly
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-03       Impact factor: 15.336

7.  Highly efficient biomimetic total synthesis and structural verification of bistratamides E and J from Lissoclinum bistratum.

Authors:  Shu-Li You; Jeffery W Kelly
Journal:  Chemistry       Date:  2004-01-05       Impact factor: 5.236

8.  Total synthesis of dendroamide a: oxazole and thiazole construction using an oxodiphosphonium salt.

Authors:  Shu-Li You; Jeffery W Kelly
Journal:  J Org Chem       Date:  2003-11-28       Impact factor: 4.354

9.  Oxazole-based peptide macrocycles: a new class of G-quadruplex binding ligands.

Authors:  Katja Jantos; Raphaël Rodriguez; Sylvain Ladame; Pravin S Shirude; Shankar Balasubramanian
Journal:  J Am Chem Soc       Date:  2006-10-25       Impact factor: 15.419

10.  Spontaneity in the patellamide biosynthetic pathway.

Authors:  Bruce F Milne; Paul F Long; Antonio Starcevic; Daslav Hranueli; Marcel Jaspars
Journal:  Org Biomol Chem       Date:  2006-01-09       Impact factor: 3.876
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  8 in total

Review 1.  Thiazole and oxazole alkaloids: isolation and synthesis.

Authors:  Danilo Davyt; Gloria Serra
Journal:  Mar Drugs       Date:  2010-11-05       Impact factor: 5.118

2.  Cell penetrating thiazole peptides inhibit c-MYC expression via site-specific targeting of c-MYC G-quadruplex.

Authors:  Debasish Dutta; Manish Debnath; Diana Müller; Rakesh Paul; Tania Das; Irene Bessi; Harald Schwalbe; Jyotirmayee Dash
Journal:  Nucleic Acids Res       Date:  2018-06-20       Impact factor: 16.971

Review 3.  YcaO-Dependent Posttranslational Amide Activation: Biosynthesis, Structure, and Function.

Authors:  Brandon J Burkhart; Christopher J Schwalen; Greg Mann; James H Naismith; Douglas A Mitchell
Journal:  Chem Rev       Date:  2017-03-03       Impact factor: 60.622

Review 4.  Natural Products as Alternative Choices for P-Glycoprotein (P-gp) Inhibition.

Authors:  Saikat Dewanjee; Tarun K Dua; Niloy Bhattacharjee; Anup Das; Moumita Gangopadhyay; Ritu Khanra; Swarnalata Joardar; Muhammad Riaz; Vincenzo De Feo; Muhammad Zia-Ul-Haq
Journal:  Molecules       Date:  2017-05-25       Impact factor: 4.411

Review 5.  Marine Heterocyclic Compounds That Modulate Intracellular Calcium Signals: Chemistry and Synthesis Approaches.

Authors:  Paula González-Andrés; Laura Fernández-Peña; Carlos Díez-Poza; Carlos Villalobos; Lucía Nuñez; Asunción Barbero
Journal:  Mar Drugs       Date:  2021-01-31       Impact factor: 5.118

Review 6.  Possible Functional Roles of Patellamides in the Ascidian-Prochloron Symbiosis.

Authors:  Philipp Baur; Michael Kühl; Peter Comba; Lars Behrendt
Journal:  Mar Drugs       Date:  2022-02-02       Impact factor: 5.118

7.  Efficient Synthesis for a Wide Variety of Patellamide Derivatives and Phosphatase Activity of Copper-Patellamide Complexes.

Authors:  Philipp Baur; Peter Comba; Gunasekaran Velmurugan
Journal:  Chemistry       Date:  2022-03-18       Impact factor: 5.020

8.  Derivatisable Cyanobactin Analogues: A Semisynthetic Approach.

Authors:  Emilia Oueis; Catherine Adamson; Greg Mann; Hannes Ludewig; Philip Redpath; Marie Migaud; Nicholas J Westwood; James H Naismith
Journal:  Chembiochem       Date:  2015-11-10       Impact factor: 3.164
  8 in total

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