Literature DB >> 22296268

Decarbonylative approach to the synthesis of enamides from amino acids: stereoselective synthesis of the (Z)-aminovinyl-D-cysteine unit of mersacidin.

Pablo García-Reynaga1, Angela K Carrillo, Michael S VanNieuwenhze.   

Abstract

The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.

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Year:  2012        PMID： 22296268      PMCID： PMC3307523          DOI： 10.1021/ol203399x

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


  22 in total

Review 1.  Chemistry and biology of salicylihalamide a and related compounds.

Authors:  Larry Yet
Journal:  Chem Rev       Date:  2003-11       Impact factor: 60.622

2.  Synthesis of Substrates and Biochemical Probes for Study of the Peptidoglycan Biosynthetic Pathway.

Authors:  Radha S Narayan; Michael S Vannieuwenhze
Journal:  European J Org Chem       Date:  2007-01-19

3.  Stereoselective additions of thiyl radicals to terminal ynamides.

Authors:  Biplab Banerjee; Dmitry N Litvinov; Junghoon Kang; Jennifer D Bettale; Steven L Castle
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Total synthesis and initial structure-function analysis of the potent V-ATPase inhibitors salicylihalamide A and related compounds.

Authors:  Yusheng Wu; Xibin Liao; Ruifang Wang; Xiao-Song Xie; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2002-04-03       Impact factor: 15.419

5.  Versatile and stereoselective syntheses of orthogonally protected beta-methylcysteine and beta-methyllanthionine.

Authors:  Radha S Narayan; Michael S Vannieuwenhze
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

6.  Modification of C-terminal peptides to form peptide enamides: synthesis of chondriamides A and C.

Authors:  X Wang; J A Porco
Journal:  J Org Chem       Date:  2001-11-30       Impact factor: 4.354

Review 7.  Biosynthesis of aminovinyl-cysteine-containing peptides and its application in the production of potential drug candidates.

Authors:  Clarissa S Sit; Sabesan Yoganathan; John C Vederas
Journal:  Acc Chem Res       Date:  2011-03-02       Impact factor: 22.384

8.  Enamides accessed from aminothioesters via a Pd(0)-catalyzed decarbonylative/β-hydride elimination sequence.

Authors:  Geanna K Min; Dácil Hernández; Anders T Lindhardt; Troels Skrydstrup
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

Review 9.  Lantibiotics: peptides of diverse structure and function.

Authors:  Joanne M Willey; Wilfred A van der Donk
Journal:  Annu Rev Microbiol       Date:  2007       Impact factor: 15.500

10.  Palladium-catalyzed amidation of enol triflates: a new synthesis of enamides.

Authors:  Debra J Wallace; David J Klauber; Cheng-yi Chen; Ralph P Volante
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  7 in total

1.  Carboxyl Analogue of Mutacin 1140, a Scaffold for Lead Antibacterial Discovery.

Authors:  Jerome Escano; Akshaya Ravichandran; Bita Salamat; Leif Smith
Journal:  Appl Environ Microbiol       Date:  2017-06-30       Impact factor: 4.792

2.  Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

Authors:  Ziran Li; Zachary Gentry; Brennan Murphy; Michael S VanNieuwenhze
Journal:  Org Lett       Date:  2019-03-11       Impact factor: 6.005

3.  Synthesis and Bioactivity of Diastereomers of the Virulence Lanthipeptide Cytolysin.

Authors:  Subha Mukherjee; Liujie Huo; Gabrielle N Thibodeaux; Wilfred A van der Donk
Journal:  Org Lett       Date:  2016-11-18       Impact factor: 6.005

4.  Biomimetic Synthesis of Cbz-(S)-Dolaphenine.

Authors:  Pablo García-Reynaga; Michael S Vannieuwenhze
Journal:  Tetrahedron Lett       Date:  2012-09-12       Impact factor: 2.415

5.  Irradiation-induced palladium-catalyzed decarboxylative desaturation enabled by a dual ligand system.

Authors:  Wan-Min Cheng; Rui Shang; Yao Fu
Journal:  Nat Commun       Date:  2018-12-06       Impact factor: 14.919

6.  Chemical synthesis of the lantibiotic lacticin 481 reveals the importance of lanthionine stereochemistry.

Authors:  Patrick J Knerr; Wilfred A van der Donk
Journal:  J Am Chem Soc       Date:  2013-05-03       Impact factor: 15.419

Review 7.  Lanthipeptides: chemical synthesis versus in vivo biosynthesis as tools for pharmaceutical production.

Authors:  Elvis Legala Ongey; Peter Neubauer
Journal:  Microb Cell Fact       Date:  2016-06-07       Impact factor: 5.328
  7 in total

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