Literature DB >> 15957914

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

Radha S Narayan1, Michael S Vannieuwenhze.   

Abstract

[reaction: see text] Lantibiotics are a class of lanthionine (and/or beta-methyllanthionine)-containing peptides with antibioitic activity against Gram-positive bacteria. As part of our research effort directed toward the synthesis and mechanistic study of the lantibiotic peptide mersacidin (1), we report stereoselective syntheses of orthogonally protected beta-methylcysteine (beta-MeCys) and beta-methyllanthionine (beta-MeLan), two key nonnatural amino acid components of the mersacidin architecture.

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Year:  2005        PMID： 15957914      PMCID： PMC1351053          DOI： 10.1021/ol0507930

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


  9 in total

1.  Mersacidin, a new antibiotic from Bacillus. In vitro and in vivo antibacterial activity.

Authors:  S Chatterjee; D K Chatterjee; R H Jani; J Blumbach; B N Ganguli; N Klesel; M Limbert; G Seibert
Journal:  J Antibiot (Tokyo)       Date:  1992-06       Impact factor: 2.649

2.  A general asymmetric synthesis of syn- and anti-beta-substituted cysteine and serine derivatives.

Authors:  Chiyi Xiong; Wei Wang; Victor J Hruby
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

3.  Orthogonally protected lanthionines: synthesis and use for the solid-phase synthesis of an analogue of nisin ring C.

Authors:  Sarah Bregant; Alethea B Tabor
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

4.  The lantibiotic mersacidin inhibits peptidoglycan synthesis by targeting lipid II.

Authors:  H Brötz; G Bierbaum; K Leopold; P E Reynolds; H G Sahl
Journal:  Antimicrob Agents Chemother       Date:  1998-01       Impact factor: 5.191

5.  Biomimetic stereoselective formation of methyllanthionine.

Authors:  Hao Zhou; Wilfred A van der Donk
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

6.  Rapid synthesis of acyl transfer auxiliaries for cysteine-free native glycopeptide ligation.

Authors:  Derek Macmillan; David W Anderson
Journal:  Org Lett       Date:  2004-12-09       Impact factor: 6.005

7.  Approaches toward the total synthesis of the nine-membered thio-lactone core of griseoviridin.

Authors:  Xavier Moreau; Jean-Marc Campagne
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354

8.  Synthesis of orthogonally protected lanthionines.

Authors:  M Firouz Mohd Mustapa; Richard Harris; Nives Bulic-Subanovic; Susan L Elliott; Sarah Bregant; Marianne F A Groussier; Jessica Mould; Darren Schultz; Nathan A L Chubb; Piers R J Gaffney; Paul C Driscoll; Alethea B Tabor
Journal:  J Org Chem       Date:  2003-10-17       Impact factor: 4.354

9.  Mode of action of the lantibiotic mersacidin: inhibition of peptidoglycan biosynthesis via a novel mechanism?

Authors:  H Brötz; G Bierbaum; A Markus; E Molitor; H G Sahl
Journal:  Antimicrob Agents Chemother       Date:  1995-03       Impact factor: 5.191
  9 in total
  15 in total

1.  Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives.

Authors:  Shengxi Chen; Nour Eddine Fahmi; Ryan C Nangreave; Youcef Mehellou; Sidney M Hecht
Journal:  Bioorg Med Chem       Date:  2012-02-15       Impact factor: 3.641

2.  Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.

Authors:  David C Cranfill; Mark A Lipton
Journal:  Org Lett       Date:  2007-08-03       Impact factor: 6.005

3.  Stereoselective Lewis acid mediated (3+2) cycloadditions of N-H- and N-sulfonylaziridines with heterocumulenes.

Authors:  Robert A Craig; Nicholas R O'Connor; Alexander F G Goldberg; Brian M Stoltz
Journal:  Chemistry       Date:  2014-03-06       Impact factor: 5.236

4.  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

5.  Synthesis of nonproteinogenic amino acids to probe lantibiotic biosynthesis.

Authors:  Xingang Zhang; Weijuan Ni; Wilfred A van der Donk
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

6.  Synthesis of the AviMeCys-containing D-ring of mersacidin.

Authors:  Angela K Carrillo; Michael S VanNieuwenhze
Journal:  Org Lett       Date:  2012-02-01       Impact factor: 6.005

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

Authors:  Pablo García-Reynaga; Angela K Carrillo; Michael S VanNieuwenhze
Journal:  Org Lett       Date:  2012-02-01       Impact factor: 6.005

8.  Synthesis and applications of polyamine amino acid residues: improving the bioactivity of an analgesic neuropeptide, neurotensin.

Authors:  Liuyin Zhang; Hee-Kyoung Lee; Timothy H Pruess; H Steve White; Grzegorz Bulaj
Journal:  J Med Chem       Date:  2009-03-26       Impact factor: 7.446

9.  Gastrointestinal localization of metronidazole by a lactobacilli-inspired tetramic acid motif improves treatment outcomes in the hamster model of Clostridium difficile infection.

Authors:  Philip T Cherian; Xiaoqian Wu; Lei Yang; Jerrod S Scarborough; Aman P Singh; Zahidul A Alam; Richard E Lee; Julian G Hurdle
Journal:  J Antimicrob Chemother       Date:  2015-08-18       Impact factor: 5.790

10.  Use of lantibiotic synthetases for the preparation of bioactive constrained peptides.

Authors:  Matthew R Levengood; Wilfred A van der Donk
Journal:  Bioorg Med Chem Lett       Date:  2008-01-19       Impact factor: 2.823
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