Literature DB >> 27934350

Synthesis and Bioactivity of Diastereomers of the Virulence Lanthipeptide Cytolysin.

Subha Mukherjee1, Liujie Huo1, Gabrielle N Thibodeaux1, Wilfred A van der Donk1.   

Abstract

Cytolysin, a two-component lanthipeptide comprising cytolysin S (CylLS″) and cytolysin L (CylLL″), is the only family member to exhibit lytic activity against mammalian cells in addition to synergistic antimicrobial activity. A subset of the thioether cross-links of CylLS″ and CylLL″ have ll stereochemistry instead of the canonical dl stereochemistry in all previously characterized lanthipeptides. The synthesis of a CylLS″ variant with dl stereochemistry is reported. Its antimicrobial activity was found to be decreased, but not its lytic activity against red blood cells. Hence, the unusual ll stereochemistry is not responsible for the lytic activity.

Entities:  

Mesh：

Substances：

Year:  2016        PMID： 27934350      PMCID： PMC5269379          DOI： 10.1021/acs.orglett.6b03246

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


  26 in total

Review 1.  The Enterococcus faecalis cytolysin: a novel toxin active against eukaryotic and prokaryotic cells.

Authors:  Phillip S Coburn; Michael S Gilmore
Journal:  Cell Microbiol       Date:  2003-10       Impact factor: 3.715

2.  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

3.  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

4.  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

5.  Synthesis of the lantibiotic lactocin S using peptide cyclizations on solid phase.

Authors:  Avena C Ross; Hongqiang Liu; Vijaya R Pattabiraman; John C Vederas
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

6.  Concise preparation of tetra-orthogonally protected (2S,6R)-lanthionines.

Authors:  Nathaniel I Martin
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

Review 7.  Two-peptide lantibiotics: a medical perspective.

Authors:  Elaine M Lawton; R Paul Ross; Colin Hill; Paul D Cotter
Journal:  Mini Rev Med Chem       Date:  2007-12       Impact factor: 3.862

Review 8.  Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature.

Authors:  Paul G Arnison; Mervyn J Bibb; Gabriele Bierbaum; Albert A Bowers; Tim S Bugni; Grzegorz Bulaj; Julio A Camarero; Dominic J Campopiano; Gregory L Challis; Jon Clardy; Paul D Cotter; David J Craik; Michael Dawson; Elke Dittmann; Stefano Donadio; Pieter C Dorrestein; Karl-Dieter Entian; Michael A Fischbach; John S Garavelli; Ulf Göransson; Christian W Gruber; Daniel H Haft; Thomas K Hemscheidt; Christian Hertweck; Colin Hill; Alexander R Horswill; Marcel Jaspars; Wendy L Kelly; Judith P Klinman; Oscar P Kuipers; A James Link; Wen Liu; Mohamed A Marahiel; Douglas A Mitchell; Gert N Moll; Bradley S Moore; Rolf Müller; Satish K Nair; Ingolf F Nes; Gillian E Norris; Baldomero M Olivera; Hiroyasu Onaka; Mark L Patchett; Joern Piel; Martin J T Reaney; Sylvie Rebuffat; R Paul Ross; Hans-Georg Sahl; Eric W Schmidt; Michael E Selsted; Konstantin Severinov; Ben Shen; Kaarina Sivonen; Leif Smith; Torsten Stein; Roderich D Süssmuth; John R Tagg; Gong-Li Tang; Andrew W Truman; John C Vederas; Christopher T Walsh; Jonathan D Walton; Silke C Wenzel; Joanne M Willey; Wilfred A van der Donk
Journal:  Nat Prod Rep       Date:  2013-01       Impact factor: 13.423

Review 9.  Structure, function, and biology of the Enterococcus faecalis cytolysin.

Authors:  Daria Van Tyne; Melissa J Martin; Michael S Gilmore
Journal:  Toxins (Basel)       Date:  2013-04-29       Impact factor: 4.546

10.  Substrate control in stereoselective lanthionine biosynthesis.

Authors:  Weixin Tang; Gonzalo Jiménez-Osés; K N Houk; Wilfred A van der Donk
Journal:  Nat Chem       Date:  2014-11-24       Impact factor: 24.427
View more
  6 in total

Review 1.  Mechanistic Understanding of Lanthipeptide Biosynthetic Enzymes.

Authors:  Lindsay M Repka; Jonathan R Chekan; Satish K Nair; Wilfred A van der Donk
Journal:  Chem Rev       Date:  2017-01-30       Impact factor: 60.622

2.  A Chemical Biology Approach to Understanding Molecular Recognition of Lipid II by Nisin(1-12): Synthesis and NMR Ensemble Analysis of Nisin(1-12) and Analogues.

Authors:  Rachael Dickman; Emma Danelius; Serena A Mitchell; D Flemming Hansen; Máté Erdélyi; Alethea B Tabor
Journal:  Chemistry       Date:  2019-10-10       Impact factor: 5.236

3.  Unexpected Methyllanthionine Stereochemistry in the Morphogenetic Lanthipeptide SapT.

Authors:  Raymond Sarksian; Julian D Hegemann; Max A Simon; Jeella Z Acedo; Wilfred A van der Donk
Journal:  J Am Chem Soc       Date:  2022-03-30       Impact factor: 16.383

4.  Divergent Evolution of Lanthipeptide Stereochemistry.

Authors:  Raymond Sarksian; Wilfred A van der Donk
Journal:  ACS Chem Biol       Date:  2022-08-24       Impact factor: 4.634

5.  Structure-Activity Relationships of the Enterococcal Cytolysin.

Authors:  Imran R Rahman; Alondra Sanchez; Weixin Tang; Wilfred A van der Donk
Journal:  ACS Infect Dis       Date:  2021-07-15       Impact factor: 5.578

6.  Genome mining, isolation, chemical synthesis and biological evaluation of a novel lanthipeptide, tikitericin, from the extremophilic microorganism Thermogemmatispora strain T81.

Authors:  Buzhe Xu; Emma J Aitken; Benjamin P Baker; Claire A Turner; Joanne E Harvey; Matthew B Stott; Jean F Power; Paul W R Harris; Robert A Keyzers; Margaret A Brimble
Journal:  Chem Sci       Date:  2018-08-20       Impact factor: 9.825
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.