Literature DB >> 28590764

An Entirely Solid Phase Peptide Synthesis-Based Strategy for Synthesis of Gelatinase Biosynthesis-Activating Pheromone (GBAP) Analogue Libraries: Investigating the Structure-Activity Relationships of the Enterococcus faecalis Quorum Sensing Signal.

Dominic N McBrayer1, Brooke K Gantman1, Crissey D Cameron1, Yftah Tal-Gan1.   

Abstract

The development of an entirely solid-phase peptide synthesis (SPPS)-based synthesis of the quorum sensing signal gelatinase biosynthesis-activating pheromone (GBAP) from Enterococcus faecalis is reported. The method was used to prepare three libraries of analogues to investigate the structure-activity relationships (SARs) of the GBAP signal. The SAR studies revealed new characteristics of the GBAP signal and uncovered the most potent quorum sensing activator in E. faecalis known to date.

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Year:  2017        PMID： 28590764      PMCID： PMC5551036          DOI： 10.1021/acs.orglett.7b01444

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


  19 in total

1.  Chemical synthesis and biological activity of the gelatinase biosynthesis-activating pheromone of Enterococcus faecalis and its analogs.

Authors:  J Nakayama; Y Cao; T Horii; S Sakuda; H Nagasawa
Journal:  Biosci Biotechnol Biochem       Date:  2001-10       Impact factor: 2.043

2.  Characterization of fsr, a regulator controlling expression of gelatinase and serine protease in Enterococcus faecalis OG1RF.

Authors:  X Qin; K V Singh; G M Weinstock; B E Murray
Journal:  J Bacteriol       Date:  2001-06       Impact factor: 3.490

3.  Fast conventional Fmoc solid-phase peptide synthesis: a comparative study of different activators.

Authors:  Christina Ann Chantell; Michael Abayomi Onaiyekan; Mahendra Menakuru
Journal:  J Pept Sci       Date:  2011-12-07       Impact factor: 1.905

Review 4.  The rise of the Enterococcus: beyond vancomycin resistance.

Authors:  Cesar A Arias; Barbara E Murray
Journal:  Nat Rev Microbiol       Date:  2012-03-16       Impact factor: 60.633

Review 5.  Peptide pheromone signaling in Streptococcus and Enterococcus.

Authors:  Laura C Cook; Michael J Federle
Journal:  FEMS Microbiol Rev       Date:  2013-10-31       Impact factor: 16.408

6.  Effects of Enterococcus faecalis fsr genes on production of gelatinase and a serine protease and virulence.

Authors:  X Qin; K V Singh; G M Weinstock; B E Murray
Journal:  Infect Immun       Date:  2000-05       Impact factor: 3.441

7.  Development of a peptide antagonist against fsr quorum sensing of Enterococcus faecalis.

Authors:  Jiro Nakayama; Ryoji Yokohata; Mami Sato; Takashi Suzuki; Takahisa Matsufuji; Kenzo Nishiguchi; Takeshi Kawai; Yosuke Yamanaka; Koji Nagata; Masaru Tanokura; Kenji Sonomoto
Journal:  ACS Chem Biol       Date:  2013-02-07       Impact factor: 5.100

Review 8.  Advances in Fmoc solid-phase peptide synthesis.

Authors:  Raymond Behrendt; Peter White; John Offer
Journal:  J Pept Sci       Date:  2016-01       Impact factor: 1.905

Review 9.  Quorum sensing signal-response systems in Gram-negative bacteria.

Authors:  Kai Papenfort; Bonnie L Bassler
Journal:  Nat Rev Microbiol       Date:  2016-08-11       Impact factor: 60.633

Review 10.  Quorum quenching agents: resources for antivirulence therapy.

Authors:  Kaihao Tang; Xiao-Hua Zhang
Journal:  Mar Drugs       Date:  2014-05-30       Impact factor: 5.118
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  11 in total

1.  Unveiling the Importance of Amide Protons in CSP:ComD Interactions in Streptococcus pneumoniae.

Authors:  Bimal Koirala; Naiya R Phillips; Yftah Tal-Gan
Journal:  ACS Med Chem Lett       Date:  2019-04-30       Impact factor: 4.345

2.  Development of a Dominant Negative Competence-Stimulating Peptide (dnCSP) that Attenuates Streptococcus pneumoniae Infectivity in a Mouse Model of Acute Pneumonia.

Authors:  Bimal Koirala; Jingjun Lin; Gee W Lau; Yftah Tal-Gan
Journal:  Chembiochem       Date:  2018-10-23       Impact factor: 3.164

3.  N-Methylation of Amino Acids in Gelatinase Biosynthesis-Activating Pheromone Identifies Key Site for Stability Enhancement with Retention of the Enterococcus faecalis fsr Quorum Sensing Circuit Response.

Authors:  Dominic N McBrayer; Brooke K Gantman; Yftah Tal-Gan
Journal:  ACS Infect Dis       Date:  2019-04-19       Impact factor: 5.084

4.  Designing cyclic competence-stimulating peptide (CSP) analogs with pan-group quorum-sensing inhibition activity in Streptococcus pneumoniae.

Authors:  Yifang Yang; Jingjun Lin; Anthony Harrington; Gabriel Cornilescu; Gee W Lau; Yftah Tal-Gan
Journal:  Proc Natl Acad Sci U S A       Date:  2020-01-08       Impact factor: 11.205

5.  Structural Characterization of Competence-Stimulating Peptide Analogues Reveals Key Features for ComD1 and ComD2 Receptor Binding in Streptococcus pneumoniae.

Authors:  Yifang Yang; Gabriel Cornilescu; Yftah Tal-Gan
Journal:  Biochemistry       Date:  2018-08-28       Impact factor: 3.162

Review 6.  Development and utilization of peptide-based quorum sensing modulators in Gram-positive bacteria.

Authors:  Dominic N McBrayer; Crissey D Cameron; Yftah Tal-Gan
Journal:  Org Biomol Chem       Date:  2020-09-30       Impact factor: 3.876

7.  Rational Design of Potent Activators and Inhibitors of the Enterococcus faecalis Fsr Quorum Sensing Circuit.

Authors:  Dominic N McBrayer; Crissey D Cameron; Brooke K Gantman; Yftah Tal-Gan
Journal:  ACS Chem Biol       Date:  2018-09-07       Impact factor: 5.100

8.  Structure-Activity Relationships of the Competence Stimulating Peptide in Streptococcus mutans Reveal Motifs Critical for Membrane Protease SepM Recognition and ComD Receptor Activation.

Authors:  Chowdhury Raihan Bikash; Sally R Hamry; Yftah Tal-Gan
Journal:  ACS Infect Dis       Date:  2018-07-23       Impact factor: 5.084

9.  Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae.

Authors:  Bimal Koirala; Robert A Hillman; Erin K Tiwold; Michael A Bertucci; Yftah Tal-Gan
Journal:  Beilstein J Org Chem       Date:  2018-07-16       Impact factor: 2.883

10.  Biological Evaluation of Native Streptococcal Competence Stimulating Peptides Reveal Potential Crosstalk Between Streptococcus mitis and Streptococcus pneumoniae and a New Scaffold for the Development of S. pneumoniae Quorum Sensing Modulators.

Authors:  Tahmina Ahmed Milly; Yftah Tal-Gan
Journal:  RSC Chem Biol       Date:  2020-05-29
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