Literature DB >> 19845392

Synthesis and antibacterial properties of (-)-nor-platencin.

Olga V Barykina1, Kerri L Rossi, Michael J Rybak, Barry B Snider.   

Abstract

An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.

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Year:  2009        PMID： 19845392      PMCID： PMC2789445          DOI： 10.1021/ol902194q

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


  34 in total

Review 1.  Synthesis of platensimycin.

Authors:  Konrad Tiefenbacher; Johann Mulzer
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy.

Authors:  Sheo B Singh; Hiranthi Jayasuriya; John G Ondeyka; Kithsiri B Herath; Chaowei Zhang; Deborah L Zink; Nancy N Tsou; Richard G Ball; Angela Basilio; Olga Genilloud; Maria Teresa Diez; Francisca Vicente; Fernando Pelaez; Katherine Young; Jun Wang
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

3.  Platensimycin is a selective FabF inhibitor with potent antibiotic properties.

Authors:  Jun Wang; Stephen M Soisson; Katherine Young; Wesley Shoop; Srinivas Kodali; Andrew Galgoci; Ronald Painter; Gopalakrishnan Parthasarathy; Yui S Tang; Richard Cummings; Sookhee Ha; Karen Dorso; Mary Motyl; Hiranthi Jayasuriya; John Ondeyka; Kithsiri Herath; Chaowei Zhang; Lorraine Hernandez; John Allocco; Angela Basilio; José R Tormo; Olga Genilloud; Francisca Vicente; Fernando Pelaez; Lawrence Colwell; Sang Ho Lee; Bruce Michael; Thomas Felcetto; Charles Gill; Lynn L Silver; Jeffery D Hermes; Ken Bartizal; John Barrett; Dennis Schmatz; Joseph W Becker; Doris Cully; Sheo B Singh
Journal:  Nature       Date:  2006-05-18       Impact factor: 49.962

4.  Synthesis and biological evaluation of platensimycin analogs.

Authors:  Hong C Shen; Fa-Xiang Ding; Sheo B Singh; Gopalakrishnan Parthasarathy; Stephen M Soisson; Sookhee N Ha; Xun Chen; Srinivas Kodali; Jun Wang; Karen Dorso; James R Tata; Milton L Hammond; Malcolm Maccoss; Steven L Colletti
Journal:  Bioorg Med Chem Lett       Date:  2009-02-07       Impact factor: 2.823

5.  Efforts towards the identification of simpler platensimycin analogues--the total synthesis of oxazinidinyl platensimycin.

Authors:  Jingxin Wang; Vincent Lee; Herman O Sintim
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

6.  Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties.

Authors:  Jun Wang; Srinivas Kodali; Sang Ho Lee; Andrew Galgoci; Ronald Painter; Karen Dorso; Fred Racine; Mary Motyl; Lorraine Hernandez; Elizabeth Tinney; Steven L Colletti; Kithsiri Herath; Richard Cummings; Oscar Salazar; Ignacio González; Angela Basilio; Francisca Vicente; Olga Genilloud; Fernando Pelaez; Hiranthi Jayasuriya; Katherine Young; Doris F Cully; Sheo B Singh
Journal:  Proc Natl Acad Sci U S A       Date:  2007-04-24       Impact factor: 11.205

7.  A nine-step total synthesis of (-)-platencin.

Authors:  Konrad Tiefenbacher; Johann Mulzer
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

Review 8.  Platensimycin: a promising antimicrobial targeting fatty acid synthesis.

Authors:  D T Manallack; I T Crosby; Y Khakham; B Capuano
Journal:  Curr Med Chem       Date:  2008       Impact factor: 4.530

9.  Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity.

Authors:  K C Nicolaou; Antonia F Stepan; Troy Lister; Ang Li; Ana Montero; G Scott Tria; Craig I Turner; Yefeng Tang; Jianhua Wang; Ross M Denton; David J Edmonds
Journal:  J Am Chem Soc       Date:  2008-09-05       Impact factor: 15.419

10.  Amino acid salt catalyzed intramolecular Robinson annulation.

Authors:  Pingfan Li; Hisashi Yamamoto
Journal:  Chem Commun (Camb)       Date:  2009-08-04       Impact factor: 6.222
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  4 in total

Review 1.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649

2.  Semisynthesis and Biological Evaluation of Platencin Thioether Derivatives: Dual FabF and FabH Inhibitors against MRSA.

Authors:  Yuling Li; Xiang Weng; Youchao Deng; Jian Pan; Saibin Zhu; Zhongqing Wen; Yanqiu Yuan; Shaowen Li; Ben Shen; Yanwen Duan; Yong Huang
Journal:  ACS Med Chem Lett       Date:  2021-02-15       Impact factor: 4.345

Review 3.  The use of platensimycin and platencin to fight antibiotic resistance.

Authors:  Adil M Allahverdiyev; Melahat Bagirova; Emrah Sefik Abamor; Sezen Canim Ates; Rabia Cakir Koc; Meral Miraloglu; Serhat Elcicek; Serkan Yaman; Gokce Unal
Journal:  Infect Drug Resist       Date:  2013-09-18       Impact factor: 4.003

Review 4.  A Review on Platensimycin: A Selective FabF Inhibitor.

Authors:  Manik Das; Partha Sakha Ghosh; Kuntal Manna
Journal:  Int J Med Chem       Date:  2016-01-28
  4 in total

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