Literature DB >> 22612400

Solid-phase synthesis of lysobactin (katanosin B): insights into structure and function.

Edward A Hall1, Erkin Kuru, Michael S VanNieuwenhze.   

Abstract

The solid phase synthesis of the cyclic depsipeptide antibiotic lysobactin is described. The natural product was synthesized via a linear approach using mostly an Fmoc-strategy solid phase peptide synthesis (SPPS) with a single purification. A lysobactin analog has also been synthesized displaying nanomolar membrane disruption activity not seen with the natural product.

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Year:  2012        PMID: 22612400      PMCID: PMC3488444          DOI: 10.1021/ol300926d

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


  14 in total

1.  Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methicillin-resistant Staphylococcus aureus.

Authors:  H Maki; K Miura; Y Yamano
Journal:  Antimicrob Agents Chemother       Date:  2001-06       Impact factor: 5.191

2.  Membrane damage and microbial inactivation by chlorine in the absence and presence of a chlorine-demanding substrate.

Authors:  R Virto; P Mañas; I Alvarez; S Condon; J Raso
Journal:  Appl Environ Microbiol       Date:  2005-09       Impact factor: 4.792

3.  Isolation and characterization of katanosins A and B.

Authors:  J Shoji; H Hinoo; K Matsumoto; T Hattori; T Yoshida; S Matsuura; E Kondo
Journal:  J Antibiot (Tokyo)       Date:  1988-06       Impact factor: 2.649

4.  Mode of action of the peptide antibiotic nisin and influence on the membrane potential of whole cells and on cytoplasmic and artificial membrane vesicles.

Authors:  E Ruhr; H G Sahl
Journal:  Antimicrob Agents Chemother       Date:  1985-05       Impact factor: 5.191

5.  Total synthesis of lysobactin.

Authors:  Aikomari Guzman-Martinez; Ryan Lamer; Michael S VanNieuwenhze
Journal:  J Am Chem Soc       Date:  2007-04-14       Impact factor: 15.419

6.  New tris-alkoxycarbonyl arginine derivatives for peptide synthesis.

Authors:  Jan Izdebski; Tomasz Gers; Danuta Kunce; Paweł Markowski
Journal:  J Pept Sci       Date:  2005-01       Impact factor: 1.905

7.  DEPBT as an efficient coupling reagent for amide bond formation with remarkable resistance to racemization.

Authors:  Yun-Hua Ye; Haitao Li; Xiaohui Jiang
Journal:  Biopolymers       Date:  2005       Impact factor: 2.505

8.  An Operationally Simple and Efficient Synthesis of Orthogonally Protected L-threo-beta-Hydroxyasparagine.

Authors:  Aikomari Guzmán-Martinez; Michael S Vannieuwenhze
Journal:  Synlett       Date:  2007-06-01       Impact factor: 2.454

9.  Superoxide generation by human neutrophils induced by low doses of Escherichia coli hemolysin.

Authors:  S Bhakdi; E Martin
Journal:  Infect Immun       Date:  1991-09       Impact factor: 3.441

10.  Lysobactin, a novel antibacterial agent produced by Lysobacter sp. II. Biological properties.

Authors:  D P Bonner; J O'Sullivan; S K Tanaka; J M Clark; R R Whitney
Journal:  J Antibiot (Tokyo)       Date:  1988-12       Impact factor: 2.649

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  2 in total

1.  The Mechanism of Action of Lysobactin.

Authors:  Wonsik Lee; Kaitlin Schaefer; Yuan Qiao; Veerasak Srisuknimit; Heinrich Steinmetz; Rolf Müller; Daniel Kahne; Suzanne Walker
Journal:  J Am Chem Soc       Date:  2015-12-24       Impact factor: 15.419

Review 2.  Advances in MRSA drug discovery: where are we and where do we need to be?

Authors:  Michio Kurosu; Shajila Siricilla; Katsuhiko Mitachi
Journal:  Expert Opin Drug Discov       Date:  2013-07-06       Impact factor: 6.098

  2 in total

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