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      Total Synthesis of Septocylindrin B and C-Terminus Modified Analogues

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          Abstract

          The total synthesis is reported of the peptaibol Septocylindrin B which is related to the well documented channel forming peptaibol antibiotic Alamethicin. Several analogues were synthesized with a modified C-terminus, to investigate the SAR of the terminal residue Phaol. All these peptides were tested for their membrane perturbation properties by fluorescent dye leakage assay and for their antibacterial activity.

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          Isolation and purification of a new kalimantacin/batumin-related polyketide antibiotic and elucidation of its biosynthesis gene cluster.

          Wesley Mattheus, Ling-Jie Gao, Piet Herdewijn … (2010)
          Kal/bat, a polyketide, isolated to high purity (>95%) is characterized by strong and selective antibacterial activity against Staphylococcus species (minimum inhibitory concentration, 0.05 microg/mL), and no resistance was observed in strains already resistant to commonly used antibiotics. The kal/bat biosynthesis gene cluster was determined to a 62 kb genomic region of Pseudomonas fluorescens BCCM_ID9359. The kal/bat gene cluster consists of 16 open reading frames (ORF), encoding a hybrid PKS-NRPS system, extended with trans-acting tailoring functions. A full model for kal/bat biosynthesis is postulated and experimentally tested by gene inactivation, structural confirmation (using NMR spectroscopy), and complementation. The structural and microbiological study of biosynthetic kal/bat analogs revealed the importance of the carbamoyl group and 17-keto group for antibacterial activity. The mechanism of self-resistance lies within the production of an inactive intermediate, which is activated in a one-step enzymatic oxidation upon export. The genetic basis and biochemical elucidation of the biosynthesis pathway of this antibiotic will facilitate rational engineering for the design of novel structures with improved activities. This makes it a promising new therapeutic option to cope with multidrug-resistant clinical infections. Copyright 2010 Elsevier Ltd. All rights reserved.
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            Enterococci and streptococci.

            Sebastian Amyes (2007)
            Besides Staphylococcus aureus, other Gram-positive bacteria have become multidrug-resistant and cause therapeutic problems, particularly amongst hospitalised patients. The acquisition of vancomycin resistance by strains of Enterococcus faecium and Enterococcus faecalis is of particular concern and has resulted in treatment failures. Some of the infections caused by these bacteria do respond to treatment with new antibiotics that have been released in the last few years, however more options are required as not all enterococci are inherently susceptible and resistance is beginning to emerge amongst those that were susceptible. Resistance to commonly used antibiotics is also emerging in Streptococcus spp., particularly to the tetracyclines and macrolides. In both genera, multiresistant strains spread between patients and between hospitals. In the laboratory, these bacteria show considerable susceptibility to tigecycline, with little propensity to develop resistance, indicating that tigecycline could assume an important role in controlling infections caused by these Gram-positive bacteria.
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              Selective tert-butyl ester deprotection in the presence of acid labile protecting groups with use of ZnBr2.

              Zohreh Sajjadi, A. R. Kaul, Yann Brouillette … (2004)
              Chemoselective hydrolysis of tert-butyl esters in the presence of other acid-labile groups has been explored by employing alpha-amino esters and ZnBr(2) in DCM. Although N-Boc and N-trityl groups were found to be labile, PhF protected amines were compatible with these Lewis acid deprotection conditions such that a variety of N-(PhF)amino acids were prepared in good yields from their corresponding tert-butyl esters.
              Article 0 comments Cited 13 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Chandra Verma: Role: Editor
                Journal
                Journal ID (nlm-ta): PLoS One
                Journal ID (iso-abbrev): PLoS ONE
                Journal ID (publisher-id): plos
                Journal ID (pmc): plosone
                Title: PLoS ONE
                Publisher: Public Library of Science (San Francisco, USA )
                ISSN (Electronic): 1932-6203
                Publication date Collection: 2012
                Publication date (Electronic): 20 December 2012
                Volume: 7
                Issue: 12
                Electronic Location Identifier: e51708
                Affiliations
                [1 ]Molecular Design and Synthesis, Department of Chemistry, University of Leuven, Heverlee, Belgium
                [2 ]Department of Chemistry, University of Padova, Padova, Italy
                [3 ]Laboratory of Gene Technology, Biosystems Department, University of Leuven, Heverlee, Belgium
                Bioinformatics Institute, Singapore
                Author notes

                Competing Interests: The authors have declared that no competing interests exist.

                Conceived and designed the experiments: JN KN MDZ RL CL WMDB. Performed the experiments: JN KN MDZ CL. Analyzed the data: JN KN MDZ CL RL WMDB. Contributed reagents/materials/analysis tools: RL WMDB. Wrote the paper: JN KN MDZ RL CL WDB.

                Article
                Publisher ID: PONE-D-12-22370
                DOI: 10.1371/journal.pone.0051708
                PMC ID: 3527430
                PubMed ID: 23284749
                SO-VID: a4d1ec8b-0719-4a66-a0a0-8f8229bdca68
                Copyright statement: Copyright @ 2012
                License:

                This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

                History
                Date received : 26 July 2012
                Date accepted : 5 November 2012
                Page count
                Pages: 6
                Funding
                JN thanks the Institute for the Promotion of Innovation through Science and Technology in Flanders (Belgium, I.W.T., www.iwt.be) for financial support. KN thanks KU Leuven for financial support (Project OT/11/047/TBA). CL is supported by the IOF Knowledge Platform grant (“Functional peptidomics” IOF/KP/09/003) of the KU Leuven. This work was also partly supported by a grant of the FWO Vlaanderen (G.0599.11). The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.
                Categories
                Subject: Research Article
                Subject: Biology
                Subject: Biochemistry
                Subject: Cytochemistry
                Subject: Cell Membrane
                Subject: Membrane Characteristics
                Subject: Chemistry
                Subject: Chemical Reactions
                Subject: Synthesis
                Subject: Medicinal Chemistry
                Subject: Organic Chemistry
                Subject: Organic Acids
                Subject: Amino Acids
                Subject: Organic Compounds
                Subject: Amides
                Subject: Organic Synthesis
                Subject: Physical Organic Chemistry
                Subject: Synthetic Chemistry
                Subject: Organic Synthesis

                ScienceOpen disciplines: Uncategorized
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                ScienceOpen disciplines: Uncategorized

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