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Issue 6, 2014
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A combined solid- and solution-phase approach provides convenient access to analogues of the calcium-dependent lipopeptide antibiotics

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Abstract

The calcium-dependent lipopeptide antibiotics represent a promising new class of antimicrobials for use in combating drug-resistant bacteria. At present, daptomycin is the only such lipopeptide used clinically and displays potent antimicrobial activity against a number of pathogenic Gram-positive bacteria. Given the increasing need for new antibiotics, practical synthetic access to unnatural analogues of daptomycin and related antimicrobial lipopeptides is of value. We here report an efficient synthetic route combining solid- and solution-phase techniques that allows for the rapid preparation of daptomycin analogues. Using this approach, four such analogues, including two enantiomeric variants, were synthesized and their antimicrobial activities and hydrolytic stabilities evaluated.

Graphical abstract: A combined solid- and solution-phase approach provides convenient access to analogues of the calcium-dependent lipopeptide antibiotics

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Supplementary files

Publication details

The article was received on 11 Nov 2013, accepted on 10 Dec 2013 and first published on 10 Dec 2013


Article type: Paper
DOI: 10.1039/C3OB42238K
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 913-918
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    A combined solid- and solution-phase approach provides convenient access to analogues of the calcium-dependent lipopeptide antibiotics

    P. '. Hart, L. H. J. Kleijn, G. de Bruin, S. F. Oppedijk, J. Kemmink and N. I. Martin, Org. Biomol. Chem., 2014, 12, 913
    DOI: 10.1039/C3OB42238K

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