Synthesis and structure-activity relationship studies of N-terminal analogues of the antimicrobial peptide tridecaptin A(1)
Chemical synthesis was used to increase the potency of the antimicrobial lipopeptide tridecaptin A1. Lipid tail modification proved to be an ideal platform for synthesizing structurally simpler analogues that are not readily accessible by isolation. The stereochemical elements of the tridecaptin A1...
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| Veröffentlicht in: | Journal of medicinal chemistry 2014-02, Vol.57 (3), p.1127-1131 |
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| container_end_page | 1131 |
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| container_issue | 3 |
| container_start_page | 1127 |
| container_title | Journal of medicinal chemistry |
| container_volume | 57 |
| creator | Cochrane, Stephen A Lohans, Christopher T Brandelli, Jeremy R Mulvey, George Armstrong, Glen D Vederas, John C |
| description | Chemical synthesis was used to increase the potency of the antimicrobial lipopeptide tridecaptin A1. Lipid tail modification proved to be an ideal platform for synthesizing structurally simpler analogues that are not readily accessible by isolation. The stereochemical elements of the tridecaptin A1 lipid tail are not essential for antimicrobial activity and could be replaced with hydrophobic aliphatic or aromatic groups. Some simpler analogues displayed potent antimicrobial activity against Gram-negative bacteria, including Campylobacter jejuni, Escherichia coli O157:H7, and multidrug resistant Klebsiella pneumoniae. |
| doi_str_mv | 10.1021/jm401779d |
| format | Article |
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| ispartof | Journal of medicinal chemistry, 2014-02, Vol.57 (3), p.1127-1131 |
| issn | 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antimicrobial Cationic Peptides - chemical synthesis Antimicrobial Cationic Peptides - chemistry Antimicrobial Cationic Peptides - pharmacology Drug Resistance, Bacterial Gram-Negative Bacteria - drug effects Hemolysis Hydrophobic and Hydrophilic Interactions Lipopeptides - chemical synthesis Lipopeptides - chemistry Lipopeptides - pharmacology Peptides - chemical synthesis Peptides - chemistry Peptides - pharmacology Stereoisomerism Structure-Activity Relationship |
| title | Synthesis and structure-activity relationship studies of N-terminal analogues of the antimicrobial peptide tridecaptin A(1) |
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