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Issue 29, 2018
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Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics

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Abstract

The glycinocins are a class of calcium-dependent, acidic cyclolipopeptide antibiotics that are structurally related to the clinically approved antibiotic daptomycin. In this article, we describe the synthesis of a small library of glycinocin analogues that differ by variation in the exocyclic fatty acyl substituent. The glycinocin analogues were screened against a panel of Gram-positive bacteria (as well as Gram-negative P. aeruginosa). These analogues exhibited similar calcium-dependent activity to the parent natural products against Gram-positive bacteria but showed no activity against P. aeruginosa. The length of the fatty acid was shown to be important for optimal biological activity, while the hybridisation at the α,β position and branching within the fatty acyl chain had only subtle effects on activity.

Graphical abstract: Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics

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Publication details

The article was received on 29 May 2018, accepted on 03 Jul 2018 and first published on 06 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01268G
Citation: Org. Biomol. Chem., 2018,16, 5310-5320
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    Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics

    L. Corcilius, D. Y. Liu, J. L. Ochoa, R. G. Linington and R. J. Payne, Org. Biomol. Chem., 2018, 16, 5310
    DOI: 10.1039/C8OB01268G

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