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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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Supplementary files

Article information


Submitted
29 May 2018
Accepted
03 Jul 2018
First published
06 Jul 2018

Org. Biomol. Chem., 2018,16, 5310-5320
Article type
Paper
Author version available

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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