Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 29, Pages 5310-5320Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob01268g
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Funding
- Australian Research Council Future Fellowship [FT130100150]
- Natural Sciences and Engineering Research Council of Canada [RGPIN-2016-03962]
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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 alpha,beta position and branching within the fatty acyl chain had only subtle effects on activity.
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