Total Synthesis of Glycinocins A-C

Leo Corcilius; Nabiha T Elias; Jessica L Ochoa; Roger G Linington; Richard J Payne

doi:10.1021/acs.joc.7b01959

Total Synthesis of Glycinocins A-C

J Org Chem. 2017 Dec 1;82(23):12778-12785. doi: 10.1021/acs.joc.7b01959. Epub 2017 Oct 27.

Authors

Leo Corcilius¹, Nabiha T Elias¹, Jessica L Ochoa², Roger G Linington^{2

3}, Richard J Payne¹

Affiliations

¹ School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
² Department of Chemistry and Biochemistry, University of California, Santa Cruz , 1156 High Street, Santa Cruz, California 95064, United States.
³ Department of Chemistry, Simon Fraser University , Burnaby, British Columbia V5A 1S6, Canada.

PMID: 28914054
DOI: 10.1021/acs.joc.7b01959

Abstract

The glycinocins are a class of calcium-dependent, acidic cyclolipopeptide antibiotics structurally related to the clinically approved daptomycin. Herein, we describe a divergent total synthesis of glycinocins A-C, which differ in the structure of a branched α,β-unsaturated fatty acyl moiety. The three natural products exhibited calcium-dependent antimicrobial activity against Staphylococcus aureus and Bacillus subtilis with MICs ranging from 5.5 to 17 μM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology
Bacillus subtilis / drug effects
Molecular Structure
Staphylococcus aureus / drug effects

Substances

Anti-Bacterial Agents