Total Synthesis of Glycinocins A-C

被引:12
作者
Corcilius, Leo [1 ]
Elias, Nabiha T. [1 ]
Ochoa, Jessica L. [2 ]
Linington, Roger G. [2 ,3 ]
Payne, Richard J. [1 ]
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
[2] Univ Calif Santa Cruz, Dept Chem & Biochem, 1156 High St, Santa Cruz, CA 95064 USA
[3] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
基金
加拿大自然科学与工程研究理事会; 澳大利亚研究理事会;
关键词
DAPTOMYCIN; LASPARTOMYCIN; RESISTANCE; MECHANISM;
D O I
10.1021/acs.joc.7b01959
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 alpha,beta-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 mu M.
引用
收藏
页码:12778 / 12785
页数:8
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