Total Synthesis and Determination of the Absolute Configuration of Vinylamycin

Zhantao Yang; Guang Yang; Meiyan Ma; Jiangnan Li; Jianwei Liu; Jinghan Wang; Shende Jiang; Quan Zhang; Yue Chen

doi:10.1021/acs.orglett.5b02809

Total Synthesis and Determination of the Absolute Configuration of Vinylamycin

Org Lett. 2015 Dec 4;17(23):5725-7. doi: 10.1021/acs.orglett.5b02809. Epub 2015 Nov 2.

Authors

Zhantao Yang¹, Guang Yang¹, Meiyan Ma¹, Jiangnan Li², Jianwei Liu¹, Jinghan Wang¹, Shende Jiang², Quan Zhang¹, Yue Chen¹

Affiliations

¹ The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), and Tianjin Key Laboratory of Molecular Drug Research, Nankai University , Tianjin 300071, People's Republic of China.
² School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, People's Republic of China.

PMID: 26523486
DOI: 10.1021/acs.orglett.5b02809

Abstract

The absolute configurations of the three unknown chiral centers in vinylamycin were predicted according to the structural comparison with microtermolide A and rakicidin A, and then total syntheses of vinylamycin were applied to determine the three unknown chiral centers as 14R, 15R, and 16S.

Publication types

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

MeSH terms

Bacterial Proteins / chemical synthesis*
Bacterial Proteins / chemistry*
Depsipeptides / chemical synthesis*
Depsipeptides / chemistry*
Lipopeptides / chemical synthesis*
Lipopeptides / chemistry
Molecular Structure
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Stereoisomerism

Substances

Bacterial Proteins
Depsipeptides
Lipopeptides
Peptides, Cyclic
microtermolide A
vinylamycin
rakicidins