期刊
CHEMBIOCHEM
卷 19, 期 24, 页码 2591-2597出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201800618
关键词
amphiphilicity; antibiotics; photopharmacology; photoswitchable peptides; secondary structure; S. aureus
资金
- Australian Research Council [CE140100003]
- National Computational Merit Allocation Scheme
- Australian Research Council [CE140100003] Funding Source: Australian Research Council
Gramicidin S is a naturally occurring antimicrobial cyclic peptide. Herein, we present a series of cyclic peptides based on gramicidin S that contain an azobenzene photoswitch to reversibly control secondary structure and, hence, antimicrobial activity. H-1 NMR spectroscopy and density functional theory calculations revealed a beta-sheet/beta-turn secondary structure for the cis configuration of each peptide, and an ill-defined conformation for all associated trans structures. The cis-enriched and trans-enriched photostationary states (PSSs) for peptides 1-3 were assayed against Staphylococcus aureus to reveal a clear relationship between well-defined secondary structure, amphiphilicity and optimal antimicrobial activity. Most notably, peptides 2 a and 2 b exhibited a fourfold difference in antimicrobial activity in the cis-enriched PSS over the trans-enriched equivalent. This photopharmacological approach allows antimicrobial activity to be regulated through photochemical control of the azobenzene photoswitch, thereby opening new avenues in the design and synthesis of future antibiotics.
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