Synthesis and antibiotic activity of a gramicidin S analogue containing bicyclic β-turn dipeptides
- 31 December 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1231-1234
- https://doi.org/10.1039/p19860001231
Abstract
In order to demonstrate the usefulness of a bicyclic dipeptide derivative designed to simulate the backbone conformation of a β-turn (type II′), the dipeptide (3S, 6S, 9R)-2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid has been incorporated into gramicidin S (GS) at the β-turns in place of the D-Phe-Pro sequences.The GS analogue exhibited equal antibacterial activity, and a closely similar c.d. spectrum, to that of GS, indicating that there are two β-turns in the biologically active conformation of GS. The method seems applicable to more flexible peptides of biological interest.This publication has 8 references indexed in Scilit:
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