Abstract
A novel active gramicidin S analogue with smaller ring size, cyclo[-δ-Orn(-Val-Pro-d-Phe-H)-Leu-]2, was synthesized and examined the structure-activity relationship. Its analogue showed antibiotic activity against all Gram-positive microorganisms tested, and its activity was 1/2∼1/8 of that of gramicidin S. The present results indicated that both structures of cyclo(-δ-Orn-Leu-)2 and H-d-Phe-Pro-Val sequence play the important role for showing the antibiotic activity.
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Abbreviations
- Boc:
-
t-butoxycarbonyl
- Z:
-
benzyloxy carbonyl
- -OBzl:
-
-benzoxy
- EDCI:
-
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
- -ONSu:
-
N-hydroxysuccinimide ester
- HOBt:
-
1-hydroxybenzotriazole
- TFA:
-
trifluoroacetic acid
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Tamaki, M., Ishii, R., Kikuchi, S. et al. A Novel Active Analogue of Gramicidin S with Smaller Ring Size. J Antibiot 58, 293–295 (2005). https://doi.org/10.1038/ja.2005.37
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DOI: https://doi.org/10.1038/ja.2005.37