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Ohmyungsamycins A and B: Cytotoxic and Antimicrobial Cyclic Peptides Produced by Streptomyces sp from a Volcanic Island
Cited 82 time in
Web of Science
Cited 83 time in Scopus
- Authors
- Issue Date
- 2013-12
- Publisher
- American Chemical Society
- Citation
- Journal of Organic Chemistry, Vol.78 No.24, pp.12321-12329
- Abstract
- Ohmyungsamycins A and B (1 and 2), which are new cyclic peptides, were isolated from a marine bacterial strain belonging to the Streptomyces genus collected from a sand beach on Jeju, a volcanic island in the Republic of Korea. Based on the interpretation of the NMR, UV, and IR spectroscopic and MS data, the planar structures of 1 and 2 were elucidated as cyclic depsipeptides bearing unusual amino acid units, including N-methyl-4-methoxytrytophan, beta-hydroxyphenylalanine, and N,N-dimethylvaline. The absolute configurations of the a-carbons of the amino acid residues were determined using the advanced Marfey's method. The configurations of the additional stereogenic centers at the beta-carbons of the threonine, N-methylthreonine, and beta-hydroxyphenylalanine units were assigned by GITC (2,3,4,6-tetra-O-acetyl-D-oglucopyranosyl isothiocyanate) derivatization and the modified Mosher's method. We have developed a new method utilizing PGME (phenylglycine methyl ester) derivatization coupled with chromatographic analysis to determine the absolute configuration of N,N-dimethylvaline. Our first successful establishment of the absolute configuration of N,N-dimethylvaline using PGME will provide a general and convenient analytical method for determining the absolute configurations of amino acids with fully substituted amine groups. Ohmyungsamycins A and B showed significant inhibitory activities against diverse cancer cells as well as antibacterial effects.
- ISSN
- 0022-3263
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