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Ohmyungsamycins A and B: Cytotoxic and Antimicrobial Cyclic Peptides Produced by Streptomyces sp from a Volcanic Island
DC Field | Value | Language |
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dc.contributor.author | Um, Soohyun | - |
dc.contributor.author | Choi, Tae Joon | - |
dc.contributor.author | Kim, Heegyu | - |
dc.contributor.author | Kim, Byung Yong | - |
dc.contributor.author | Kim, Seong-Hwan | - |
dc.contributor.author | Lee, Sang Kook | - |
dc.contributor.author | Oh, Ki-Bong | - |
dc.contributor.author | Shin, Jongheon | - |
dc.contributor.author | Oh, Dong-Chan | - |
dc.date.accessioned | 2024-08-08T01:43:06Z | - |
dc.date.available | 2024-08-08T01:43:06Z | - |
dc.date.created | 2017-11-15 | - |
dc.date.created | 2017-11-15 | - |
dc.date.issued | 2013-12 | - |
dc.identifier.citation | Journal of Organic Chemistry, Vol.78 No.24, pp.12321-12329 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | https://hdl.handle.net/10371/207540 | - |
dc.description.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. | - |
dc.language | 영어 | - |
dc.publisher | American Chemical Society | - |
dc.title | Ohmyungsamycins A and B: Cytotoxic and Antimicrobial Cyclic Peptides Produced by Streptomyces sp from a Volcanic Island | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/jo401974g | - |
dc.citation.journaltitle | Journal of Organic Chemistry | - |
dc.identifier.wosid | 000329077900004 | - |
dc.identifier.scopusid | 2-s2.0-84890893801 | - |
dc.citation.endpage | 12329 | - |
dc.citation.number | 24 | - |
dc.citation.startpage | 12321 | - |
dc.citation.volume | 78 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Lee, Sang Kook | - |
dc.contributor.affiliatedAuthor | Oh, Ki-Bong | - |
dc.contributor.affiliatedAuthor | Shin, Jongheon | - |
dc.contributor.affiliatedAuthor | Oh, Dong-Chan | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | MARINE NATURAL-PRODUCTS | - |
dc.subject.keywordPlus | ABSOLUTE-CONFIGURATION | - |
dc.subject.keywordPlus | MASS-SPECTROMETRY | - |
dc.subject.keywordPlus | CARBOXYLIC-ACIDS | - |
dc.subject.keywordPlus | AMINO-ACIDS | - |
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