Ulleungamides A and B, Modified α,β-Dehydropipecolic Acid Containing Cyclic Depsipeptides from Streptomyces sp. KCB13F003
Two novel cyclic depsipeptides, ulleungamides A (1) and B (2), were isolated from cultures of terrestrial Streptomyces sp. Their structures were determined by analyses of spectroscopic data and various chemical transformations, including modified Mosher’s method, advanced Marfey’s method, PGME, GITC...
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| Veröffentlicht in: | Organic letters 2015-08, Vol.17 (16), p.4046-4049 |
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| creator | Son, Sangkeun Ko, Sung-Kyun Jang, Mina Lee, Jae Kyoung Ryoo, In-Ja Lee, Jung-Sook Lee, Kyung Ho Soung, Nak-Kyun Oh, Hyuncheol Hong, Young-Soo Kim, Bo Yeon Jang, Jae-Hyuk Ahn, Jong Seog |
| description | Two novel cyclic depsipeptides, ulleungamides A (1) and B (2), were isolated from cultures of terrestrial Streptomyces sp. Their structures were determined by analyses of spectroscopic data and various chemical transformations, including modified Mosher’s method, advanced Marfey’s method, PGME, GITC derivatizations, and Snatzke’s method. Ulleungamides were determined to be a new class of peptides bearing unprecedented units, such as 5-hydroxy-6-methyl-2,3-dehydropipecolic acid, 4,5-dihydroxy-6-methyl-2,3-dehydropipecolic acid, and amino-linked 2-isopropylsuccinic acid. Ulleungamide A displayed growth inhibitory activity against Staphylococcus aureus and Salmonella typhimurium without cytotoxicity. |
| doi_str_mv | 10.1021/acs.orglett.5b01969 |
| format | Article |
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Ulleungamides were determined to be a new class of peptides bearing unprecedented units, such as 5-hydroxy-6-methyl-2,3-dehydropipecolic acid, 4,5-dihydroxy-6-methyl-2,3-dehydropipecolic acid, and amino-linked 2-isopropylsuccinic acid. Ulleungamide A displayed growth inhibitory activity against Staphylococcus aureus and Salmonella typhimurium without cytotoxicity.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.5b01969</identifier><identifier>PMID: 26262430</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Depsipeptides - chemistry ; Depsipeptides - classification ; Depsipeptides - isolation & purification ; Depsipeptides - pharmacology ; Drug Screening Assays, Antitumor ; HeLa Cells ; Humans ; Microbial Sensitivity Tests ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Pipecolic Acids - chemistry ; Salmonella typhimurium - drug effects ; Staphylococcus aureus - drug effects ; Stereoisomerism ; Streptomyces - chemistry</subject><ispartof>Organic letters, 2015-08, Vol.17 (16), p.4046-4049</ispartof><rights>Copyright © American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-6bc330d807969f8d8ae52de52c85e42f241c765306cfc44f571f7385b7850f523</citedby><cites>FETCH-LOGICAL-a345t-6bc330d807969f8d8ae52de52c85e42f241c765306cfc44f571f7385b7850f523</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5b01969$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.5b01969$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26262430$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Son, Sangkeun</creatorcontrib><creatorcontrib>Ko, Sung-Kyun</creatorcontrib><creatorcontrib>Jang, Mina</creatorcontrib><creatorcontrib>Lee, Jae Kyoung</creatorcontrib><creatorcontrib>Ryoo, In-Ja</creatorcontrib><creatorcontrib>Lee, Jung-Sook</creatorcontrib><creatorcontrib>Lee, Kyung Ho</creatorcontrib><creatorcontrib>Soung, Nak-Kyun</creatorcontrib><creatorcontrib>Oh, Hyuncheol</creatorcontrib><creatorcontrib>Hong, Young-Soo</creatorcontrib><creatorcontrib>Kim, Bo Yeon</creatorcontrib><creatorcontrib>Jang, Jae-Hyuk</creatorcontrib><creatorcontrib>Ahn, Jong Seog</creatorcontrib><title>Ulleungamides A and B, Modified α,β-Dehydropipecolic Acid Containing Cyclic Depsipeptides from Streptomyces sp. KCB13F003</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Two novel cyclic depsipeptides, ulleungamides A (1) and B (2), were isolated from cultures of terrestrial Streptomyces sp. Their structures were determined by analyses of spectroscopic data and various chemical transformations, including modified Mosher’s method, advanced Marfey’s method, PGME, GITC derivatizations, and Snatzke’s method. Ulleungamides were determined to be a new class of peptides bearing unprecedented units, such as 5-hydroxy-6-methyl-2,3-dehydropipecolic acid, 4,5-dihydroxy-6-methyl-2,3-dehydropipecolic acid, and amino-linked 2-isopropylsuccinic acid. Ulleungamide A displayed growth inhibitory activity against Staphylococcus aureus and Salmonella typhimurium without cytotoxicity.</description><subject>Depsipeptides - chemistry</subject><subject>Depsipeptides - classification</subject><subject>Depsipeptides - isolation & purification</subject><subject>Depsipeptides - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pipecolic Acids - chemistry</subject><subject>Salmonella typhimurium - drug effects</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Stereoisomerism</subject><subject>Streptomyces - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtOwzAYhC0EoqVwAiTkJYum2HGcpMs2pYAoYgFdR64fxVUSBztZVJwKDtIz4T7oElmW7dHMWP8HwDVGA4xCfMe4Gxi7LGTTDOgC4WE8PAFdTEMSJIiGp8d7jDrgwrkVQtgrw3PQCWO_IoK64GteFLKtlqzUQjo4gqwScNyHL0ZopaWAm-_-5ieYyI-1sKbWteSm0ByOuBYwM1XDdKWrJczWfCtPZO28p252bcqaEr411r9NueZecfUAPmdjTKYIkUtwpljh5NXh7IH59P49ewxmrw9P2WgWMBLRJogXnBAkUpT4CVUqUiZpKPzmKZVRqMII8ySmBMVc8ShSNMEqISldJClFyiPogdt9b23NZytdk5facVkUrJKmdTn2iEKUkJ2V7K3cGuesVHltdcnsOsco31LPPfX8QD0_UPepm8MH7aKU4pj5w-wNd3vDNr0yra38vP9W_gKVd5FQ</recordid><startdate>20150821</startdate><enddate>20150821</enddate><creator>Son, Sangkeun</creator><creator>Ko, Sung-Kyun</creator><creator>Jang, Mina</creator><creator>Lee, Jae Kyoung</creator><creator>Ryoo, In-Ja</creator><creator>Lee, Jung-Sook</creator><creator>Lee, Kyung Ho</creator><creator>Soung, Nak-Kyun</creator><creator>Oh, Hyuncheol</creator><creator>Hong, Young-Soo</creator><creator>Kim, Bo Yeon</creator><creator>Jang, Jae-Hyuk</creator><creator>Ahn, Jong Seog</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150821</creationdate><title>Ulleungamides A and B, Modified α,β-Dehydropipecolic Acid Containing Cyclic Depsipeptides from Streptomyces sp. KCB13F003</title><author>Son, Sangkeun ; Ko, Sung-Kyun ; Jang, Mina ; Lee, Jae Kyoung ; Ryoo, In-Ja ; Lee, Jung-Sook ; Lee, Kyung Ho ; Soung, Nak-Kyun ; Oh, Hyuncheol ; Hong, Young-Soo ; Kim, Bo Yeon ; Jang, Jae-Hyuk ; Ahn, Jong Seog</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-6bc330d807969f8d8ae52de52c85e42f241c765306cfc44f571f7385b7850f523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Depsipeptides - chemistry</topic><topic>Depsipeptides - classification</topic><topic>Depsipeptides - isolation & purification</topic><topic>Depsipeptides - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pipecolic Acids - chemistry</topic><topic>Salmonella typhimurium - drug effects</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Stereoisomerism</topic><topic>Streptomyces - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Son, Sangkeun</creatorcontrib><creatorcontrib>Ko, Sung-Kyun</creatorcontrib><creatorcontrib>Jang, Mina</creatorcontrib><creatorcontrib>Lee, Jae Kyoung</creatorcontrib><creatorcontrib>Ryoo, In-Ja</creatorcontrib><creatorcontrib>Lee, Jung-Sook</creatorcontrib><creatorcontrib>Lee, Kyung Ho</creatorcontrib><creatorcontrib>Soung, Nak-Kyun</creatorcontrib><creatorcontrib>Oh, Hyuncheol</creatorcontrib><creatorcontrib>Hong, Young-Soo</creatorcontrib><creatorcontrib>Kim, Bo Yeon</creatorcontrib><creatorcontrib>Jang, Jae-Hyuk</creatorcontrib><creatorcontrib>Ahn, Jong Seog</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Son, Sangkeun</au><au>Ko, Sung-Kyun</au><au>Jang, Mina</au><au>Lee, Jae Kyoung</au><au>Ryoo, In-Ja</au><au>Lee, Jung-Sook</au><au>Lee, Kyung Ho</au><au>Soung, Nak-Kyun</au><au>Oh, Hyuncheol</au><au>Hong, Young-Soo</au><au>Kim, Bo Yeon</au><au>Jang, Jae-Hyuk</au><au>Ahn, Jong Seog</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ulleungamides A and B, Modified α,β-Dehydropipecolic Acid Containing Cyclic Depsipeptides from Streptomyces sp. KCB13F003</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-08-21</date><risdate>2015</risdate><volume>17</volume><issue>16</issue><spage>4046</spage><epage>4049</epage><pages>4046-4049</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Two novel cyclic depsipeptides, ulleungamides A (1) and B (2), were isolated from cultures of terrestrial Streptomyces sp. Their structures were determined by analyses of spectroscopic data and various chemical transformations, including modified Mosher’s method, advanced Marfey’s method, PGME, GITC derivatizations, and Snatzke’s method. Ulleungamides were determined to be a new class of peptides bearing unprecedented units, such as 5-hydroxy-6-methyl-2,3-dehydropipecolic acid, 4,5-dihydroxy-6-methyl-2,3-dehydropipecolic acid, and amino-linked 2-isopropylsuccinic acid. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2015-08, Vol.17 (16), p.4046-4049 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Depsipeptides - chemistry Depsipeptides - classification Depsipeptides - isolation & purification Depsipeptides - pharmacology Drug Screening Assays, Antitumor HeLa Cells Humans Microbial Sensitivity Tests Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pipecolic Acids - chemistry Salmonella typhimurium - drug effects Staphylococcus aureus - drug effects Stereoisomerism Streptomyces - chemistry |
| title | Ulleungamides A and B, Modified α,β-Dehydropipecolic Acid Containing Cyclic Depsipeptides from Streptomyces sp. KCB13F003 |
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