Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species
Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enab...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2017-11, Vol.80 (11), p.3025-3031 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Son, Sangkeun Hong, Young-Soo Jang, Mina Heo, Kyung Taek Lee, Byeongsan Jang, Jun-Pil Kim, Jong-Won Ryoo, In-Ja Kim, Won-Gon Ko, Sung-Kyun Kim, Bo Yeon Jang, Jae-Hyuk Ahn, Jong Seog |
| description | Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey’s analysis, and GITC derivatization. The new peptides, featuring unusual amino acids 5-chloro-l-tryptophan and d-homoleucine, exhibited moderate antibacterial activities against Gram-positive pathogenic bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus. |
| doi_str_mv | 10.1021/acs.jnatprod.7b00660 |
| format | Article |
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KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey’s analysis, and GITC derivatization. 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Nat. Prod</addtitle><description>Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey’s analysis, and GITC derivatization. The new peptides, featuring unusual amino acids 5-chloro-l-tryptophan and d-homoleucine, exhibited moderate antibacterial activities against Gram-positive pathogenic bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus.</description><subject>Amino Acid Sequence</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Chromatography, Liquid</subject><subject>Flavins - metabolism</subject><subject>Genomics</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Hydrocarbons, Chlorinated</subject><subject>Methicillin Resistance - drug effects</subject><subject>Methicillin-Resistant Staphylococcus aureus - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Oxidoreductases - metabolism</subject><subject>Peptide Synthases - metabolism</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - isolation & purification</subject><subject>Staphylococcal Infections</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Streptomyces - chemistry</subject><subject>Streptomyces - genetics</subject><subject>Tryptophan - metabolism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kD1PwzAQhi0EoqXwDxDyyJJyTmw3GUv5lCoxAHPkOhdwldjBThD99xjaMjLdcM_7nu4h5JzBlEHKrpQO07VVfeddNZ2tAKSEAzJmIoVEQioOyRiYzJIsl3xETkJYA0AGhTgmo7SAPMsLMSb2Hq1rjQ7JjTefaOmNCdp9ot9QV9PFe-O8iUewoouNboymD_ilOux6U2Ggr02Dg31rN9rYQOdU2Ype09q7lir63PvIubiM5HOH2mA4JUe1agKe7eaEvN7dviwekuXT_eNivkwUZ7xPVKpZxitRcAE6ZyDyXBWQFahrzgFmDEBHJs_0SvKZZFpp5EwWQoFmasayCbnc9kY7HwOGvmzjX9g0yqIbQskKkQsOqeQR5VtUexeCx7rsvGmV35QMyh_TZTRd7k2XO9MxdrG7MKxarP5Ce7URgC3wG3eDt_Hh_zu_AWjFjhc</recordid><startdate>20171122</startdate><enddate>20171122</enddate><creator>Son, Sangkeun</creator><creator>Hong, Young-Soo</creator><creator>Jang, Mina</creator><creator>Heo, Kyung Taek</creator><creator>Lee, Byeongsan</creator><creator>Jang, Jun-Pil</creator><creator>Kim, Jong-Won</creator><creator>Ryoo, In-Ja</creator><creator>Kim, Won-Gon</creator><creator>Ko, Sung-Kyun</creator><creator>Kim, Bo Yeon</creator><creator>Jang, Jae-Hyuk</creator><creator>Ahn, Jong Seog</creator><general>American Chemical Society and American Society of Pharmacognosy</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><orcidid>https://orcid.org/0000-0001-7768-2239</orcidid><orcidid>https://orcid.org/0000-0002-4363-4252</orcidid></search><sort><creationdate>20171122</creationdate><title>Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species</title><author>Son, Sangkeun ; Hong, Young-Soo ; Jang, Mina ; Heo, Kyung Taek ; Lee, Byeongsan ; Jang, Jun-Pil ; Kim, Jong-Won ; Ryoo, In-Ja ; Kim, Won-Gon ; Ko, Sung-Kyun ; Kim, Bo Yeon ; Jang, Jae-Hyuk ; Ahn, Jong Seog</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-a2c134d59450c810588a9039ecf44007100ca2c83cb64761cace41695a0c1a713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Amino Acid Sequence</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Chromatography, Liquid</topic><topic>Flavins - metabolism</topic><topic>Genomics</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Hydrocarbons, Chlorinated</topic><topic>Methicillin Resistance - drug effects</topic><topic>Methicillin-Resistant Staphylococcus aureus - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Oxidoreductases - metabolism</topic><topic>Peptide Synthases - metabolism</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - isolation & purification</topic><topic>Staphylococcal Infections</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Streptomyces - chemistry</topic><topic>Streptomyces - genetics</topic><topic>Tryptophan - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Son, Sangkeun</creatorcontrib><creatorcontrib>Hong, Young-Soo</creatorcontrib><creatorcontrib>Jang, Mina</creatorcontrib><creatorcontrib>Heo, Kyung Taek</creatorcontrib><creatorcontrib>Lee, Byeongsan</creatorcontrib><creatorcontrib>Jang, Jun-Pil</creatorcontrib><creatorcontrib>Kim, Jong-Won</creatorcontrib><creatorcontrib>Ryoo, In-Ja</creatorcontrib><creatorcontrib>Kim, Won-Gon</creatorcontrib><creatorcontrib>Ko, Sung-Kyun</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Son, Sangkeun</au><au>Hong, Young-Soo</au><au>Jang, Mina</au><au>Heo, Kyung Taek</au><au>Lee, Byeongsan</au><au>Jang, Jun-Pil</au><au>Kim, Jong-Won</au><au>Ryoo, In-Ja</au><au>Kim, Won-Gon</au><au>Ko, Sung-Kyun</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>Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2017-11-22</date><risdate>2017</risdate><volume>80</volume><issue>11</issue><spage>3025</spage><epage>3031</epage><pages>3025-3031</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey’s analysis, and GITC derivatization. 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| ispartof | Journal of natural products (Washington, D.C.), 2017-11, Vol.80 (11), p.3025-3031 |
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| source | ACS Publications; MEDLINE |
| subjects | Amino Acid Sequence Anti-Bacterial Agents - chemistry Chromatography, Liquid Flavins - metabolism Genomics Gram-Positive Bacteria - drug effects Hydrocarbons, Chlorinated Methicillin Resistance - drug effects Methicillin-Resistant Staphylococcus aureus - drug effects Microbial Sensitivity Tests Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oxidoreductases - metabolism Peptide Synthases - metabolism Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Staphylococcal Infections Staphylococcus aureus - drug effects Streptomyces - chemistry Streptomyces - genetics Tryptophan - metabolism |
| title | Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species |
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