Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma sp
Eudistomides A (1) and B (2), two new cyclic peptides, were isolated from a Fijian ascidian Eudistoma sp. These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were dete...
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| Veröffentlicht in: | Journal of organic chemistry 2009-02, Vol.74 (3), p.1156-1162 |
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| container_title | Journal of organic chemistry |
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| creator | Whitson, Emily L Ratnayake, Anokha S Bugni, Tim S Harper, Mary Kay Ireland, Chris M |
| description | Eudistomides A (1) and B (2), two new cyclic peptides, were isolated from a Fijian ascidian Eudistoma sp. These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were determined using a combination of spectroscopic and chemical methods. Chiral HPLC analysis revealed that all five amino acid residues in 1 and 2 had the l-configuration. Total synthesis of eudistomides A (1) and B (2) confirmed the proposed structures. Enantioselective lipase-catalyzed hydrolysis of a mixture of C-35 acetoxy epimers indicated a 35R absolute configuration for 2. |
| doi_str_mv | 10.1021/jo8022582 |
| format | Article |
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These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were determined using a combination of spectroscopic and chemical methods. Chiral HPLC analysis revealed that all five amino acid residues in 1 and 2 had the l-configuration. Total synthesis of eudistomides A (1) and B (2) confirmed the proposed structures. 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Org. Chem</addtitle><description>Eudistomides A (1) and B (2), two new cyclic peptides, were isolated from a Fijian ascidian Eudistoma sp. These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were determined using a combination of spectroscopic and chemical methods. Chiral HPLC analysis revealed that all five amino acid residues in 1 and 2 had the l-configuration. Total synthesis of eudistomides A (1) and B (2) confirmed the proposed structures. Enantioselective lipase-catalyzed hydrolysis of a mixture of C-35 acetoxy epimers indicated a 35R absolute configuration for 2.</description><subject>Animals</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Exact sciences and technology</subject><subject>Lipopeptides - chemistry</subject><subject>Lipopeptides - isolation & purification</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Organic chemistry</subject><subject>Peptides</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - isolation & purification</subject><subject>Preparations and properties</subject><subject>Sequence Analysis, Protein</subject><subject>Tandem Mass Spectrometry</subject><subject>Urochordata - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkV1rFDEUhoModlu98A9IbhQKHT3JfGVuCmvZamHBi-p1OJsPm2UmGZMZYf-9aTtuFcxNwnuevOdwXkLeMPjAgLOP-yCA81rwZ2TFag5F00H1nKwgq0XJm_KEnKa0h3zqun5JTlgHdcmEWJHDTQo9Ti74C3o7xVlNczR008_K6UVGr-ntwU93JrlEg6WbWbs0hcFpk-j6of7pgm7dGEYzTg-qjWGgSK_d3qGn65Td7h9_fiJN4yvywmKfzOvlPiPfrzffrr4U26-fb67W2wKrspwKBRyxKVvc2dogCM2qCjWITjODWQTD27YxOyGMRkALFjrTVK3iVnGmdXlGLh99x3k3GK2MnyL2coxuwHiQAZ38t-LdnfwRfknetMC6Khu8Xwxi-DmbNMnBJWX6Hr0Jc5JNI1oo6y6D54-giiGlaOyxCQN5H5Q8BpXZt39P9UQuyWTg3QJgUtjbiF65dOQ4g1Z0HXviUKXsP0efl_mfhr8Bmqapew</recordid><startdate>20090206</startdate><enddate>20090206</enddate><creator>Whitson, Emily L</creator><creator>Ratnayake, Anokha S</creator><creator>Bugni, Tim S</creator><creator>Harper, Mary Kay</creator><creator>Ireland, Chris M</creator><general>American Chemical Society</general><scope>IQODW</scope><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><scope>5PM</scope></search><sort><creationdate>20090206</creationdate><title>Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma sp</title><author>Whitson, Emily L ; Ratnayake, Anokha S ; Bugni, Tim S ; Harper, Mary Kay ; Ireland, Chris M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a433t-c02aa637abf5ea08d144ad089d1eaabf0e2776eb88eda0af0f09e647c2fc21dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Animals</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Exact sciences and technology</topic><topic>Lipopeptides - chemistry</topic><topic>Lipopeptides - isolation & purification</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Organic chemistry</topic><topic>Peptides</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - isolation & purification</topic><topic>Preparations and properties</topic><topic>Sequence Analysis, Protein</topic><topic>Tandem Mass Spectrometry</topic><topic>Urochordata - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Whitson, Emily L</creatorcontrib><creatorcontrib>Ratnayake, Anokha S</creatorcontrib><creatorcontrib>Bugni, Tim S</creatorcontrib><creatorcontrib>Harper, Mary Kay</creatorcontrib><creatorcontrib>Ireland, Chris M</creatorcontrib><collection>Pascal-Francis</collection><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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Whitson, Emily L</au><au>Ratnayake, Anokha S</au><au>Bugni, Tim S</au><au>Harper, Mary Kay</au><au>Ireland, Chris M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma sp</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-02-06</date><risdate>2009</risdate><volume>74</volume><issue>3</issue><spage>1156</spage><epage>1162</epage><pages>1156-1162</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Eudistomides A (1) and B (2), two new cyclic peptides, were isolated from a Fijian ascidian Eudistoma sp. These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were determined using a combination of spectroscopic and chemical methods. Chiral HPLC analysis revealed that all five amino acid residues in 1 and 2 had the l-configuration. Total synthesis of eudistomides A (1) and B (2) confirmed the proposed structures. Enantioselective lipase-catalyzed hydrolysis of a mixture of C-35 acetoxy epimers indicated a 35R absolute configuration for 2.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19053188</pmid><doi>10.1021/jo8022582</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of organic chemistry, 2009-02, Vol.74 (3), p.1156-1162 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Chemistry Chromatography, High Pressure Liquid Exact sciences and technology Lipopeptides - chemistry Lipopeptides - isolation & purification Nuclear Magnetic Resonance, Biomolecular Organic chemistry Peptides Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Preparations and properties Sequence Analysis, Protein Tandem Mass Spectrometry Urochordata - chemistry |
| title | Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma sp |
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