Total Synthesis and Configurational Revision of Mozamide A, a Hydroxy-Brunsvicamide
The marine cyclopeptide mozamide A, a member of the class of anabaenopeptin-type peptides, was synthesized for the first time via a convergent and flexible route. The installation of the substituted tryptophan moieties was accomplished at the very end of the synthesis and thus allows easy modificati...
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| Veröffentlicht in: | Journal of organic chemistry 2019-03, Vol.84 (5), p.2489-2500 |
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| container_title | Journal of organic chemistry |
| container_volume | 84 |
| creator | Junk, Lukas Kazmaier, Uli |
| description | The marine cyclopeptide mozamide A, a member of the class of anabaenopeptin-type peptides, was synthesized for the first time via a convergent and flexible route. The installation of the substituted tryptophan moieties was accomplished at the very end of the synthesis and thus allows easy modifications at this position. Comparison of the NMR data of the synthesized cyclopeptide with the natural product clearly indicates that the originally proposed structure of mozamide A cannot be correct. The synthesis of two other diastereomers allowed correction of the configuration of three amino acid building blocks. Mozamide A contains l-Val, d-Lys, and l-Ile (instead of d-Val, l-Lys, and l-allo-Ile) and is a hydroxylated brunsvicamide. |
| doi_str_mv | 10.1021/acs.joc.8b02836 |
| format | Article |
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Mozamide A contains l-Val, d-Lys, and l-Ile (instead of d-Val, l-Lys, and l-allo-Ile) and is a hydroxylated brunsvicamide.</description><subject>Animals</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Porifera</subject><subject>Protein Conformation</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kM9LwzAUx4Mobk7P3iRHQbvlR9M0xznUCRPBzXNI21QzumYm7bD-9UY7vfng8R68z_sePgCcYzTGiOCJyv14bfNxmiGS0uQADDEjKEoEig_BECFCIkoSOgAn3q9RKMbYMRhQxFloMQTLlW1UBZdd3bxpbzxUdQFnti7Na-tUY2wdrs96Z3xYoS3ho_1UG1NoOL2GCs67wtmPLrpxbe13Jv85nYKjUlVen-3nCLzc3a5m82jxdP8wmy4iRYVoojTJCNY0KyhBKcs4TwQrKM61KGnJKaeFinmmuSp5JuKYUkYCSWKBKGI5InQELvvcrbPvrfaN3Bif66pStbatlwSnMSMMYRbQSY_mznrvdCm3zmyU6yRG8tukDCZlMCn3JsPHxT68zTa6-ON_1QXgqgf6z9YFU_7fuC-NlX1c</recordid><startdate>20190301</startdate><enddate>20190301</enddate><creator>Junk, Lukas</creator><creator>Kazmaier, Uli</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><orcidid>https://orcid.org/0000-0001-9756-0589</orcidid></search><sort><creationdate>20190301</creationdate><title>Total Synthesis and Configurational Revision of Mozamide A, a Hydroxy-Brunsvicamide</title><author>Junk, Lukas ; Kazmaier, Uli</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-86b21e3bd32085b77695d31ce9f3f7373da47be7af7b94433523202490305c023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Animals</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Porifera</topic><topic>Protein Conformation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Junk, Lukas</creatorcontrib><creatorcontrib>Kazmaier, Uli</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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Junk, Lukas</au><au>Kazmaier, Uli</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis and Configurational Revision of Mozamide A, a Hydroxy-Brunsvicamide</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Nuclear Magnetic Resonance, Biomolecular Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Porifera Protein Conformation |
| title | Total Synthesis and Configurational Revision of Mozamide A, a Hydroxy-Brunsvicamide |
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