Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids
[reaction: see text] Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformatio...
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| Veröffentlicht in: | Organic letters 2006-05, Vol.8 (11), p.2421-2424 |
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| creator | Vergne, Carine Boury-Esnault, Nicole Perez, Thierry Martin, Marie-Thérèse Adeline, Marie-Thérèse Tran Huu Dau, Elise Al-Mourabit, Ali |
| description | [reaction: see text] Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10). |
| doi_str_mv | 10.1021/ol0608092 |
| format | Article |
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Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0608092</identifier><identifier>PMID: 16706541</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkaloids - chemistry ; Alkaloids - metabolism ; Animals ; Axinella - chemistry ; Chemical Sciences ; Molecular Structure ; Organic chemistry ; Oxidation-Reduction ; Peptides, Cyclic - chemistry ; Piperazines - chemistry ; Piperazines - isolation & purification</subject><ispartof>Organic letters, 2006-05, Vol.8 (11), p.2421-2424</ispartof><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-1762-6910 ; 0000-0003-1728-6749 ; 0000-0003-1826-9318</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,778,782,883,27907,27908</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16706541$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00078488$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Vergne, Carine</creatorcontrib><creatorcontrib>Boury-Esnault, Nicole</creatorcontrib><creatorcontrib>Perez, Thierry</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Adeline, Marie-Thérèse</creatorcontrib><creatorcontrib>Tran Huu Dau, Elise</creatorcontrib><creatorcontrib>Al-Mourabit, Ali</creatorcontrib><title>Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>[reaction: see text] Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - metabolism</subject><subject>Animals</subject><subject>Axinella - chemistry</subject><subject>Chemical Sciences</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - isolation & purification</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkdFuFCEUhonR2Fq98AUMV8ZNOgoMM8N4N1mrNdmoF-rt5Ayc2cUyA8Js4_YtfaOyaW0MIcCXj5P_ACEvOXvLmeDvvGM1U6wVj8gpr0RZNKwSjx_2NTshz1L6xRjPpH1KTnidaSX5Kfn7E2MADZM1mGhXfDinQBP-3uOskfqRrjn_UlFjr3DxwQaMcGPnrEZ0sNh5S_VBO__mW_RFniu6-P9IF7erczpGP9Flh3SCmO_SFPy8Rdr9yQfngF6DRoeLfU-DT8kODulg_RbnzDQNEfU-Jh_TMU44xOgdFqLIkWdvc264yYCCuwLnrUnPyZMRXMIX9-sZ-fHx4vv6sth8_fR53W2KnZDlUlQIpmlrkUcztlI1oIZ2BIajlGYwRpVaDsIAk3yQGpVuQTamrUrVcF0pKM_I6q7uDlwfos3NHXoPtr_sNv2RMcYaJZW65tl9feeG6PPTpqWfbNLH5mf0-9TXTasEL1UWX92L-2FC81D334eVt9usmck</recordid><startdate>20060525</startdate><enddate>20060525</enddate><creator>Vergne, Carine</creator><creator>Boury-Esnault, Nicole</creator><creator>Perez, Thierry</creator><creator>Martin, Marie-Thérèse</creator><creator>Adeline, Marie-Thérèse</creator><creator>Tran Huu Dau, Elise</creator><creator>Al-Mourabit, Ali</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>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-1762-6910</orcidid><orcidid>https://orcid.org/0000-0003-1728-6749</orcidid><orcidid>https://orcid.org/0000-0003-1826-9318</orcidid></search><sort><creationdate>20060525</creationdate><title>Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids</title><author>Vergne, Carine ; Boury-Esnault, Nicole ; Perez, Thierry ; Martin, Marie-Thérèse ; Adeline, Marie-Thérèse ; Tran Huu Dau, Elise ; Al-Mourabit, Ali</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-h243t-5ead79626267f9487a8b9fa0ef44dbdd83c4b2da041b4ce8c9a47d953871c58a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Alkaloids - chemistry</topic><topic>Alkaloids - metabolism</topic><topic>Animals</topic><topic>Axinella - chemistry</topic><topic>Chemical Sciences</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - isolation & purification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vergne, Carine</creatorcontrib><creatorcontrib>Boury-Esnault, Nicole</creatorcontrib><creatorcontrib>Perez, Thierry</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Adeline, Marie-Thérèse</creatorcontrib><creatorcontrib>Tran Huu Dau, Elise</creatorcontrib><creatorcontrib>Al-Mourabit, Ali</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vergne, Carine</au><au>Boury-Esnault, Nicole</au><au>Perez, Thierry</au><au>Martin, Marie-Thérèse</au><au>Adeline, Marie-Thérèse</au><au>Tran Huu Dau, Elise</au><au>Al-Mourabit, Ali</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2006-05-25</date><risdate>2006</risdate><volume>8</volume><issue>11</issue><spage>2421</spage><epage>2424</epage><pages>2421-2424</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>[reaction: see text] Four C(11)N(5) diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C(11)N(5) pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>16706541</pmid><doi>10.1021/ol0608092</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-1762-6910</orcidid><orcidid>https://orcid.org/0000-0003-1728-6749</orcidid><orcidid>https://orcid.org/0000-0003-1826-9318</orcidid></addata></record> |
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| ispartof | Organic letters, 2006-05, Vol.8 (11), p.2421-2424 |
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| source | MEDLINE; ACS Publications |
| subjects | Alkaloids - chemistry Alkaloids - metabolism Animals Axinella - chemistry Chemical Sciences Molecular Structure Organic chemistry Oxidation-Reduction Peptides, Cyclic - chemistry Piperazines - chemistry Piperazines - isolation & purification |
| title | Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids |
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