Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water...
Gespeichert in:
Veröffentlicht in: | Chemical science (Cambridge) 2017-03, Vol.8 (3), p.2039-2046 |
---|---|
Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 2046 |
---|---|
container_issue | 3 |
container_start_page | 2039 |
container_title | Chemical science (Cambridge) |
container_volume | 8 |
creator | Corr, M J Sharma, S V Pubill-Ulldemolins, C Bown, R T Poirot, P Smith, D R M Cartmell, C Abou Fayad, A Goss, R J M |
description | The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite. |
doi_str_mv | 10.1039/c6sc04423a |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1893552889</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1893552889</sourcerecordid><originalsourceid>FETCH-LOGICAL-c463t-cba16e128b012c8ade8e5415c8455fe69735af7bc6bf3b841f937eb8e2dd6e423</originalsourceid><addsrcrecordid>eNqFkc9u3CAQxlHVqIk2e8kDVByrqk4MGNZWT9Gq-SNF6mGTszWG8S6VF1zAifJsebmQzXYP7aFzmQH9-Bh9HyFnrDxnpWgutIq6rCou4AM54WXFCiVF8_Ew8_KYzGP8VeYSgkm--ESOeV1JJjg_IS8r7_wa4sYGoMY-Yoi2txqS9Y76nk5uDD6hTmjoBgafwvOY_LgBF7_9dUG1dwmss25NU7AjjskajN8pOEPX6DAcVIE6fKLJUwdpCki74Le-2B1goPlHM-m0e2dT_Gct6-gTJAyn5KiHIeJ832fk4erH_fKmuPt5fbu8vCt0pUQqdAdMIeN1VzKuazBYo6yY1NkE2aNqFkJCv-i06nrR1RXrG7HArkZujMLs7Ix8edfNi_2eMKZ2a6PGYQCHfootqxshJa9z-z-a9RmXQmX06zuqg48xYN-OwW4hPLesbN-ibZdqtdxFe5nhz3vdqduiOaB_ghSvE4CkuQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1884112536</pqid></control><display><type>article</type><title>Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water</title><source>DOAJ Directory of Open Access Journals</source><source>PubMed Central Open Access</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><creator>Corr, M J ; Sharma, S V ; Pubill-Ulldemolins, C ; Bown, R T ; Poirot, P ; Smith, D R M ; Cartmell, C ; Abou Fayad, A ; Goss, R J M</creator><creatorcontrib>Corr, M J ; Sharma, S V ; Pubill-Ulldemolins, C ; Bown, R T ; Poirot, P ; Smith, D R M ; Cartmell, C ; Abou Fayad, A ; Goss, R J M</creatorcontrib><description>The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c6sc04423a</identifier><identifier>PMID: 28451322</identifier><language>eng</language><publisher>England</publisher><subject>Biosynthesis ; Blending ; Bromination ; Cross coupling ; Metabolites ; Natural products ; Precursors ; Synthesis (chemistry)</subject><ispartof>Chemical science (Cambridge), 2017-03, Vol.8 (3), p.2039-2046</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c463t-cba16e128b012c8ade8e5415c8455fe69735af7bc6bf3b841f937eb8e2dd6e423</citedby><cites>FETCH-LOGICAL-c463t-cba16e128b012c8ade8e5415c8455fe69735af7bc6bf3b841f937eb8e2dd6e423</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,782,786,866,27931,27932</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28451322$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Corr, M J</creatorcontrib><creatorcontrib>Sharma, S V</creatorcontrib><creatorcontrib>Pubill-Ulldemolins, C</creatorcontrib><creatorcontrib>Bown, R T</creatorcontrib><creatorcontrib>Poirot, P</creatorcontrib><creatorcontrib>Smith, D R M</creatorcontrib><creatorcontrib>Cartmell, C</creatorcontrib><creatorcontrib>Abou Fayad, A</creatorcontrib><creatorcontrib>Goss, R J M</creatorcontrib><title>Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.</description><subject>Biosynthesis</subject><subject>Blending</subject><subject>Bromination</subject><subject>Cross coupling</subject><subject>Metabolites</subject><subject>Natural products</subject><subject>Precursors</subject><subject>Synthesis (chemistry)</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkc9u3CAQxlHVqIk2e8kDVByrqk4MGNZWT9Gq-SNF6mGTszWG8S6VF1zAifJsebmQzXYP7aFzmQH9-Bh9HyFnrDxnpWgutIq6rCou4AM54WXFCiVF8_Ew8_KYzGP8VeYSgkm--ESOeV1JJjg_IS8r7_wa4sYGoMY-Yoi2txqS9Y76nk5uDD6hTmjoBgafwvOY_LgBF7_9dUG1dwmss25NU7AjjskajN8pOEPX6DAcVIE6fKLJUwdpCki74Le-2B1goPlHM-m0e2dT_Gct6-gTJAyn5KiHIeJ832fk4erH_fKmuPt5fbu8vCt0pUQqdAdMIeN1VzKuazBYo6yY1NkE2aNqFkJCv-i06nrR1RXrG7HArkZujMLs7Ix8edfNi_2eMKZ2a6PGYQCHfootqxshJa9z-z-a9RmXQmX06zuqg48xYN-OwW4hPLesbN-ibZdqtdxFe5nhz3vdqduiOaB_ghSvE4CkuQ</recordid><startdate>20170301</startdate><enddate>20170301</enddate><creator>Corr, M J</creator><creator>Sharma, S V</creator><creator>Pubill-Ulldemolins, C</creator><creator>Bown, R T</creator><creator>Poirot, P</creator><creator>Smith, D R M</creator><creator>Cartmell, C</creator><creator>Abou Fayad, A</creator><creator>Goss, R J M</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope></search><sort><creationdate>20170301</creationdate><title>Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water</title><author>Corr, M J ; Sharma, S V ; Pubill-Ulldemolins, C ; Bown, R T ; Poirot, P ; Smith, D R M ; Cartmell, C ; Abou Fayad, A ; Goss, R J M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c463t-cba16e128b012c8ade8e5415c8455fe69735af7bc6bf3b841f937eb8e2dd6e423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Biosynthesis</topic><topic>Blending</topic><topic>Bromination</topic><topic>Cross coupling</topic><topic>Metabolites</topic><topic>Natural products</topic><topic>Precursors</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Corr, M J</creatorcontrib><creatorcontrib>Sharma, S V</creatorcontrib><creatorcontrib>Pubill-Ulldemolins, C</creatorcontrib><creatorcontrib>Bown, R T</creatorcontrib><creatorcontrib>Poirot, P</creatorcontrib><creatorcontrib>Smith, D R M</creatorcontrib><creatorcontrib>Cartmell, C</creatorcontrib><creatorcontrib>Abou Fayad, A</creatorcontrib><creatorcontrib>Goss, R J M</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Corr, M J</au><au>Sharma, S V</au><au>Pubill-Ulldemolins, C</au><au>Bown, R T</au><au>Poirot, P</au><au>Smith, D R M</au><au>Cartmell, C</au><au>Abou Fayad, A</au><au>Goss, R J M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2017-03-01</date><risdate>2017</risdate><volume>8</volume><issue>3</issue><spage>2039</spage><epage>2046</epage><pages>2039-2046</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.</abstract><cop>England</cop><pmid>28451322</pmid><doi>10.1039/c6sc04423a</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2041-6520 |
ispartof | Chemical science (Cambridge), 2017-03, Vol.8 (3), p.2039-2046 |
issn | 2041-6520 2041-6539 |
language | eng |
recordid | cdi_proquest_miscellaneous_1893552889 |
source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
subjects | Biosynthesis Blending Bromination Cross coupling Metabolites Natural products Precursors Synthesis (chemistry) |
title | Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-05T12%3A28%3A43IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sonogashira%20diversification%20of%20unprotected%20halotryptophans,%20halotryptophan%20containing%20tripeptides;%20and%20generation%20of%20a%20new%20to%20nature%20bromo-natural%20product%20and%20its%20diversification%20in%20water&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Corr,%20M%20J&rft.date=2017-03-01&rft.volume=8&rft.issue=3&rft.spage=2039&rft.epage=2046&rft.pages=2039-2046&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/c6sc04423a&rft_dat=%3Cproquest_cross%3E1893552889%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1884112536&rft_id=info:pmid/28451322&rfr_iscdi=true |