Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation

Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes. Solution-...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2016-09, Vol.14 (35), p.8367-8375
Hauptverfasser: Pirrung, Michael C, Zhang, Fa, Ambadi, Sudhakar, Gangadhara Rao, Y
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 8375
container_issue 35
container_start_page 8367
container_title Organic & biomolecular chemistry
container_volume 14
creator Pirrung, Michael C
Zhang, Fa
Ambadi, Sudhakar
Gangadhara Rao, Y
description Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes. Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved.
doi_str_mv 10.1039/c6ob01233g
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1827890697</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1827890697</sourcerecordid><originalsourceid>FETCH-LOGICAL-c433t-cb1009c5b67f1e0ad9b06093f976c721363ac3f0d7545968314ec36807f222cc3</originalsourceid><addsrcrecordid>eNqNkkFvFDEMhSMEou3CpfeiHFHVLU48k2wulWDVFqSiXso5ymSSbtqZyZBkkPrvO7DLAjdOtvU-WbafCTlmcM4A1QcrYgOMI96_IIesknIJNaqX-5zDATnK-QGAKSmq1-SAyxpRcTgkj3exmI7mp6FsXA6ZRk-967qpmD60Lp_RLoxxdGOZKzqmWJzJsXc0DJvQhBJTPqdfY3I0T7mYMJimm7kd38ShpT6m3pQQhzfklTdddm93cUG-XV3erT8vb26vv6w_3ixthViWtmEAytaNkJ45MK1qQIBCPw9vJWco0Fj00Mq6qpVYIaucRbEC6Tnn1uKCXGz7jlPTu9a6oSTT6TGF3qQnHU3Q_ypD2Oj7-EPXCAjzSRfk_a5Bit8nl4vuQ7bzVczg4pQ1W3G5UiCU_A-UCYFQM5zR0y1qU8w5Ob-fiIH-aaRei9tPv4y8nuF3f--wR387NwMnWyBlu1f_fAI-A5bypME</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1816630513</pqid></control><display><type>article</type><title>Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Pirrung, Michael C ; Zhang, Fa ; Ambadi, Sudhakar ; Gangadhara Rao, Y</creator><creatorcontrib>Pirrung, Michael C ; Zhang, Fa ; Ambadi, Sudhakar ; Gangadhara Rao, Y</creatorcontrib><description>Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes. Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c6ob01233g</identifier><identifier>PMID: 27533920</identifier><language>eng</language><publisher>England</publisher><subject>Biological Products - chemistry ; Chemistry Techniques, Synthetic - methods ; Lipopeptides - chemical synthesis ; Molecular Structure ; Oligopeptides - chemical synthesis ; Proteasome Inhibitors - chemical synthesis ; Solutions - chemistry</subject><ispartof>Organic &amp; biomolecular chemistry, 2016-09, Vol.14 (35), p.8367-8375</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c433t-cb1009c5b67f1e0ad9b06093f976c721363ac3f0d7545968314ec36807f222cc3</citedby><cites>FETCH-LOGICAL-c433t-cb1009c5b67f1e0ad9b06093f976c721363ac3f0d7545968314ec36807f222cc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27533920$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pirrung, Michael C</creatorcontrib><creatorcontrib>Zhang, Fa</creatorcontrib><creatorcontrib>Ambadi, Sudhakar</creatorcontrib><creatorcontrib>Gangadhara Rao, Y</creatorcontrib><title>Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes. Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved.</description><subject>Biological Products - chemistry</subject><subject>Chemistry Techniques, Synthetic - methods</subject><subject>Lipopeptides - chemical synthesis</subject><subject>Molecular Structure</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Proteasome Inhibitors - chemical synthesis</subject><subject>Solutions - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkkFvFDEMhSMEou3CpfeiHFHVLU48k2wulWDVFqSiXso5ymSSbtqZyZBkkPrvO7DLAjdOtvU-WbafCTlmcM4A1QcrYgOMI96_IIesknIJNaqX-5zDATnK-QGAKSmq1-SAyxpRcTgkj3exmI7mp6FsXA6ZRk-967qpmD60Lp_RLoxxdGOZKzqmWJzJsXc0DJvQhBJTPqdfY3I0T7mYMJimm7kd38ShpT6m3pQQhzfklTdddm93cUG-XV3erT8vb26vv6w_3ixthViWtmEAytaNkJ45MK1qQIBCPw9vJWco0Fj00Mq6qpVYIaucRbEC6Tnn1uKCXGz7jlPTu9a6oSTT6TGF3qQnHU3Q_ypD2Oj7-EPXCAjzSRfk_a5Bit8nl4vuQ7bzVczg4pQ1W3G5UiCU_A-UCYFQM5zR0y1qU8w5Ob-fiIH-aaRei9tPv4y8nuF3f--wR387NwMnWyBlu1f_fAI-A5bypME</recordid><startdate>20160921</startdate><enddate>20160921</enddate><creator>Pirrung, Michael C</creator><creator>Zhang, Fa</creator><creator>Ambadi, Sudhakar</creator><creator>Gangadhara Rao, Y</creator><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20160921</creationdate><title>Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation</title><author>Pirrung, Michael C ; Zhang, Fa ; Ambadi, Sudhakar ; Gangadhara Rao, Y</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c433t-cb1009c5b67f1e0ad9b06093f976c721363ac3f0d7545968314ec36807f222cc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Biological Products - chemistry</topic><topic>Chemistry Techniques, Synthetic - methods</topic><topic>Lipopeptides - chemical synthesis</topic><topic>Molecular Structure</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Proteasome Inhibitors - chemical synthesis</topic><topic>Solutions - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pirrung, Michael C</creatorcontrib><creatorcontrib>Zhang, Fa</creatorcontrib><creatorcontrib>Ambadi, Sudhakar</creatorcontrib><creatorcontrib>Gangadhara Rao, Y</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pirrung, Michael C</au><au>Zhang, Fa</au><au>Ambadi, Sudhakar</au><au>Gangadhara Rao, Y</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2016-09-21</date><risdate>2016</risdate><volume>14</volume><issue>35</issue><spage>8367</spage><epage>8375</epage><pages>8367-8375</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes. Solution-phase syntheses of three bioactive natural products of mixed polypeptidepolyketide biogenesis, fellutamides A, B, and C, have been achieved.</abstract><cop>England</cop><pmid>27533920</pmid><doi>10.1039/c6ob01233g</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2016-09, Vol.14 (35), p.8367-8375
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_1827890697
source MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection
subjects Biological Products - chemistry
Chemistry Techniques, Synthetic - methods
Lipopeptides - chemical synthesis
Molecular Structure
Oligopeptides - chemical synthesis
Proteasome Inhibitors - chemical synthesis
Solutions - chemistry
title Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T14%3A05%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=Total%20synthesis%20of%20fellutamides,%20lipopeptide%20proteasome%20inhibitors.%20More%20sustainable%20peptide%20bond%20formation&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Pirrung,%20Michael%20C&rft.date=2016-09-21&rft.volume=14&rft.issue=35&rft.spage=8367&rft.epage=8375&rft.pages=8367-8375&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c6ob01233g&rft_dat=%3Cproquest_cross%3E1827890697%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=1816630513&rft_id=info:pmid/27533920&rfr_iscdi=true