One-Pot Photochemical Ring-Opening/Cleavage Approach for the Synthesis and Decoding of Cyclic Peptide Libraries
A novel dual ring-opening/cleavage strategy to determine the sequence of cyclic peptides from one bead, one compound libraries is described. The approach uses a photolabile residue within the macrocycle and as a linker to allow a simultaneous ring opening and cleavage from the beads upon UV irradiat...
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| Veröffentlicht in: | Organic letters 2016-03, Vol.18 (5), p.1174-1177 |
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| container_end_page | 1177 |
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| container_issue | 5 |
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| container_title | Organic letters |
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| creator | Liang, Xinxia Vézina-Dawod, Simon Bédard, François Porte, Karine Biron, Eric |
| description | A novel dual ring-opening/cleavage strategy to determine the sequence of cyclic peptides from one bead, one compound libraries is described. The approach uses a photolabile residue within the macrocycle and as a linker to allow a simultaneous ring opening and cleavage from the beads upon UV irradiation and provide linearized molecules. Cyclic peptides of five to nine residues were synthesized and the generated linear peptides successfully sequenced by tandem mass spectrometry. |
| doi_str_mv | 10.1021/acs.orglett.6b00296 |
| format | Article |
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Cyclic peptides of five to nine residues were synthesized and the generated linear peptides successfully sequenced by tandem mass spectrometry.</description><subject>Molecular Structure</subject><subject>Peptide Library</subject><subject>Peptides - chemical synthesis</subject><subject>Peptides - chemistry</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Photochemical Processes</subject><subject>Tandem Mass Spectrometry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kElrwzAQhUVpadLlFxSKjr040RLJ9jGkKwQSupyNLI0TBcdyJbuQf1-FpDn29IbhvVk-hO4oGVHC6FjpMHJ-VUPXjWRJCMvlGRpSwXiSEsHOT7UkA3QVwoYQGjv5JRowmdNJysQQuUUDydJ1eLl2ndNr2Fqtavxum1WyaKGJOp7VoH7UCvC0bb1Teo0r53G3Bvyxa6IEG7BqDH4E7UwMYFfh2U7XVuMltJ01gOe29MpbCDfoolJ1gNujXqOv56fP2WsyX7y8zabzRPGJ6BJVSWC0TA1jKRVZxQFKSUpqJPBMTgRjCsiEVlwANURAbiDXWSmMyURZCc6v0cNhbrz4u4fQFVsbNNS1asD1oaBpSrKUEyajlR-s2rsQPFRF6-1W-V1BSbEnXUTSxZF0cSQdU_fHBX25BXPK_KGNhvHBsE9vXO-b-O-_I38BYVON8g</recordid><startdate>20160304</startdate><enddate>20160304</enddate><creator>Liang, Xinxia</creator><creator>Vézina-Dawod, Simon</creator><creator>Bédard, François</creator><creator>Porte, Karine</creator><creator>Biron, Eric</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></search><sort><creationdate>20160304</creationdate><title>One-Pot Photochemical Ring-Opening/Cleavage Approach for the Synthesis and Decoding of Cyclic Peptide Libraries</title><author>Liang, Xinxia ; Vézina-Dawod, Simon ; Bédard, François ; Porte, Karine ; Biron, Eric</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-af6e21b7d227158f3eeb60b1d6e3864522ae041f35e1d05e9de9c8b5dd85bf533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Molecular Structure</topic><topic>Peptide Library</topic><topic>Peptides - chemical synthesis</topic><topic>Peptides - chemistry</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Photochemical Processes</topic><topic>Tandem Mass Spectrometry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liang, Xinxia</creatorcontrib><creatorcontrib>Vézina-Dawod, Simon</creatorcontrib><creatorcontrib>Bédard, François</creatorcontrib><creatorcontrib>Porte, Karine</creatorcontrib><creatorcontrib>Biron, Eric</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liang, Xinxia</au><au>Vézina-Dawod, Simon</au><au>Bédard, François</au><au>Porte, Karine</au><au>Biron, Eric</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-Pot Photochemical Ring-Opening/Cleavage Approach for the Synthesis and Decoding of Cyclic Peptide Libraries</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2016-03, Vol.18 (5), p.1174-1177 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Molecular Structure Peptide Library Peptides - chemical synthesis Peptides - chemistry Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Photochemical Processes Tandem Mass Spectrometry |
| title | One-Pot Photochemical Ring-Opening/Cleavage Approach for the Synthesis and Decoding of Cyclic Peptide Libraries |
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