Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis
A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on...
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| Veröffentlicht in: | ACS catalysis 2020-04, Vol.10 (7), p.4280-4289 |
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| container_title | ACS catalysis |
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| creator | Hollanders, Karlijn Renders, Evelien Gadais, Charlène Masullo, Dario Van Raemdonck, Laurent Wybon, Clarence C. D Martin, Charlotte Herrebout, Wouter A Maes, Bert U. W Ballet, Steven |
| description | A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide. |
| doi_str_mv | 10.1021/acscatal.9b05074 |
| format | Article |
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D ; Martin, Charlotte ; Herrebout, Wouter A ; Maes, Bert U. W ; Ballet, Steven</creator><creatorcontrib>Hollanders, Karlijn ; Renders, Evelien ; Gadais, Charlène ; Masullo, Dario ; Van Raemdonck, Laurent ; Wybon, Clarence C. D ; Martin, Charlotte ; Herrebout, Wouter A ; Maes, Bert U. W ; Ballet, Steven</creatorcontrib><description>A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.</description><identifier>ISSN: 2155-5435</identifier><identifier>EISSN: 2155-5435</identifier><identifier>DOI: 10.1021/acscatal.9b05074</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>ACS catalysis, 2020-04, Vol.10 (7), p.4280-4289</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a346t-6aae83ed96571b6defb3306286080f402c194a05728c315ad9adbeb6e88a6d1b3</citedby><cites>FETCH-LOGICAL-a346t-6aae83ed96571b6defb3306286080f402c194a05728c315ad9adbeb6e88a6d1b3</cites><orcidid>0000-0001-6236-609X ; 0000-0003-0431-7606 ; 0000-0003-4123-1641 ; 0000-0002-3167-8944 ; 0000-0002-5212-676X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acscatal.9b05074$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acscatal.9b05074$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids></links><search><creatorcontrib>Hollanders, Karlijn</creatorcontrib><creatorcontrib>Renders, Evelien</creatorcontrib><creatorcontrib>Gadais, Charlène</creatorcontrib><creatorcontrib>Masullo, Dario</creatorcontrib><creatorcontrib>Van Raemdonck, Laurent</creatorcontrib><creatorcontrib>Wybon, Clarence C. D</creatorcontrib><creatorcontrib>Martin, Charlotte</creatorcontrib><creatorcontrib>Herrebout, Wouter A</creatorcontrib><creatorcontrib>Maes, Bert U. W</creatorcontrib><creatorcontrib>Ballet, Steven</creatorcontrib><title>Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis</title><title>ACS catalysis</title><addtitle>ACS Catal</addtitle><description>A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.</description><issn>2155-5435</issn><issn>2155-5435</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kMFOwzAMQCMEEtPYnWM_gA6nadL0iMZgSBMgMS5cKjdxRaYtnZJwGF9Ppw2JC77Ysv0s6zF2zWHKoeC3aKLBhJtp3YKEqjxjo4JLmctSyPM_9SWbxLiGIUqpdAUjNv_w-eyA7r_JZs_O9Ml5TJTfu0AmDb1VQB9x6ywm1_uYOZ-90i45S9nb3qdPii5esYsON5Empzxm7w_z1WyRL18en2Z3yxxFqVKuEEkLsrWSFW-Vpa4VAlShFWjoSigMr0sEWRXaCC7R1mhbahVpjcryVowZHO-a0McYqGt2wW0x7BsOzcFE82uiOZkYkJsjMkyadf8V_PDg_-s_Q_Rizg</recordid><startdate>20200403</startdate><enddate>20200403</enddate><creator>Hollanders, Karlijn</creator><creator>Renders, Evelien</creator><creator>Gadais, Charlène</creator><creator>Masullo, Dario</creator><creator>Van Raemdonck, Laurent</creator><creator>Wybon, Clarence C. D</creator><creator>Martin, Charlotte</creator><creator>Herrebout, Wouter A</creator><creator>Maes, Bert U. W</creator><creator>Ballet, Steven</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6236-609X</orcidid><orcidid>https://orcid.org/0000-0003-0431-7606</orcidid><orcidid>https://orcid.org/0000-0003-4123-1641</orcidid><orcidid>https://orcid.org/0000-0002-3167-8944</orcidid><orcidid>https://orcid.org/0000-0002-5212-676X</orcidid></search><sort><creationdate>20200403</creationdate><title>Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis</title><author>Hollanders, Karlijn ; Renders, Evelien ; Gadais, Charlène ; Masullo, Dario ; Van Raemdonck, Laurent ; Wybon, Clarence C. D ; Martin, Charlotte ; Herrebout, Wouter A ; Maes, Bert U. W ; Ballet, Steven</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a346t-6aae83ed96571b6defb3306286080f402c194a05728c315ad9adbeb6e88a6d1b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hollanders, Karlijn</creatorcontrib><creatorcontrib>Renders, Evelien</creatorcontrib><creatorcontrib>Gadais, Charlène</creatorcontrib><creatorcontrib>Masullo, Dario</creatorcontrib><creatorcontrib>Van Raemdonck, Laurent</creatorcontrib><creatorcontrib>Wybon, Clarence C. D</creatorcontrib><creatorcontrib>Martin, Charlotte</creatorcontrib><creatorcontrib>Herrebout, Wouter A</creatorcontrib><creatorcontrib>Maes, Bert U. W</creatorcontrib><creatorcontrib>Ballet, Steven</creatorcontrib><collection>CrossRef</collection><jtitle>ACS catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hollanders, Karlijn</au><au>Renders, Evelien</au><au>Gadais, Charlène</au><au>Masullo, Dario</au><au>Van Raemdonck, Laurent</au><au>Wybon, Clarence C. D</au><au>Martin, Charlotte</au><au>Herrebout, Wouter A</au><au>Maes, Bert U. W</au><au>Ballet, Steven</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis</atitle><jtitle>ACS catalysis</jtitle><addtitle>ACS Catal</addtitle><date>2020-04-03</date><risdate>2020</risdate><volume>10</volume><issue>7</issue><spage>4280</spage><epage>4289</epage><pages>4280-4289</pages><issn>2155-5435</issn><eissn>2155-5435</eissn><abstract>A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.</abstract><pub>American Chemical Society</pub><doi>10.1021/acscatal.9b05074</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-6236-609X</orcidid><orcidid>https://orcid.org/0000-0003-0431-7606</orcidid><orcidid>https://orcid.org/0000-0003-4123-1641</orcidid><orcidid>https://orcid.org/0000-0002-3167-8944</orcidid><orcidid>https://orcid.org/0000-0002-5212-676X</orcidid></addata></record> |
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| title | Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis |
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