Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker
[Display omitted] A head-to-tail macrocyclization protocol for the preparation of cysteine-free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-mediated activation under acid...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2018-05, Vol.28 (8), p.1283-1286 |
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| container_issue | 8 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 28 |
| creator | Ohara, Takumi Kaneda, Masato Saito, Tomo Fujii, Nobutaka Ohno, Hiroaki Oishi, Shinya |
| description | [Display omitted]
A head-to-tail macrocyclization protocol for the preparation of cysteine-free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-mediated activation under acidic conditions toward N-acyl benzotriazole as the active ester species. The subsequent cyclization smoothly proceeded by neutralization in the presence of additives such as 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) to afford the expected cyclic pentapeptide, a CXCR4 antagonist. The cyclization efficiencies were dependent on the precursor open-chain sequence. The application of this step-wise activation-cyclization protocol to microflow reaction systems is also described. |
| doi_str_mv | 10.1016/j.bmcl.2018.03.027 |
| format | Article |
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A head-to-tail macrocyclization protocol for the preparation of cysteine-free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-mediated activation under acidic conditions toward N-acyl benzotriazole as the active ester species. The subsequent cyclization smoothly proceeded by neutralization in the presence of additives such as 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) to afford the expected cyclic pentapeptide, a CXCR4 antagonist. The cyclization efficiencies were dependent on the precursor open-chain sequence. The application of this step-wise activation-cyclization protocol to microflow reaction systems is also described.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2018.03.027</identifier><identifier>PMID: 29580681</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amino Acid Sequence ; Anilides - chemical synthesis ; Anilides - chemistry ; Aza Compounds - chemistry ; Chemokine ; CXCR4 antagonist ; Cyclic peptide ; Cyclization ; Macrocyclization ; Microflow reaction ; Peptides - chemistry ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; Triazoles - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-05, Vol.28 (8), p.1283-1286</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c422t-4c080796e8f477945cf5e62d9d7ba90cfa35f657e811a837e0d29b3164cf11233</citedby><cites>FETCH-LOGICAL-c422t-4c080796e8f477945cf5e62d9d7ba90cfa35f657e811a837e0d29b3164cf11233</cites><orcidid>0000-0002-2833-2539 ; 0000-0002-3246-4809</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2018.03.027$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29580681$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ohara, Takumi</creatorcontrib><creatorcontrib>Kaneda, Masato</creatorcontrib><creatorcontrib>Saito, Tomo</creatorcontrib><creatorcontrib>Fujii, Nobutaka</creatorcontrib><creatorcontrib>Ohno, Hiroaki</creatorcontrib><creatorcontrib>Oishi, Shinya</creatorcontrib><title>Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A head-to-tail macrocyclization protocol for the preparation of cysteine-free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-mediated activation under acidic conditions toward N-acyl benzotriazole as the active ester species. The subsequent cyclization smoothly proceeded by neutralization in the presence of additives such as 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) to afford the expected cyclic pentapeptide, a CXCR4 antagonist. The cyclization efficiencies were dependent on the precursor open-chain sequence. The application of this step-wise activation-cyclization protocol to microflow reaction systems is also described.</description><subject>Amino Acid Sequence</subject><subject>Anilides - chemical synthesis</subject><subject>Anilides - chemistry</subject><subject>Aza Compounds - chemistry</subject><subject>Chemokine</subject><subject>CXCR4 antagonist</subject><subject>Cyclic peptide</subject><subject>Cyclization</subject><subject>Macrocyclization</subject><subject>Microflow reaction</subject><subject>Peptides - chemistry</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Triazoles - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LAzEURYMoWqt_wIXM0k3Gl0wmk4AbEbWC4EbFXUgzL5I6HzWZCvXXO6XVpau3eOdeuIeQMwY5AyYvF_m8dU3Ogakcihx4tUcmTEhBCwHlPpmAlkCVFm9H5DilBQATIMQhOeK6VCAVm5DXGdqaDj0dbGiy1rrYu7VrwrcdQt9lvc_cOg0YOqQ-ImZLXA6hxpStUujeMzsi1Lah620XmvGRNaH7wHhCDrxtEp7u7pS83N0-38zo49P9w831I3WC84EKBwoqLVF5UVValM6XKHmt62puNThvi9LLskLFmFVFhVBzPS-YFM4zxotiSi62vcvYf64wDaYNyWHT2A77VTKjGw0CQG5QvkXHiSlF9GYZQ2vj2jAwG59mYTY-NxlloDCjzzF0vutfzVus_yK_AkfgagvguPIrYDTJBewc1iGiG0zdh__6fwBDWoa3</recordid><startdate>20180501</startdate><enddate>20180501</enddate><creator>Ohara, Takumi</creator><creator>Kaneda, Masato</creator><creator>Saito, Tomo</creator><creator>Fujii, Nobutaka</creator><creator>Ohno, Hiroaki</creator><creator>Oishi, Shinya</creator><general>Elsevier Ltd</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><orcidid>https://orcid.org/0000-0002-2833-2539</orcidid><orcidid>https://orcid.org/0000-0002-3246-4809</orcidid></search><sort><creationdate>20180501</creationdate><title>Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker</title><author>Ohara, Takumi ; Kaneda, Masato ; Saito, Tomo ; Fujii, Nobutaka ; Ohno, Hiroaki ; Oishi, Shinya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c422t-4c080796e8f477945cf5e62d9d7ba90cfa35f657e811a837e0d29b3164cf11233</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Amino Acid Sequence</topic><topic>Anilides - chemical synthesis</topic><topic>Anilides - chemistry</topic><topic>Aza Compounds - chemistry</topic><topic>Chemokine</topic><topic>CXCR4 antagonist</topic><topic>Cyclic peptide</topic><topic>Cyclization</topic><topic>Macrocyclization</topic><topic>Microflow reaction</topic><topic>Peptides - chemistry</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Triazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ohara, Takumi</creatorcontrib><creatorcontrib>Kaneda, Masato</creatorcontrib><creatorcontrib>Saito, Tomo</creatorcontrib><creatorcontrib>Fujii, Nobutaka</creatorcontrib><creatorcontrib>Ohno, Hiroaki</creatorcontrib><creatorcontrib>Oishi, Shinya</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ohara, Takumi</au><au>Kaneda, Masato</au><au>Saito, Tomo</au><au>Fujii, Nobutaka</au><au>Ohno, Hiroaki</au><au>Oishi, Shinya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-05-01</date><risdate>2018</risdate><volume>28</volume><issue>8</issue><spage>1283</spage><epage>1286</epage><pages>1283-1286</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A head-to-tail macrocyclization protocol for the preparation of cysteine-free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-mediated activation under acidic conditions toward N-acyl benzotriazole as the active ester species. The subsequent cyclization smoothly proceeded by neutralization in the presence of additives such as 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) to afford the expected cyclic pentapeptide, a CXCR4 antagonist. The cyclization efficiencies were dependent on the precursor open-chain sequence. The application of this step-wise activation-cyclization protocol to microflow reaction systems is also described.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29580681</pmid><doi>10.1016/j.bmcl.2018.03.027</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-2833-2539</orcidid><orcidid>https://orcid.org/0000-0002-3246-4809</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2018-05, Vol.28 (8), p.1283-1286 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2019040063 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Amino Acid Sequence Anilides - chemical synthesis Anilides - chemistry Aza Compounds - chemistry Chemokine CXCR4 antagonist Cyclic peptide Cyclization Macrocyclization Microflow reaction Peptides - chemistry Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Triazoles - chemistry |
| title | Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker |
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