Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction
Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2019-08, Vol.55 (71), p.1567-157 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Yamaguchi, Akitake Kaldas, Sherif J Appavoo, Solomon D Diaz, Diego B Yudin, Andrei K |
| description | Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.
Synthesis and the structural analysis of conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction are reported. |
| doi_str_mv | 10.1039/c9cc05934b |
| format | Article |
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Synthesis and the structural analysis of conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction are reported.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc05934b</identifier><identifier>PMID: 31417998</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes - chemistry ; Amides - chemistry ; Amines - chemistry ; Aziridines - chemistry ; Boronic Acids - chemistry ; Crystallography ; Cyclization ; Hydrogen bonds ; Macrocyclic Compounds - chemical synthesis ; Peptides ; Peptides, Cyclic - chemical synthesis</subject><ispartof>Chemical communications (Cambridge, England), 2019-08, Vol.55 (71), p.1567-157</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-ee87d24e4ad4e42bc9aff64cbe22c1139f5e5ec455182356b39d01dc243fc9a63</citedby><cites>FETCH-LOGICAL-c337t-ee87d24e4ad4e42bc9aff64cbe22c1139f5e5ec455182356b39d01dc243fc9a63</cites><orcidid>0000-0001-8293-1084 ; 0000-0003-3170-9103 ; 0000-0003-2497-1963</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31417998$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamaguchi, Akitake</creatorcontrib><creatorcontrib>Kaldas, Sherif J</creatorcontrib><creatorcontrib>Appavoo, Solomon D</creatorcontrib><creatorcontrib>Diaz, Diego B</creatorcontrib><creatorcontrib>Yudin, Andrei K</creatorcontrib><title>Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.
Synthesis and the structural analysis of conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction are reported.</description><subject>Aldehydes - chemistry</subject><subject>Amides - chemistry</subject><subject>Amines - chemistry</subject><subject>Aziridines - chemistry</subject><subject>Boronic Acids - chemistry</subject><subject>Crystallography</subject><subject>Cyclization</subject><subject>Hydrogen bonds</subject><subject>Macrocyclic Compounds - chemical synthesis</subject><subject>Peptides</subject><subject>Peptides, Cyclic - chemical synthesis</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0c9LwzAUB_AgitPpxbsS8CJCtfm1Nkct_oKJHhS8lfT11XW0zUzaw_57MzcnmEMSeB9eeN8QcsLiKxYLfQ0aIFZayGKHHDAxkZGS6cfu6q50lAipRuTQ-3kcFlPpPhkJJlmidXpA8sx2lXWt6WvbmaZZUt-bokG6wEVfl0hbA87CEhr01HiPbSiWdPB190n7GdJX7I2vPS2ss52Nnk3X1TCjDg2sWh6Rvco0Ho8355i839-9ZY_R9OXhKbuZRiBE0keIaVJyidKUYeMFaFNVEwkFcg6MCV0pVAhSKZZyoSaF0GXMSuBSVMFOxJhcrPsunP0a0Pd5W3vApjEd2sHnnCeKKxFrEej5Pzq3gwvDr1TKw2shnKAu1yqM773DKl-4ujVumbM4X8WeZzrLfmK_Dfhs03IoWiy39DfnAE7XwHnYVv_-TXwD0BqIPQ</recordid><startdate>20190829</startdate><enddate>20190829</enddate><creator>Yamaguchi, Akitake</creator><creator>Kaldas, Sherif J</creator><creator>Appavoo, Solomon D</creator><creator>Diaz, Diego B</creator><creator>Yudin, Andrei K</creator><general>Royal Society of Chemistry</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8293-1084</orcidid><orcidid>https://orcid.org/0000-0003-3170-9103</orcidid><orcidid>https://orcid.org/0000-0003-2497-1963</orcidid></search><sort><creationdate>20190829</creationdate><title>Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction</title><author>Yamaguchi, Akitake ; Kaldas, Sherif J ; Appavoo, Solomon D ; Diaz, Diego B ; Yudin, Andrei K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-ee87d24e4ad4e42bc9aff64cbe22c1139f5e5ec455182356b39d01dc243fc9a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aldehydes - chemistry</topic><topic>Amides - chemistry</topic><topic>Amines - chemistry</topic><topic>Aziridines - chemistry</topic><topic>Boronic Acids - chemistry</topic><topic>Crystallography</topic><topic>Cyclization</topic><topic>Hydrogen bonds</topic><topic>Macrocyclic Compounds - chemical synthesis</topic><topic>Peptides</topic><topic>Peptides, Cyclic - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamaguchi, Akitake</creatorcontrib><creatorcontrib>Kaldas, Sherif J</creatorcontrib><creatorcontrib>Appavoo, Solomon D</creatorcontrib><creatorcontrib>Diaz, Diego B</creatorcontrib><creatorcontrib>Yudin, Andrei K</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamaguchi, Akitake</au><au>Kaldas, Sherif J</au><au>Appavoo, Solomon D</au><au>Diaz, Diego B</au><au>Yudin, Andrei K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2019-08-29</date><risdate>2019</risdate><volume>55</volume><issue>71</issue><spage>1567</spage><epage>157</epage><pages>1567-157</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.
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| ispartof | Chemical communications (Cambridge, England), 2019-08, Vol.55 (71), p.1567-157 |
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| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes - chemistry Amides - chemistry Amines - chemistry Aziridines - chemistry Boronic Acids - chemistry Crystallography Cyclization Hydrogen bonds Macrocyclic Compounds - chemical synthesis Peptides Peptides, Cyclic - chemical synthesis |
| title | Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction |
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