A General Strategy to Install Amidine Functional Groups Along the Peptide Backbone
Amidines are a structural surrogate for peptide bonds, yet have received considerably little attention in peptides due to limitations in existing methods to access them. The synthetic strategy developed in this study represents the first robust and general procedure for the introduction of amidines...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2022-12, Vol.144 (49), p.22397-22402 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 22402 |
|---|---|
| container_issue | 49 |
| container_start_page | 22397 |
| container_title | Journal of the American Chemical Society |
| container_volume | 144 |
| creator | O’Brien, Emily A. Sharma, Krishna K. Byerly-Duke, Jacob Camacho, Luis A. VanVeller, Brett |
| description | Amidines are a structural surrogate for peptide bonds, yet have received considerably little attention in peptides due to limitations in existing methods to access them. The synthetic strategy developed in this study represents the first robust and general procedure for the introduction of amidines into the peptide backbone. We exploit and further develop the utility and efficiency of thioimidate protecting groups as a means to side-step reactivity that ultimately renders existing methods unsuitable for the installation of amidines along the main-chain of peptides. This work is significant because it describes a generally applicable path to access unexplored peptide designs and architectures for new therapeutics made possible by the unique properties of amidines. |
| doi_str_mv | 10.1021/jacs.2c09085 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9886086</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2747003575</sourcerecordid><originalsourceid>FETCH-LOGICAL-a417t-3b5b91df53c7c492db8514ef45211ec92aa24f2424c4293dad90c1242877f45a3</originalsourceid><addsrcrecordid>eNptkctLAzEQxoMoWqs3z5KjB7cm2WQfF6EWrYKg-DiHbHa2bt0mNckK_vemtL7A0zDML99Mvg-hI0pGlDB6Nlfaj5gmJSnEFhpQwUgiKMu20YAQwpK8yNI9tO_9PLacFXQX7aUZz0pC-QA9jPEUDDjV4cfgVIDZBw4W3xgfVNfh8aKtWwP4qjc6tNZEbOpsv_R43Fkzw-EF8D0sQ1sDvlD6tbIGDtBOozoPh5s6RM9Xl0-T6-T2bnozGd8mitM8JGklqpLWjUh1rnnJ6qoQlEPDBaMUdMmUYrxhnHHNWZnWqi6JprEv8jxCKh2i87Xusq8WUGsw8QOdXLp2odyHtKqVfyemfZEz-y7LoshIdGWITjYCzr714INctF5D1ykDtveS5TwnJBW5iOjpGtXOeu-g-V5DiVzFIFcxyE0MET_-fdo3_OX7z-rVq7ntXXTW_6_1Cea3kOs</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2747003575</pqid></control><display><type>article</type><title>A General Strategy to Install Amidine Functional Groups Along the Peptide Backbone</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>O’Brien, Emily A. ; Sharma, Krishna K. ; Byerly-Duke, Jacob ; Camacho, Luis A. ; VanVeller, Brett</creator><creatorcontrib>O’Brien, Emily A. ; Sharma, Krishna K. ; Byerly-Duke, Jacob ; Camacho, Luis A. ; VanVeller, Brett</creatorcontrib><description>Amidines are a structural surrogate for peptide bonds, yet have received considerably little attention in peptides due to limitations in existing methods to access them. The synthetic strategy developed in this study represents the first robust and general procedure for the introduction of amidines into the peptide backbone. We exploit and further develop the utility and efficiency of thioimidate protecting groups as a means to side-step reactivity that ultimately renders existing methods unsuitable for the installation of amidines along the main-chain of peptides. This work is significant because it describes a generally applicable path to access unexplored peptide designs and architectures for new therapeutics made possible by the unique properties of amidines.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.2c09085</identifier><identifier>PMID: 36469014</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amidines - chemistry ; Peptides - chemistry</subject><ispartof>Journal of the American Chemical Society, 2022-12, Vol.144 (49), p.22397-22402</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a417t-3b5b91df53c7c492db8514ef45211ec92aa24f2424c4293dad90c1242877f45a3</citedby><cites>FETCH-LOGICAL-a417t-3b5b91df53c7c492db8514ef45211ec92aa24f2424c4293dad90c1242877f45a3</cites><orcidid>0000-0002-3792-0308 ; 0000-0003-4927-745X ; 0000-0001-6329-1966</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/jacs.2c09085$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.2c09085$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36469014$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>O’Brien, Emily A.</creatorcontrib><creatorcontrib>Sharma, Krishna K.</creatorcontrib><creatorcontrib>Byerly-Duke, Jacob</creatorcontrib><creatorcontrib>Camacho, Luis A.</creatorcontrib><creatorcontrib>VanVeller, Brett</creatorcontrib><title>A General Strategy to Install Amidine Functional Groups Along the Peptide Backbone</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Amidines are a structural surrogate for peptide bonds, yet have received considerably little attention in peptides due to limitations in existing methods to access them. The synthetic strategy developed in this study represents the first robust and general procedure for the introduction of amidines into the peptide backbone. We exploit and further develop the utility and efficiency of thioimidate protecting groups as a means to side-step reactivity that ultimately renders existing methods unsuitable for the installation of amidines along the main-chain of peptides. This work is significant because it describes a generally applicable path to access unexplored peptide designs and architectures for new therapeutics made possible by the unique properties of amidines.</description><subject>Amidines - chemistry</subject><subject>Peptides - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkctLAzEQxoMoWqs3z5KjB7cm2WQfF6EWrYKg-DiHbHa2bt0mNckK_vemtL7A0zDML99Mvg-hI0pGlDB6Nlfaj5gmJSnEFhpQwUgiKMu20YAQwpK8yNI9tO_9PLacFXQX7aUZz0pC-QA9jPEUDDjV4cfgVIDZBw4W3xgfVNfh8aKtWwP4qjc6tNZEbOpsv_R43Fkzw-EF8D0sQ1sDvlD6tbIGDtBOozoPh5s6RM9Xl0-T6-T2bnozGd8mitM8JGklqpLWjUh1rnnJ6qoQlEPDBaMUdMmUYrxhnHHNWZnWqi6JprEv8jxCKh2i87Xusq8WUGsw8QOdXLp2odyHtKqVfyemfZEz-y7LoshIdGWITjYCzr714INctF5D1ykDtveS5TwnJBW5iOjpGtXOeu-g-V5DiVzFIFcxyE0MET_-fdo3_OX7z-rVq7ntXXTW_6_1Cea3kOs</recordid><startdate>20221214</startdate><enddate>20221214</enddate><creator>O’Brien, Emily A.</creator><creator>Sharma, Krishna K.</creator><creator>Byerly-Duke, Jacob</creator><creator>Camacho, Luis A.</creator><creator>VanVeller, Brett</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><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3792-0308</orcidid><orcidid>https://orcid.org/0000-0003-4927-745X</orcidid><orcidid>https://orcid.org/0000-0001-6329-1966</orcidid></search><sort><creationdate>20221214</creationdate><title>A General Strategy to Install Amidine Functional Groups Along the Peptide Backbone</title><author>O’Brien, Emily A. ; Sharma, Krishna K. ; Byerly-Duke, Jacob ; Camacho, Luis A. ; VanVeller, Brett</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a417t-3b5b91df53c7c492db8514ef45211ec92aa24f2424c4293dad90c1242877f45a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Amidines - chemistry</topic><topic>Peptides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>O’Brien, Emily A.</creatorcontrib><creatorcontrib>Sharma, Krishna K.</creatorcontrib><creatorcontrib>Byerly-Duke, Jacob</creatorcontrib><creatorcontrib>Camacho, Luis A.</creatorcontrib><creatorcontrib>VanVeller, Brett</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>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>O’Brien, Emily A.</au><au>Sharma, Krishna K.</au><au>Byerly-Duke, Jacob</au><au>Camacho, Luis A.</au><au>VanVeller, Brett</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A General Strategy to Install Amidine Functional Groups Along the Peptide Backbone</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2022-12-14</date><risdate>2022</risdate><volume>144</volume><issue>49</issue><spage>22397</spage><epage>22402</epage><pages>22397-22402</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Amidines are a structural surrogate for peptide bonds, yet have received considerably little attention in peptides due to limitations in existing methods to access them. The synthetic strategy developed in this study represents the first robust and general procedure for the introduction of amidines into the peptide backbone. We exploit and further develop the utility and efficiency of thioimidate protecting groups as a means to side-step reactivity that ultimately renders existing methods unsuitable for the installation of amidines along the main-chain of peptides. This work is significant because it describes a generally applicable path to access unexplored peptide designs and architectures for new therapeutics made possible by the unique properties of amidines.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36469014</pmid><doi>10.1021/jacs.2c09085</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3792-0308</orcidid><orcidid>https://orcid.org/0000-0003-4927-745X</orcidid><orcidid>https://orcid.org/0000-0001-6329-1966</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2022-12, Vol.144 (49), p.22397-22402 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9886086 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Amidines - chemistry Peptides - chemistry |
| title | A General Strategy to Install Amidine Functional Groups Along the Peptide Backbone |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T15%3A47%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20General%20Strategy%20to%20Install%20Amidine%20Functional%20Groups%20Along%20the%20Peptide%20Backbone&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=O%E2%80%99Brien,%20Emily%20A.&rft.date=2022-12-14&rft.volume=144&rft.issue=49&rft.spage=22397&rft.epage=22402&rft.pages=22397-22402&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.2c09085&rft_dat=%3Cproquest_pubme%3E2747003575%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2747003575&rft_id=info:pmid/36469014&rfr_iscdi=true |