Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry

Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry

While DNA-encoded macrocyclic libraries have gained substantial attention and several hit compounds have been identified from DNA-encoded library technology, efficient on-DNA macrocyclic methods are also required to construct DNA-linked libraries with a high degree of cyclization and DNA integrity....

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2024-04, Vol.26 (14), p.2763-2767
Hauptverfasser: Bao, Yandan, Xing, Minyan, Matthew, Naylor, Chen, Xiaohua, Wang, Xuan, Lu, Xiaojie
Format: Artikel
Sprache:eng
Schlagworte:
DNA
peptides
redox reactions
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2767
container_issue 14
container_start_page 2763
container_title Organic letters
container_volume 26
creator Bao, Yandan
Xing, Minyan
Matthew, Naylor
Chen, Xiaohua
Wang, Xuan
Lu, Xiaojie
description While DNA-encoded macrocyclic libraries have gained substantial attention and several hit compounds have been identified from DNA-encoded library technology, efficient on-DNA macrocyclic methods are also required to construct DNA-linked libraries with a high degree of cyclization and DNA integrity. In this paper, we reported a set of on-DNA methodologies, including the use of an OPA-mediated three-component cyclization with native handles of amino acids and photoredox chemistries. These chemistries proceed smoothly under mild conditions in good to excellent conversions, successfully generating novel isoindole, isoindoline, indazolone, and bicyclic scaffolds.
doi_str_mv 10.1021/acs.orglett.3c01817
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3153160069</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3153160069</sourcerecordid><originalsourceid>FETCH-LOGICAL-a378t-5d4054b8116780a5eea9b9e88e3d391ad104a0d4c0ae7945ed12b40d297dab9a3</originalsourceid><addsrcrecordid>eNqFkctOwzAQRS0E4v0FSChLNinjOGnsJQpPqTwWZYkiJx6oIbWL7SCVr8elgSWsPLLOmZHuJeSIwohCRk9l60fWvXQYwoi1QDktN8guLTKWllBkm7_zGHbInvevADT-iG2yw0rGM87ZLnm6la2z7bLt9Kc2L8n53Vk60eYNVfKAi6AV-uRDy2Q6c4hpZecLa9CEpPo2ZNDWJNJEeGaD1Ub1bTSrGc61D255QLaeZefxcHj3yePlxbS6Tif3VzfV2SSVrOQhLVQORd5wSsclB1kgStEI5ByZYoJKRSGXoPIWJJYiL1DRrMlBZaJUshGS7ZOT9d6Fs-89-lDH-y12nTRoe18zWjA6BhiLf9GMM5oJUQiIKFujMSHvHT7XC6fn0i1rCvWqgjpWUA8V1EMF0ToeDvTNHNWv85N5BE7XwMp-tb0zMZo_V34BKxOVtQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2831299590</pqid></control><display><type>article</type><title>Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry</title><source>American Chemical Society Journals</source><creator>Bao, Yandan ; Xing, Minyan ; Matthew, Naylor ; Chen, Xiaohua ; Wang, Xuan ; Lu, Xiaojie</creator><creatorcontrib>Bao, Yandan ; Xing, Minyan ; Matthew, Naylor ; Chen, Xiaohua ; Wang, Xuan ; Lu, Xiaojie</creatorcontrib><description>While DNA-encoded macrocyclic libraries have gained substantial attention and several hit compounds have been identified from DNA-encoded library technology, efficient on-DNA macrocyclic methods are also required to construct DNA-linked libraries with a high degree of cyclization and DNA integrity. In this paper, we reported a set of on-DNA methodologies, including the use of an OPA-mediated three-component cyclization with native handles of amino acids and photoredox chemistries. These chemistries proceed smoothly under mild conditions in good to excellent conversions, successfully generating novel isoindole, isoindoline, indazolone, and bicyclic scaffolds.</description><identifier>ISSN: 1523-7060</identifier><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c01817</identifier><identifier>PMID: 37382883</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>DNA ; peptides ; redox reactions</subject><ispartof>Organic letters, 2024-04, Vol.26 (14), p.2763-2767</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a378t-5d4054b8116780a5eea9b9e88e3d391ad104a0d4c0ae7945ed12b40d297dab9a3</citedby><cites>FETCH-LOGICAL-a378t-5d4054b8116780a5eea9b9e88e3d391ad104a0d4c0ae7945ed12b40d297dab9a3</cites><orcidid>0000-0002-3600-288X ; 0000-0003-3031-7095 ; 0000-0003-4986-0231</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/acs.orglett.3c01817$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c01817$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37382883$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bao, Yandan</creatorcontrib><creatorcontrib>Xing, Minyan</creatorcontrib><creatorcontrib>Matthew, Naylor</creatorcontrib><creatorcontrib>Chen, Xiaohua</creatorcontrib><creatorcontrib>Wang, Xuan</creatorcontrib><creatorcontrib>Lu, Xiaojie</creatorcontrib><title>Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>While DNA-encoded macrocyclic libraries have gained substantial attention and several hit compounds have been identified from DNA-encoded library technology, efficient on-DNA macrocyclic methods are also required to construct DNA-linked libraries with a high degree of cyclization and DNA integrity. In this paper, we reported a set of on-DNA methodologies, including the use of an OPA-mediated three-component cyclization with native handles of amino acids and photoredox chemistries. These chemistries proceed smoothly under mild conditions in good to excellent conversions, successfully generating novel isoindole, isoindoline, indazolone, and bicyclic scaffolds.</description><subject>DNA</subject><subject>peptides</subject><subject>redox reactions</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkctOwzAQRS0E4v0FSChLNinjOGnsJQpPqTwWZYkiJx6oIbWL7SCVr8elgSWsPLLOmZHuJeSIwohCRk9l60fWvXQYwoi1QDktN8guLTKWllBkm7_zGHbInvevADT-iG2yw0rGM87ZLnm6la2z7bLt9Kc2L8n53Vk60eYNVfKAi6AV-uRDy2Q6c4hpZecLa9CEpPo2ZNDWJNJEeGaD1Ub1bTSrGc61D255QLaeZefxcHj3yePlxbS6Tif3VzfV2SSVrOQhLVQORd5wSsclB1kgStEI5ByZYoJKRSGXoPIWJJYiL1DRrMlBZaJUshGS7ZOT9d6Fs-89-lDH-y12nTRoe18zWjA6BhiLf9GMM5oJUQiIKFujMSHvHT7XC6fn0i1rCvWqgjpWUA8V1EMF0ToeDvTNHNWv85N5BE7XwMp-tb0zMZo_V34BKxOVtQ</recordid><startdate>20240412</startdate><enddate>20240412</enddate><creator>Bao, Yandan</creator><creator>Xing, Minyan</creator><creator>Matthew, Naylor</creator><creator>Chen, Xiaohua</creator><creator>Wang, Xuan</creator><creator>Lu, Xiaojie</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-3600-288X</orcidid><orcidid>https://orcid.org/0000-0003-3031-7095</orcidid><orcidid>https://orcid.org/0000-0003-4986-0231</orcidid></search><sort><creationdate>20240412</creationdate><title>Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry</title><author>Bao, Yandan ; Xing, Minyan ; Matthew, Naylor ; Chen, Xiaohua ; Wang, Xuan ; Lu, Xiaojie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a378t-5d4054b8116780a5eea9b9e88e3d391ad104a0d4c0ae7945ed12b40d297dab9a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>DNA</topic><topic>peptides</topic><topic>redox reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bao, Yandan</creatorcontrib><creatorcontrib>Xing, Minyan</creatorcontrib><creatorcontrib>Matthew, Naylor</creatorcontrib><creatorcontrib>Chen, Xiaohua</creatorcontrib><creatorcontrib>Wang, Xuan</creatorcontrib><creatorcontrib>Lu, Xiaojie</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bao, Yandan</au><au>Xing, Minyan</au><au>Matthew, Naylor</au><au>Chen, Xiaohua</au><au>Wang, Xuan</au><au>Lu, Xiaojie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2024-04-12</date><risdate>2024</risdate><volume>26</volume><issue>14</issue><spage>2763</spage><epage>2767</epage><pages>2763-2767</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>While DNA-encoded macrocyclic libraries have gained substantial attention and several hit compounds have been identified from DNA-encoded library technology, efficient on-DNA macrocyclic methods are also required to construct DNA-linked libraries with a high degree of cyclization and DNA integrity. In this paper, we reported a set of on-DNA methodologies, including the use of an OPA-mediated three-component cyclization with native handles of amino acids and photoredox chemistries. These chemistries proceed smoothly under mild conditions in good to excellent conversions, successfully generating novel isoindole, isoindoline, indazolone, and bicyclic scaffolds.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>37382883</pmid><doi>10.1021/acs.orglett.3c01817</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-3600-288X</orcidid><orcidid>https://orcid.org/0000-0003-3031-7095</orcidid><orcidid>https://orcid.org/0000-0003-4986-0231</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2024-04, Vol.26 (14), p.2763-2767
issn 1523-7060
1523-7052
1523-7052
language eng
recordid cdi_proquest_miscellaneous_3153160069
source American Chemical Society Journals
subjects DNA
peptides
redox reactions
title Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T10%3A37%3A53IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Macrocyclizing%20DNA-Linked%20Peptides%20via%20Three-Component%20Cyclization%20and%20Photoinduced%20Chemistry&rft.jtitle=Organic%20letters&rft.au=Bao,%20Yandan&rft.date=2024-04-12&rft.volume=26&rft.issue=14&rft.spage=2763&rft.epage=2767&rft.pages=2763-2767&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c01817&rft_dat=%3Cproquest_cross%3E3153160069%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2831299590&rft_id=info:pmid/37382883&rfr_iscdi=true