Loading…
Orthogonal End Labelling of Oligonucleotides through Dual Incorporation of Click‐Reactive NTP Analogues
Post‐synthetic modification of nucleic acid structures with clickable functionality is a versatile tool that facilitates many emerging applications, including immune evasion, enhancements in stability, fluorescent labelling, chemical 5′‐RNA‐capping and the development of functional aptamers. While c...
Saved in:
Published in: | Chembiochem : a European journal of chemical biology 2024-01, Vol.25 (1), p.e202300701-n/a |
---|---|
Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | |
---|---|
cites | cdi_FETCH-LOGICAL-c3681-ff97d4665038d07790cdece966d54977b10bc98b365dde1ec60e77a6dd5a4f983 |
container_end_page | n/a |
container_issue | 1 |
container_start_page | e202300701 |
container_title | Chembiochem : a European journal of chemical biology |
container_volume | 25 |
creator | Schönegger, Eva S. Crisp, Antony Radukic, Marco Burmester, Jonas Frischmuth, Thomas Carell, Thomas |
description | Post‐synthetic modification of nucleic acid structures with clickable functionality is a versatile tool that facilitates many emerging applications, including immune evasion, enhancements in stability, fluorescent labelling, chemical 5′‐RNA‐capping and the development of functional aptamers. While certain chemoenzymatic approaches for 3′‐azido and alkynyl labelling are known, equivalent 5′‐strategies are either inefficient, complex, or require harsh chemical conditions. Here, we present a modular and facile technology to consecutively modify DNA and RNA strands at both ends with click‐modifiable functional groups. Our approach using γ‐modified ATP analogues facilitates T4 PNK‐catalysed 5′‐modification of oligonucleotides, a process that is compatible with TdT‐catalysed 3′‐elongation using 3′‐azido‐2′,3′‐ddGTP. Finally, we demonstrate that our approach is suitable for both oligo‐oligo ligations, as well ssDNA circularization. We anticipate that such approaches will pave the way for the synthesis of highly functionalised oligonucleotides, improving the therapeutic and diagnostic applicability of oligonucleotides such as in the realm of next‐generation sequencing.
A new chemoenzymatic method involving dual incorporation of γ‐ and 3′‐modified NTPs allows sequential 5′‐ and 3′‐end labelling of DNA and RNA molecules. |
doi_str_mv | 10.1002/cbic.202300701 |
format | article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2880104738</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2908968994</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3681-ff97d4665038d07790cdece966d54977b10bc98b365dde1ec60e77a6dd5a4f983</originalsourceid><addsrcrecordid>eNqF0U1P2zAcBnBrAq2s23XHKRIXLi1_x4lfjhA6Vqmi09SdI8d2Wpc0LnYC6o2PsM-4T4KrdiBx2cmW_PPjlwehrxjGGCC9VJVV4xRSAsAAf0BnOCNixCghJ8d5lqZsgD6FsAYAQQn-iAaEcYoJy8-Qnftu5ZaulU0yaXUyk5VpGtsuE1cn88bGlV41xnVWm5B0K-_65Sq56SOftsr5rfOys67d86Kx6v7v859fRqrOPprkbvEzuYrJbtmb8Bmd1rIJ5stxHKLf3yeL4sdoNr-dFlezkSKU41FdC6YzSnMgXANjApQ2yghKdZ4JxioMlRK8IjTX2mCjKBjGJNU6l1ktOBmii0Pu1ruHeG5XbmxQ8VGyNa4PZco5YMgY2dPzd3Tteh8vHJUALigXIotqfFDKuxC8qcuttxvpdyWGcl9CuS-hfC0hbvh2jO2rjdGv_N-vRyAO4Mk2ZvefuLK4nhZv4S9oRpRF</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2908968994</pqid></control><display><type>article</type><title>Orthogonal End Labelling of Oligonucleotides through Dual Incorporation of Click‐Reactive NTP Analogues</title><source>Wiley-Blackwell Read & Publish Collection</source><creator>Schönegger, Eva S. ; Crisp, Antony ; Radukic, Marco ; Burmester, Jonas ; Frischmuth, Thomas ; Carell, Thomas</creator><creatorcontrib>Schönegger, Eva S. ; Crisp, Antony ; Radukic, Marco ; Burmester, Jonas ; Frischmuth, Thomas ; Carell, Thomas</creatorcontrib><description>Post‐synthetic modification of nucleic acid structures with clickable functionality is a versatile tool that facilitates many emerging applications, including immune evasion, enhancements in stability, fluorescent labelling, chemical 5′‐RNA‐capping and the development of functional aptamers. While certain chemoenzymatic approaches for 3′‐azido and alkynyl labelling are known, equivalent 5′‐strategies are either inefficient, complex, or require harsh chemical conditions. Here, we present a modular and facile technology to consecutively modify DNA and RNA strands at both ends with click‐modifiable functional groups. Our approach using γ‐modified ATP analogues facilitates T4 PNK‐catalysed 5′‐modification of oligonucleotides, a process that is compatible with TdT‐catalysed 3′‐elongation using 3′‐azido‐2′,3′‐ddGTP. Finally, we demonstrate that our approach is suitable for both oligo‐oligo ligations, as well ssDNA circularization. We anticipate that such approaches will pave the way for the synthesis of highly functionalised oligonucleotides, improving the therapeutic and diagnostic applicability of oligonucleotides such as in the realm of next‐generation sequencing.
A new chemoenzymatic method involving dual incorporation of γ‐ and 3′‐modified NTPs allows sequential 5′‐ and 3′‐end labelling of DNA and RNA molecules.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.202300701</identifier><identifier>PMID: 37861375</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aptamers ; chemoenzymatic ; Click Chemistry ; click-functionalised nucleotides ; DNA - chemistry ; DNA nucleotidylexotransferase ; Elongation ; Fluorescence ; Functional groups ; Labeling ; labelling ; Nucleic acids ; Oligonucleotides ; Oligonucleotides - chemistry ; Ribonucleic acid ; RNA ; RNA - chemistry</subject><ispartof>Chembiochem : a European journal of chemical biology, 2024-01, Vol.25 (1), p.e202300701-n/a</ispartof><rights>2023 The Authors. ChemBioChem published by Wiley-VCH GmbH</rights><rights>2023 The Authors. ChemBioChem published by Wiley-VCH GmbH.</rights><rights>2023. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3681-ff97d4665038d07790cdece966d54977b10bc98b365dde1ec60e77a6dd5a4f983</cites><orcidid>0000-0001-8355-6458 ; 0000-0003-1860-1739 ; 0000-0001-7173-4376 ; 0000-0001-7898-2831</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37861375$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schönegger, Eva S.</creatorcontrib><creatorcontrib>Crisp, Antony</creatorcontrib><creatorcontrib>Radukic, Marco</creatorcontrib><creatorcontrib>Burmester, Jonas</creatorcontrib><creatorcontrib>Frischmuth, Thomas</creatorcontrib><creatorcontrib>Carell, Thomas</creatorcontrib><title>Orthogonal End Labelling of Oligonucleotides through Dual Incorporation of Click‐Reactive NTP Analogues</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>Chembiochem</addtitle><description>Post‐synthetic modification of nucleic acid structures with clickable functionality is a versatile tool that facilitates many emerging applications, including immune evasion, enhancements in stability, fluorescent labelling, chemical 5′‐RNA‐capping and the development of functional aptamers. While certain chemoenzymatic approaches for 3′‐azido and alkynyl labelling are known, equivalent 5′‐strategies are either inefficient, complex, or require harsh chemical conditions. Here, we present a modular and facile technology to consecutively modify DNA and RNA strands at both ends with click‐modifiable functional groups. Our approach using γ‐modified ATP analogues facilitates T4 PNK‐catalysed 5′‐modification of oligonucleotides, a process that is compatible with TdT‐catalysed 3′‐elongation using 3′‐azido‐2′,3′‐ddGTP. Finally, we demonstrate that our approach is suitable for both oligo‐oligo ligations, as well ssDNA circularization. We anticipate that such approaches will pave the way for the synthesis of highly functionalised oligonucleotides, improving the therapeutic and diagnostic applicability of oligonucleotides such as in the realm of next‐generation sequencing.
A new chemoenzymatic method involving dual incorporation of γ‐ and 3′‐modified NTPs allows sequential 5′‐ and 3′‐end labelling of DNA and RNA molecules.</description><subject>Aptamers</subject><subject>chemoenzymatic</subject><subject>Click Chemistry</subject><subject>click-functionalised nucleotides</subject><subject>DNA - chemistry</subject><subject>DNA nucleotidylexotransferase</subject><subject>Elongation</subject><subject>Fluorescence</subject><subject>Functional groups</subject><subject>Labeling</subject><subject>labelling</subject><subject>Nucleic acids</subject><subject>Oligonucleotides</subject><subject>Oligonucleotides - chemistry</subject><subject>Ribonucleic acid</subject><subject>RNA</subject><subject>RNA - chemistry</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqF0U1P2zAcBnBrAq2s23XHKRIXLi1_x4lfjhA6Vqmi09SdI8d2Wpc0LnYC6o2PsM-4T4KrdiBx2cmW_PPjlwehrxjGGCC9VJVV4xRSAsAAf0BnOCNixCghJ8d5lqZsgD6FsAYAQQn-iAaEcYoJy8-Qnftu5ZaulU0yaXUyk5VpGtsuE1cn88bGlV41xnVWm5B0K-_65Sq56SOftsr5rfOys67d86Kx6v7v859fRqrOPprkbvEzuYrJbtmb8Bmd1rIJ5stxHKLf3yeL4sdoNr-dFlezkSKU41FdC6YzSnMgXANjApQ2yghKdZ4JxioMlRK8IjTX2mCjKBjGJNU6l1ktOBmii0Pu1ruHeG5XbmxQ8VGyNa4PZco5YMgY2dPzd3Tteh8vHJUALigXIotqfFDKuxC8qcuttxvpdyWGcl9CuS-hfC0hbvh2jO2rjdGv_N-vRyAO4Mk2ZvefuLK4nhZv4S9oRpRF</recordid><startdate>20240102</startdate><enddate>20240102</enddate><creator>Schönegger, Eva S.</creator><creator>Crisp, Antony</creator><creator>Radukic, Marco</creator><creator>Burmester, Jonas</creator><creator>Frischmuth, Thomas</creator><creator>Carell, Thomas</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><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>7QL</scope><scope>7QO</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8355-6458</orcidid><orcidid>https://orcid.org/0000-0003-1860-1739</orcidid><orcidid>https://orcid.org/0000-0001-7173-4376</orcidid><orcidid>https://orcid.org/0000-0001-7898-2831</orcidid></search><sort><creationdate>20240102</creationdate><title>Orthogonal End Labelling of Oligonucleotides through Dual Incorporation of Click‐Reactive NTP Analogues</title><author>Schönegger, Eva S. ; Crisp, Antony ; Radukic, Marco ; Burmester, Jonas ; Frischmuth, Thomas ; Carell, Thomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3681-ff97d4665038d07790cdece966d54977b10bc98b365dde1ec60e77a6dd5a4f983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aptamers</topic><topic>chemoenzymatic</topic><topic>Click Chemistry</topic><topic>click-functionalised nucleotides</topic><topic>DNA - chemistry</topic><topic>DNA nucleotidylexotransferase</topic><topic>Elongation</topic><topic>Fluorescence</topic><topic>Functional groups</topic><topic>Labeling</topic><topic>labelling</topic><topic>Nucleic acids</topic><topic>Oligonucleotides</topic><topic>Oligonucleotides - chemistry</topic><topic>Ribonucleic acid</topic><topic>RNA</topic><topic>RNA - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schönegger, Eva S.</creatorcontrib><creatorcontrib>Crisp, Antony</creatorcontrib><creatorcontrib>Radukic, Marco</creatorcontrib><creatorcontrib>Burmester, Jonas</creatorcontrib><creatorcontrib>Frischmuth, Thomas</creatorcontrib><creatorcontrib>Carell, Thomas</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>Wiley Online Library Free Content</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schönegger, Eva S.</au><au>Crisp, Antony</au><au>Radukic, Marco</au><au>Burmester, Jonas</au><au>Frischmuth, Thomas</au><au>Carell, Thomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Orthogonal End Labelling of Oligonucleotides through Dual Incorporation of Click‐Reactive NTP Analogues</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>Chembiochem</addtitle><date>2024-01-02</date><risdate>2024</risdate><volume>25</volume><issue>1</issue><spage>e202300701</spage><epage>n/a</epage><pages>e202300701-n/a</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>Post‐synthetic modification of nucleic acid structures with clickable functionality is a versatile tool that facilitates many emerging applications, including immune evasion, enhancements in stability, fluorescent labelling, chemical 5′‐RNA‐capping and the development of functional aptamers. While certain chemoenzymatic approaches for 3′‐azido and alkynyl labelling are known, equivalent 5′‐strategies are either inefficient, complex, or require harsh chemical conditions. Here, we present a modular and facile technology to consecutively modify DNA and RNA strands at both ends with click‐modifiable functional groups. Our approach using γ‐modified ATP analogues facilitates T4 PNK‐catalysed 5′‐modification of oligonucleotides, a process that is compatible with TdT‐catalysed 3′‐elongation using 3′‐azido‐2′,3′‐ddGTP. Finally, we demonstrate that our approach is suitable for both oligo‐oligo ligations, as well ssDNA circularization. We anticipate that such approaches will pave the way for the synthesis of highly functionalised oligonucleotides, improving the therapeutic and diagnostic applicability of oligonucleotides such as in the realm of next‐generation sequencing.
A new chemoenzymatic method involving dual incorporation of γ‐ and 3′‐modified NTPs allows sequential 5′‐ and 3′‐end labelling of DNA and RNA molecules.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>37861375</pmid><doi>10.1002/cbic.202300701</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8355-6458</orcidid><orcidid>https://orcid.org/0000-0003-1860-1739</orcidid><orcidid>https://orcid.org/0000-0001-7173-4376</orcidid><orcidid>https://orcid.org/0000-0001-7898-2831</orcidid><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1439-4227 |
ispartof | Chembiochem : a European journal of chemical biology, 2024-01, Vol.25 (1), p.e202300701-n/a |
issn | 1439-4227 1439-7633 |
language | eng |
recordid | cdi_proquest_miscellaneous_2880104738 |
source | Wiley-Blackwell Read & Publish Collection |
subjects | Aptamers chemoenzymatic Click Chemistry click-functionalised nucleotides DNA - chemistry DNA nucleotidylexotransferase Elongation Fluorescence Functional groups Labeling labelling Nucleic acids Oligonucleotides Oligonucleotides - chemistry Ribonucleic acid RNA RNA - chemistry |
title | Orthogonal End Labelling of Oligonucleotides through Dual Incorporation of Click‐Reactive NTP Analogues |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T12%3A20%3A12IST&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=Orthogonal%20End%20Labelling%20of%20Oligonucleotides%20through%20Dual%20Incorporation%20of%20Click%E2%80%90Reactive%20NTP%20Analogues&rft.jtitle=Chembiochem%20:%20a%20European%20journal%20of%20chemical%20biology&rft.au=Sch%C3%B6negger,%20Eva%20S.&rft.date=2024-01-02&rft.volume=25&rft.issue=1&rft.spage=e202300701&rft.epage=n/a&rft.pages=e202300701-n/a&rft.issn=1439-4227&rft.eissn=1439-7633&rft_id=info:doi/10.1002/cbic.202300701&rft_dat=%3Cproquest_cross%3E2908968994%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3681-ff97d4665038d07790cdece966d54977b10bc98b365dde1ec60e77a6dd5a4f983%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2908968994&rft_id=info:pmid/37861375&rfr_iscdi=true |