Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA

Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA

5-Hydroxymethylcytosine and uracil are epigenetic nucleobases, but their biological roles are still unclear. We present the synthesis of 2-nitrobenzyl photocaged 5-hydroxymethyl-2′-deoxycytidine and uridine 3′-O-phosphoramidites and their use in automated solid-phase synthesis of oligonucleotides (O...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2020-11, Vol.22 (22), p.9081-9085
Hauptverfasser: Chakrapani, Aswathi, Vaňková Hausnerová, Viola, Ruiz-Larrabeiti, Olatz, Pohl, Radek, Krásný, Libor, Hocek, Michal
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 9085
container_issue 22
container_start_page 9081
container_title Organic letters
container_volume 22
creator Chakrapani, Aswathi
Vaňková Hausnerová, Viola
Ruiz-Larrabeiti, Olatz
Pohl, Radek
Krásný, Libor
Hocek, Michal
description 5-Hydroxymethylcytosine and uracil are epigenetic nucleobases, but their biological roles are still unclear. We present the synthesis of 2-nitrobenzyl photocaged 5-hydroxymethyl-2′-deoxycytidine and uridine 3′-O-phosphoramidites and their use in automated solid-phase synthesis of oligonucleotides (ONs) modified at specific positions. The ONs were used as primers for PCR to construct DNA templates modified in the promoter region that allowed switching of transcription through photochemical uncaging.
doi_str_mv 10.1021/acs.orglett.0c03462
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2458728716</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2458728716</sourcerecordid><originalsourceid>FETCH-LOGICAL-a367t-994c6fd52bc9309b8d7ea8eea39b15868112e69ec5e51b96b0143b0cf16b93ad3</originalsourceid><addsrcrecordid>eNp9kEtOwzAQhiMEEqVwAjZelkVaO06ceFmVR5GqggSsI9uZpK7SONguIgskrsAVOQkprViymtH8D2m-ILgkeExwRCZCubGxVQ3ej7HCNGbRUTAgSUTDFCfR8d_O8Glw5twaY9Jf-CD4eFwZb5SooEDJ9-fXaN4V1rx3G_Crrr5qO6s3utANoOVW1WCcLgD1GdeujBU7yYNDpbHoqQWlS63Qb6NQXr8JL2QN6KbVFTTge20hJNS6qZAp0fVyeh6clKJ2cHGYw-Dl9uZ5Ng8XD3f3s-kiFJSlPuQ8VqwskkgqTjGXWZGCyAAE5ZIkGcsIiYBxUAkkRHImMYmpxKokTHIqCjoMRvve1prXLTifb7RTUNeiAbN1eRQnWRplKWG9le6tyhrnLJR52yMQtssJznew8x52foCdH2D3qck-tRPXZmub_p1_Ez8dg4m1</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2458728716</pqid></control><display><type>article</type><title>Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA</title><source>ACS Publications</source><creator>Chakrapani, Aswathi ; Vaňková Hausnerová, Viola ; Ruiz-Larrabeiti, Olatz ; Pohl, Radek ; Krásný, Libor ; Hocek, Michal</creator><creatorcontrib>Chakrapani, Aswathi ; Vaňková Hausnerová, Viola ; Ruiz-Larrabeiti, Olatz ; Pohl, Radek ; Krásný, Libor ; Hocek, Michal</creatorcontrib><description>5-Hydroxymethylcytosine and uracil are epigenetic nucleobases, but their biological roles are still unclear. We present the synthesis of 2-nitrobenzyl photocaged 5-hydroxymethyl-2′-deoxycytidine and uridine 3′-O-phosphoramidites and their use in automated solid-phase synthesis of oligonucleotides (ONs) modified at specific positions. The ONs were used as primers for PCR to construct DNA templates modified in the promoter region that allowed switching of transcription through photochemical uncaging.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c03462</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic letters, 2020-11, Vol.22 (22), p.9081-9085</ispartof><rights>2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a367t-994c6fd52bc9309b8d7ea8eea39b15868112e69ec5e51b96b0143b0cf16b93ad3</citedby><cites>FETCH-LOGICAL-a367t-994c6fd52bc9309b8d7ea8eea39b15868112e69ec5e51b96b0143b0cf16b93ad3</cites><orcidid>0000-0002-1113-2047</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.0c03462$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.0c03462$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Chakrapani, Aswathi</creatorcontrib><creatorcontrib>Vaňková Hausnerová, Viola</creatorcontrib><creatorcontrib>Ruiz-Larrabeiti, Olatz</creatorcontrib><creatorcontrib>Pohl, Radek</creatorcontrib><creatorcontrib>Krásný, Libor</creatorcontrib><creatorcontrib>Hocek, Michal</creatorcontrib><title>Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>5-Hydroxymethylcytosine and uracil are epigenetic nucleobases, but their biological roles are still unclear. We present the synthesis of 2-nitrobenzyl photocaged 5-hydroxymethyl-2′-deoxycytidine and uridine 3′-O-phosphoramidites and their use in automated solid-phase synthesis of oligonucleotides (ONs) modified at specific positions. The ONs were used as primers for PCR to construct DNA templates modified in the promoter region that allowed switching of transcription through photochemical uncaging.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEtOwzAQhiMEEqVwAjZelkVaO06ceFmVR5GqggSsI9uZpK7SONguIgskrsAVOQkprViymtH8D2m-ILgkeExwRCZCubGxVQ3ej7HCNGbRUTAgSUTDFCfR8d_O8Glw5twaY9Jf-CD4eFwZb5SooEDJ9-fXaN4V1rx3G_Crrr5qO6s3utANoOVW1WCcLgD1GdeujBU7yYNDpbHoqQWlS63Qb6NQXr8JL2QN6KbVFTTge20hJNS6qZAp0fVyeh6clKJ2cHGYw-Dl9uZ5Ng8XD3f3s-kiFJSlPuQ8VqwskkgqTjGXWZGCyAAE5ZIkGcsIiYBxUAkkRHImMYmpxKokTHIqCjoMRvve1prXLTifb7RTUNeiAbN1eRQnWRplKWG9le6tyhrnLJR52yMQtssJznew8x52foCdH2D3qck-tRPXZmub_p1_Ez8dg4m1</recordid><startdate>20201120</startdate><enddate>20201120</enddate><creator>Chakrapani, Aswathi</creator><creator>Vaňková Hausnerová, Viola</creator><creator>Ruiz-Larrabeiti, Olatz</creator><creator>Pohl, Radek</creator><creator>Krásný, Libor</creator><creator>Hocek, Michal</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1113-2047</orcidid></search><sort><creationdate>20201120</creationdate><title>Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA</title><author>Chakrapani, Aswathi ; Vaňková Hausnerová, Viola ; Ruiz-Larrabeiti, Olatz ; Pohl, Radek ; Krásný, Libor ; Hocek, Michal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a367t-994c6fd52bc9309b8d7ea8eea39b15868112e69ec5e51b96b0143b0cf16b93ad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chakrapani, Aswathi</creatorcontrib><creatorcontrib>Vaňková Hausnerová, Viola</creatorcontrib><creatorcontrib>Ruiz-Larrabeiti, Olatz</creatorcontrib><creatorcontrib>Pohl, Radek</creatorcontrib><creatorcontrib>Krásný, Libor</creatorcontrib><creatorcontrib>Hocek, Michal</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chakrapani, Aswathi</au><au>Vaňková Hausnerová, Viola</au><au>Ruiz-Larrabeiti, Olatz</au><au>Pohl, Radek</au><au>Krásný, Libor</au><au>Hocek, Michal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2020-11-20</date><risdate>2020</risdate><volume>22</volume><issue>22</issue><spage>9081</spage><epage>9085</epage><pages>9081-9085</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>5-Hydroxymethylcytosine and uracil are epigenetic nucleobases, but their biological roles are still unclear. We present the synthesis of 2-nitrobenzyl photocaged 5-hydroxymethyl-2′-deoxycytidine and uridine 3′-O-phosphoramidites and their use in automated solid-phase synthesis of oligonucleotides (ONs) modified at specific positions. The ONs were used as primers for PCR to construct DNA templates modified in the promoter region that allowed switching of transcription through photochemical uncaging.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.orglett.0c03462</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1113-2047</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-11, Vol.22 (22), p.9081-9085
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2458728716
source ACS Publications
title Photocaged 5‑(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T11%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_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Photocaged%205%E2%80%91(Hydroxymethyl)pyrimidine%20Nucleoside%20Phosphoramidites%20for%20Specific%20Photoactivatable%20Epigenetic%20Labeling%20of%20DNA&rft.jtitle=Organic%20letters&rft.au=Chakrapani,%20Aswathi&rft.date=2020-11-20&rft.volume=22&rft.issue=22&rft.spage=9081&rft.epage=9085&rft.pages=9081-9085&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c03462&rft_dat=%3Cproquest_cross%3E2458728716%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=2458728716&rft_id=info:pmid/&rfr_iscdi=true