Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange
A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerabili...
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| Veröffentlicht in: | Angewandte Chemie 2019-04, Vol.131 (15), p.4945-4949 |
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| creator | Palazzolo, Alberto Feuillastre, Sophie Pfeifer, Viktor Garcia‐Argote, Sébastien Bouzouita, Donia Tricard, Simon Chollet, Céline Marcon, Elodie Buisson, David‐Alexandre Cholet, Sophie Fenaille, François Lippens, Guy Chaudret, Bruno Pieters, Grégory |
| description | A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.
Ein guter Tausch: Ein allgemeiner Ansatz für Wasserstoffisotopenaustausch in Nukleobasederivaten in späten Synthesephasen wird vorgestellt. Die Reaktion, die durch Ruthenium‐Nanopartikel mit D2 oder T2 als Isotopenquelle katalysiert wird, weist einen breiten Substratbereich auf und erleichtert den Zugang zu diagnostischen Werkzeugen in der Wirkstoffentwicklung. |
| doi_str_mv | 10.1002/ange.201813946 |
| format | Article |
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Ein guter Tausch: Ein allgemeiner Ansatz für Wasserstoffisotopenaustausch in Nukleobasederivaten in späten Synthesephasen wird vorgestellt. Die Reaktion, die durch Ruthenium‐Nanopartikel mit D2 oder T2 als Isotopenquelle katalysiert wird, weist einen breiten Substratbereich auf und erleichtert den Zugang zu diagnostischen Werkzeugen in der Wirkstoffentwicklung.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201813946</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>C-H-Aktivierung ; Chemistry ; Deuteration ; Diagnostic software ; Diagnostic systems ; Drug discovery ; Drugs ; Exchanging ; Isotope ; Isotopenmarkierung ; Nanoparticles ; Nanopartikel ; Nukleotide ; Oligonucleotides ; Pharmaceuticals ; Ruthenium ; Substrates</subject><ispartof>Angewandte Chemie, 2019-04, Vol.131 (15), p.4945-4949</ispartof><rights>2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2686-4e50cf284784d623d5a38e592f7ff302249189f9f477c1f700aca17fe504d48a3</citedby><cites>FETCH-LOGICAL-c2686-4e50cf284784d623d5a38e592f7ff302249189f9f477c1f700aca17fe504d48a3</cites><orcidid>0000-0002-3924-8287</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201813946$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201813946$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Palazzolo, Alberto</creatorcontrib><creatorcontrib>Feuillastre, Sophie</creatorcontrib><creatorcontrib>Pfeifer, Viktor</creatorcontrib><creatorcontrib>Garcia‐Argote, Sébastien</creatorcontrib><creatorcontrib>Bouzouita, Donia</creatorcontrib><creatorcontrib>Tricard, Simon</creatorcontrib><creatorcontrib>Chollet, Céline</creatorcontrib><creatorcontrib>Marcon, Elodie</creatorcontrib><creatorcontrib>Buisson, David‐Alexandre</creatorcontrib><creatorcontrib>Cholet, Sophie</creatorcontrib><creatorcontrib>Fenaille, François</creatorcontrib><creatorcontrib>Lippens, Guy</creatorcontrib><creatorcontrib>Chaudret, Bruno</creatorcontrib><creatorcontrib>Pieters, Grégory</creatorcontrib><title>Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange</title><title>Angewandte Chemie</title><description>A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.
Ein guter Tausch: Ein allgemeiner Ansatz für Wasserstoffisotopenaustausch in Nukleobasederivaten in späten Synthesephasen wird vorgestellt. Die Reaktion, die durch Ruthenium‐Nanopartikel mit D2 oder T2 als Isotopenquelle katalysiert wird, weist einen breiten Substratbereich auf und erleichtert den Zugang zu diagnostischen Werkzeugen in der Wirkstoffentwicklung.</description><subject>C-H-Aktivierung</subject><subject>Chemistry</subject><subject>Deuteration</subject><subject>Diagnostic software</subject><subject>Diagnostic systems</subject><subject>Drug discovery</subject><subject>Drugs</subject><subject>Exchanging</subject><subject>Isotope</subject><subject>Isotopenmarkierung</subject><subject>Nanoparticles</subject><subject>Nanopartikel</subject><subject>Nukleotide</subject><subject>Oligonucleotides</subject><subject>Pharmaceuticals</subject><subject>Ruthenium</subject><subject>Substrates</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkL1OwzAURi0EEqWwMltiTrEdJ3bGqpS2UlUYyhwZ5zp1lcbFTgRdEI_AM_IkpC2CkenqSufcnw-ha0oGlBB2q-oSBoxQSeOMpyeoRxNGo1gk4hT1COE8koxn5-gihDUhJGUi66H3sTFWW6gbPNQaQsCNw3fQNuBVAwVWdYGX3jb20C1aXYF7VgHw40r5jdIdabWqwgF8qGzp6gPT2AICboOtSzzdFd6VUH99fM6Ca9wW8PhNr_b3XqIz09lw9VP76Ol-vBxNo_nDZDYaziPNUplGHBKiDZNcSF6kLC4SFUtIMmaEMTFh3V9UZiYzXAhNjSBEaUWF6TRecKniPro5zt1699JCaPK1a33drcwZzdIkEVKQjhocKe1dCB5MvvV2o_wupyTfZ5zvb85_M-6E7Ci82gp2_9D5cDEZ_7nfolGDHQ</recordid><startdate>20190401</startdate><enddate>20190401</enddate><creator>Palazzolo, Alberto</creator><creator>Feuillastre, Sophie</creator><creator>Pfeifer, Viktor</creator><creator>Garcia‐Argote, Sébastien</creator><creator>Bouzouita, Donia</creator><creator>Tricard, Simon</creator><creator>Chollet, Céline</creator><creator>Marcon, Elodie</creator><creator>Buisson, David‐Alexandre</creator><creator>Cholet, Sophie</creator><creator>Fenaille, François</creator><creator>Lippens, Guy</creator><creator>Chaudret, Bruno</creator><creator>Pieters, Grégory</creator><general>Wiley Subscription Services, Inc</general><scope>24P</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><orcidid>https://orcid.org/0000-0002-3924-8287</orcidid></search><sort><creationdate>20190401</creationdate><title>Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange</title><author>Palazzolo, Alberto ; Feuillastre, Sophie ; Pfeifer, Viktor ; Garcia‐Argote, Sébastien ; Bouzouita, Donia ; Tricard, Simon ; Chollet, Céline ; Marcon, Elodie ; Buisson, David‐Alexandre ; Cholet, Sophie ; Fenaille, François ; Lippens, Guy ; Chaudret, Bruno ; Pieters, Grégory</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2686-4e50cf284784d623d5a38e592f7ff302249189f9f477c1f700aca17fe504d48a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>C-H-Aktivierung</topic><topic>Chemistry</topic><topic>Deuteration</topic><topic>Diagnostic software</topic><topic>Diagnostic systems</topic><topic>Drug discovery</topic><topic>Drugs</topic><topic>Exchanging</topic><topic>Isotope</topic><topic>Isotopenmarkierung</topic><topic>Nanoparticles</topic><topic>Nanopartikel</topic><topic>Nukleotide</topic><topic>Oligonucleotides</topic><topic>Pharmaceuticals</topic><topic>Ruthenium</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Palazzolo, Alberto</creatorcontrib><creatorcontrib>Feuillastre, Sophie</creatorcontrib><creatorcontrib>Pfeifer, Viktor</creatorcontrib><creatorcontrib>Garcia‐Argote, Sébastien</creatorcontrib><creatorcontrib>Bouzouita, Donia</creatorcontrib><creatorcontrib>Tricard, Simon</creatorcontrib><creatorcontrib>Chollet, Céline</creatorcontrib><creatorcontrib>Marcon, Elodie</creatorcontrib><creatorcontrib>Buisson, David‐Alexandre</creatorcontrib><creatorcontrib>Cholet, Sophie</creatorcontrib><creatorcontrib>Fenaille, François</creatorcontrib><creatorcontrib>Lippens, Guy</creatorcontrib><creatorcontrib>Chaudret, Bruno</creatorcontrib><creatorcontrib>Pieters, Grégory</creatorcontrib><collection>Wiley Online Library Open Access</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><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Palazzolo, Alberto</au><au>Feuillastre, Sophie</au><au>Pfeifer, Viktor</au><au>Garcia‐Argote, Sébastien</au><au>Bouzouita, Donia</au><au>Tricard, Simon</au><au>Chollet, Céline</au><au>Marcon, Elodie</au><au>Buisson, David‐Alexandre</au><au>Cholet, Sophie</au><au>Fenaille, François</au><au>Lippens, Guy</au><au>Chaudret, Bruno</au><au>Pieters, Grégory</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange</atitle><jtitle>Angewandte Chemie</jtitle><date>2019-04-01</date><risdate>2019</risdate><volume>131</volume><issue>15</issue><spage>4945</spage><epage>4949</epage><pages>4945-4949</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.
Ein guter Tausch: Ein allgemeiner Ansatz für Wasserstoffisotopenaustausch in Nukleobasederivaten in späten Synthesephasen wird vorgestellt. Die Reaktion, die durch Ruthenium‐Nanopartikel mit D2 oder T2 als Isotopenquelle katalysiert wird, weist einen breiten Substratbereich auf und erleichtert den Zugang zu diagnostischen Werkzeugen in der Wirkstoffentwicklung.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201813946</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-3924-8287</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | C-H-Aktivierung Chemistry Deuteration Diagnostic software Diagnostic systems Drug discovery Drugs Exchanging Isotope Isotopenmarkierung Nanoparticles Nanopartikel Nukleotide Oligonucleotides Pharmaceuticals Ruthenium Substrates |
| title | Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange |
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