Intramolecular Hydrogen Bonding in N 6 -Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy
Two forms were found in the NMR spectra of N -substituted 2-chloroadenosines. The proportion of the mini-form was 11-32% of the main form. It was characterized by a separate set of signals in COSY, N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramol...
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| Veröffentlicht in: | International journal of molecular sciences 2023-06, Vol.24 (11) |
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| creator | Berzina, Maria Ya Eletskaya, Barbara Z Kayushin, Alexei L Dorofeeva, Elena V Lutonina, Olga I Fateev, Ilya V Zhavoronkova, Olga N Bashorin, Arthur R Arnautova, Alexandra O Smirnova, Olga S Antonov, Konstantin V Paramonov, Alexander S Dubinnyi, Maxim A Esipov, Roman S Miroshnikov, Anatoly I Konstantinova, Irina D |
| description | Two forms were found in the NMR spectra of N
-substituted 2-chloroadenosines. The proportion of the mini-form was 11-32% of the main form. It was characterized by a separate set of signals in COSY,
N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramolecular hydrogen bond between the N7 atom of purine and the N
-CH proton of the substituent. The
H,
N-HMBC spectrum confirmed the presence of a hydrogen bond in the mini-form of the nucleoside and its absence in the main form. Compounds incapable of forming such a hydrogen bond were synthesized. In these compounds, either the N7 atom of the purine or the N
-CH proton of the substituent was absent. The mini-form was not found in the NMR spectra of these nucleosides, confirming the importance of the intramolecular hydrogen bond in its formation. |
| format | Article |
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-substituted 2-chloroadenosines. The proportion of the mini-form was 11-32% of the main form. It was characterized by a separate set of signals in COSY,
N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramolecular hydrogen bond between the N7 atom of purine and the N
-CH proton of the substituent. The
H,
N-HMBC spectrum confirmed the presence of a hydrogen bond in the mini-form of the nucleoside and its absence in the main form. Compounds incapable of forming such a hydrogen bond were synthesized. In these compounds, either the N7 atom of the purine or the N
-CH proton of the substituent was absent. The mini-form was not found in the NMR spectra of these nucleosides, confirming the importance of the intramolecular hydrogen bond in its formation.</description><identifier>EISSN: 1422-0067</identifier><identifier>PMID: 37298648</identifier><language>eng</language><publisher>Switzerland</publisher><ispartof>International journal of molecular sciences, 2023-06, Vol.24 (11)</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-9552-7141 ; 0000-0002-5684-8188 ; 0000-0002-5463-0169 ; 0000-0003-3614-560X ; 0000-0003-3413-0180 ; 0000-0002-8571-4197 ; 0000-0002-3231-5838</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37298648$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Berzina, Maria Ya</creatorcontrib><creatorcontrib>Eletskaya, Barbara Z</creatorcontrib><creatorcontrib>Kayushin, Alexei L</creatorcontrib><creatorcontrib>Dorofeeva, Elena V</creatorcontrib><creatorcontrib>Lutonina, Olga I</creatorcontrib><creatorcontrib>Fateev, Ilya V</creatorcontrib><creatorcontrib>Zhavoronkova, Olga N</creatorcontrib><creatorcontrib>Bashorin, Arthur R</creatorcontrib><creatorcontrib>Arnautova, Alexandra O</creatorcontrib><creatorcontrib>Smirnova, Olga S</creatorcontrib><creatorcontrib>Antonov, Konstantin V</creatorcontrib><creatorcontrib>Paramonov, Alexander S</creatorcontrib><creatorcontrib>Dubinnyi, Maxim A</creatorcontrib><creatorcontrib>Esipov, Roman S</creatorcontrib><creatorcontrib>Miroshnikov, Anatoly I</creatorcontrib><creatorcontrib>Konstantinova, Irina D</creatorcontrib><title>Intramolecular Hydrogen Bonding in N 6 -Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>Two forms were found in the NMR spectra of N
-substituted 2-chloroadenosines. The proportion of the mini-form was 11-32% of the main form. It was characterized by a separate set of signals in COSY,
N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramolecular hydrogen bond between the N7 atom of purine and the N
-CH proton of the substituent. The
H,
N-HMBC spectrum confirmed the presence of a hydrogen bond in the mini-form of the nucleoside and its absence in the main form. Compounds incapable of forming such a hydrogen bond were synthesized. In these compounds, either the N7 atom of the purine or the N
-CH proton of the substituent was absent. The mini-form was not found in the NMR spectra of these nucleosides, confirming the importance of the intramolecular hydrogen bond in its formation.</description><issn>1422-0067</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFjrsOgjAUQBsT4_sXzP0BEiyIj1GC0UEGcSeFXrQGeklbTPh7HXR2OjnJGc6ATVYh557vR5sxm1r79H0e8PVuxMbBhu-2UbidsOqsnREN1Vh2tTBw6qWhO2o4kJZK30FpSCECL-sK65TrHErgXvyoyZCQqMkqjXYPyUt9rESoDDWQXq6QtVg6Q7aktp-zYSVqi4svZ2x5TG7xyWu7okGZt0Y1wvT5byz4G7wBj4JEBA</recordid><startdate>20230602</startdate><enddate>20230602</enddate><creator>Berzina, Maria Ya</creator><creator>Eletskaya, Barbara Z</creator><creator>Kayushin, Alexei L</creator><creator>Dorofeeva, Elena V</creator><creator>Lutonina, Olga I</creator><creator>Fateev, Ilya V</creator><creator>Zhavoronkova, Olga N</creator><creator>Bashorin, Arthur R</creator><creator>Arnautova, Alexandra O</creator><creator>Smirnova, Olga S</creator><creator>Antonov, Konstantin V</creator><creator>Paramonov, Alexander S</creator><creator>Dubinnyi, Maxim A</creator><creator>Esipov, Roman S</creator><creator>Miroshnikov, Anatoly I</creator><creator>Konstantinova, Irina D</creator><scope>NPM</scope><orcidid>https://orcid.org/0000-0002-9552-7141</orcidid><orcidid>https://orcid.org/0000-0002-5684-8188</orcidid><orcidid>https://orcid.org/0000-0002-5463-0169</orcidid><orcidid>https://orcid.org/0000-0003-3614-560X</orcidid><orcidid>https://orcid.org/0000-0003-3413-0180</orcidid><orcidid>https://orcid.org/0000-0002-8571-4197</orcidid><orcidid>https://orcid.org/0000-0002-3231-5838</orcidid></search><sort><creationdate>20230602</creationdate><title>Intramolecular Hydrogen Bonding in N 6 -Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy</title><author>Berzina, Maria Ya ; Eletskaya, Barbara Z ; Kayushin, Alexei L ; Dorofeeva, Elena V ; Lutonina, Olga I ; Fateev, Ilya V ; Zhavoronkova, Olga N ; Bashorin, Arthur R ; Arnautova, Alexandra O ; Smirnova, Olga S ; Antonov, Konstantin V ; Paramonov, Alexander S ; Dubinnyi, Maxim A ; Esipov, Roman S ; Miroshnikov, Anatoly I ; Konstantinova, Irina D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-pubmed_primary_372986483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Berzina, Maria Ya</creatorcontrib><creatorcontrib>Eletskaya, Barbara Z</creatorcontrib><creatorcontrib>Kayushin, Alexei L</creatorcontrib><creatorcontrib>Dorofeeva, Elena V</creatorcontrib><creatorcontrib>Lutonina, Olga I</creatorcontrib><creatorcontrib>Fateev, Ilya V</creatorcontrib><creatorcontrib>Zhavoronkova, Olga N</creatorcontrib><creatorcontrib>Bashorin, Arthur R</creatorcontrib><creatorcontrib>Arnautova, Alexandra O</creatorcontrib><creatorcontrib>Smirnova, Olga S</creatorcontrib><creatorcontrib>Antonov, Konstantin V</creatorcontrib><creatorcontrib>Paramonov, Alexander S</creatorcontrib><creatorcontrib>Dubinnyi, Maxim A</creatorcontrib><creatorcontrib>Esipov, Roman S</creatorcontrib><creatorcontrib>Miroshnikov, Anatoly I</creatorcontrib><creatorcontrib>Konstantinova, Irina D</creatorcontrib><collection>PubMed</collection><jtitle>International journal of molecular sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Berzina, Maria Ya</au><au>Eletskaya, Barbara Z</au><au>Kayushin, Alexei L</au><au>Dorofeeva, Elena V</au><au>Lutonina, Olga I</au><au>Fateev, Ilya V</au><au>Zhavoronkova, Olga N</au><au>Bashorin, Arthur R</au><au>Arnautova, Alexandra O</au><au>Smirnova, Olga S</au><au>Antonov, Konstantin V</au><au>Paramonov, Alexander S</au><au>Dubinnyi, Maxim A</au><au>Esipov, Roman S</au><au>Miroshnikov, Anatoly I</au><au>Konstantinova, Irina D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intramolecular Hydrogen Bonding in N 6 -Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2023-06-02</date><risdate>2023</risdate><volume>24</volume><issue>11</issue><eissn>1422-0067</eissn><abstract>Two forms were found in the NMR spectra of N
-substituted 2-chloroadenosines. The proportion of the mini-form was 11-32% of the main form. It was characterized by a separate set of signals in COSY,
N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramolecular hydrogen bond between the N7 atom of purine and the N
-CH proton of the substituent. The
H,
N-HMBC spectrum confirmed the presence of a hydrogen bond in the mini-form of the nucleoside and its absence in the main form. Compounds incapable of forming such a hydrogen bond were synthesized. In these compounds, either the N7 atom of the purine or the N
-CH proton of the substituent was absent. The mini-form was not found in the NMR spectra of these nucleosides, confirming the importance of the intramolecular hydrogen bond in its formation.</abstract><cop>Switzerland</cop><pmid>37298648</pmid><orcidid>https://orcid.org/0000-0002-9552-7141</orcidid><orcidid>https://orcid.org/0000-0002-5684-8188</orcidid><orcidid>https://orcid.org/0000-0002-5463-0169</orcidid><orcidid>https://orcid.org/0000-0003-3614-560X</orcidid><orcidid>https://orcid.org/0000-0003-3413-0180</orcidid><orcidid>https://orcid.org/0000-0002-8571-4197</orcidid><orcidid>https://orcid.org/0000-0002-3231-5838</orcidid></addata></record> |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| title | Intramolecular Hydrogen Bonding in N 6 -Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy |
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