Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine—Formation of cyclic adducts
Acrolein forms two cyclic adducts with the adenine base in aqueous solutions. One adduct is an unstable acetal consisting of two condensed rings derived from two units of acrolein. Treatment of 2′-deoxyadenosine with acrolein at pH 4.6 in 37 °C affords unstable adducts containing either one or two f...
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| Veröffentlicht in: | Bioorganic chemistry 2006-02, Vol.34 (1), p.39-48 |
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| creator | Pawłowicz, Agnieszka J. Munter, Tony Klika, Karel D. Kronberg, Leif |
| description | Acrolein forms two cyclic adducts with the adenine base in aqueous solutions. One adduct is an unstable acetal consisting of two condensed rings derived from two units of acrolein.
Treatment of 2′-deoxyadenosine with acrolein at pH 4.6 in 37
°C affords unstable adducts containing either one or two fused ring systems where the hydroxypropano units are derived from acrolein. Since the use of 2′-deoxyadenosine resulted in the creation of at least four diastereoisomers for the adduct made up of two fused rings, therefore, for identification and assignment of the products, 9-ethyladenine was used instead as the starting material in the reaction. The products,
3
E
and
4
E
, were structurally characterised by UV, mass spectrometry and NMR spectroscopy. |
| doi_str_mv | 10.1016/j.bioorg.2005.10.006 |
| format | Article |
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Treatment of 2′-deoxyadenosine with acrolein at pH 4.6 in 37
°C affords unstable adducts containing either one or two fused ring systems where the hydroxypropano units are derived from acrolein. Since the use of 2′-deoxyadenosine resulted in the creation of at least four diastereoisomers for the adduct made up of two fused rings, therefore, for identification and assignment of the products, 9-ethyladenine was used instead as the starting material in the reaction. The products,
3
E
and
4
E
, were structurally characterised by UV, mass spectrometry and NMR spectroscopy.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2005.10.006</identifier><identifier>PMID: 16343591</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>2′-Deoxyadenosine adducts ; 9-Ethyladenine ; Acrolein ; Acrolein - chemistry ; Adenine - analogs & derivatives ; Adenine - chemistry ; Bicyclic adduct ; Deoxyadenosines - chemistry ; DNA Adducts - chemistry ; Hydrogen-Ion Concentration ; Models, Chemical ; Spectrum Analysis ; Stereochemistry ; Stereoisomerism ; Structural assignment</subject><ispartof>Bioorganic chemistry, 2006-02, Vol.34 (1), p.39-48</ispartof><rights>2005 Elsevier Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-e7d7be4b3f2802b9cfadcf03338f71596d678166839acea02aba7b08f084f2673</citedby><cites>FETCH-LOGICAL-c391t-e7d7be4b3f2802b9cfadcf03338f71596d678166839acea02aba7b08f084f2673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bioorg.2005.10.006$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16343591$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pawłowicz, Agnieszka J.</creatorcontrib><creatorcontrib>Munter, Tony</creatorcontrib><creatorcontrib>Klika, Karel D.</creatorcontrib><creatorcontrib>Kronberg, Leif</creatorcontrib><title>Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine—Formation of cyclic adducts</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>Acrolein forms two cyclic adducts with the adenine base in aqueous solutions. One adduct is an unstable acetal consisting of two condensed rings derived from two units of acrolein.
Treatment of 2′-deoxyadenosine with acrolein at pH 4.6 in 37
°C affords unstable adducts containing either one or two fused ring systems where the hydroxypropano units are derived from acrolein. Since the use of 2′-deoxyadenosine resulted in the creation of at least four diastereoisomers for the adduct made up of two fused rings, therefore, for identification and assignment of the products, 9-ethyladenine was used instead as the starting material in the reaction. The products,
3
E
and
4
E
, were structurally characterised by UV, mass spectrometry and NMR spectroscopy.</description><subject>2′-Deoxyadenosine adducts</subject><subject>9-Ethyladenine</subject><subject>Acrolein</subject><subject>Acrolein - chemistry</subject><subject>Adenine - analogs & derivatives</subject><subject>Adenine - chemistry</subject><subject>Bicyclic adduct</subject><subject>Deoxyadenosines - chemistry</subject><subject>DNA Adducts - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Models, Chemical</subject><subject>Spectrum Analysis</subject><subject>Stereochemistry</subject><subject>Stereoisomerism</subject><subject>Structural assignment</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM1KxDAUhYMoOv68gUhX7jreJG3abAQR_0AQRLeGNLnRDJ1Gk446Ox_CJ_GRfBI7zIg7VxcO55zL-QjZpzCmQMXRZNz4EOLjmAGUgzQGEGtkREFCziiDdTICKMqcgai3yHZKEwBKi0pski0qeMFLSUfk4Ra16X3osuAybWJo0XfZm--fMvb98ZVbDO9zbbELyXeY6c5mMsf-ad4uxEH6_vg8D3GqfzvM3LTeZNramenTLtlwuk24t7o75P787O70Mr--ubg6PbnODZe0z7GyVYNFwx2rgTXSOG2NA8557SpaSmFFVVMhai61QQ1MN7pqoHZQF46Jiu-Qw2XvcwwvM0y9mvpksG11h2GWFJVVyQTIwVgsjcPUlCI69Rz9VMe5oqAWXNVELbmqBdeFOnAdYger_lkzRfsXWoEcDMdLAw4rXz1GlYzHzqD1EU2vbPD_f_gBgRmN7A</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>Pawłowicz, Agnieszka J.</creator><creator>Munter, Tony</creator><creator>Klika, Karel D.</creator><creator>Kronberg, Leif</creator><general>Elsevier Inc</general><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>7TM</scope></search><sort><creationdate>20060201</creationdate><title>Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine—Formation of cyclic adducts</title><author>Pawłowicz, Agnieszka J. ; Munter, Tony ; Klika, Karel D. ; Kronberg, Leif</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-e7d7be4b3f2802b9cfadcf03338f71596d678166839acea02aba7b08f084f2673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>2′-Deoxyadenosine adducts</topic><topic>9-Ethyladenine</topic><topic>Acrolein</topic><topic>Acrolein - chemistry</topic><topic>Adenine - analogs & derivatives</topic><topic>Adenine - chemistry</topic><topic>Bicyclic adduct</topic><topic>Deoxyadenosines - chemistry</topic><topic>DNA Adducts - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Models, Chemical</topic><topic>Spectrum Analysis</topic><topic>Stereochemistry</topic><topic>Stereoisomerism</topic><topic>Structural assignment</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pawłowicz, Agnieszka J.</creatorcontrib><creatorcontrib>Munter, Tony</creatorcontrib><creatorcontrib>Klika, Karel D.</creatorcontrib><creatorcontrib>Kronberg, Leif</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><jtitle>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pawłowicz, Agnieszka J.</au><au>Munter, Tony</au><au>Klika, Karel D.</au><au>Kronberg, Leif</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine—Formation of cyclic adducts</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2006-02-01</date><risdate>2006</risdate><volume>34</volume><issue>1</issue><spage>39</spage><epage>48</epage><pages>39-48</pages><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>Acrolein forms two cyclic adducts with the adenine base in aqueous solutions. One adduct is an unstable acetal consisting of two condensed rings derived from two units of acrolein.
Treatment of 2′-deoxyadenosine with acrolein at pH 4.6 in 37
°C affords unstable adducts containing either one or two fused ring systems where the hydroxypropano units are derived from acrolein. Since the use of 2′-deoxyadenosine resulted in the creation of at least four diastereoisomers for the adduct made up of two fused rings, therefore, for identification and assignment of the products, 9-ethyladenine was used instead as the starting material in the reaction. The products,
3
E
and
4
E
, were structurally characterised by UV, mass spectrometry and NMR spectroscopy.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>16343591</pmid><doi>10.1016/j.bioorg.2005.10.006</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0045-2068 |
| ispartof | Bioorganic chemistry, 2006-02, Vol.34 (1), p.39-48 |
| issn | 0045-2068 1090-2120 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_19752609 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 2′-Deoxyadenosine adducts 9-Ethyladenine Acrolein Acrolein - chemistry Adenine - analogs & derivatives Adenine - chemistry Bicyclic adduct Deoxyadenosines - chemistry DNA Adducts - chemistry Hydrogen-Ion Concentration Models, Chemical Spectrum Analysis Stereochemistry Stereoisomerism Structural assignment |
| title | Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine—Formation of cyclic adducts |
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