Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine
The photoreaction of 5-methoxypsoralen (5-MOP) with thymidine as a DNA model compound was investigated under dry-state conditions. In this respect, a thin film of thymidine and 5-MOP in a ratio 10:1 was exposed to 350-nm UV light. Four [2 + 2] photocycloadducts were isolated in a 0.5-2.2% yield with...
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| Veröffentlicht in: | Chemical research in toxicology 1993-11, Vol.6 (6), p.858-865 |
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| creator | Anselmino, Catherine Voituriez, Lucienne Cadet, Jean |
| description | The photoreaction of 5-methoxypsoralen (5-MOP) with thymidine as a DNA model compound was investigated under dry-state conditions. In this respect, a thin film of thymidine and 5-MOP in a ratio 10:1 was exposed to 350-nm UV light. Four [2 + 2] photocycloadducts were isolated in a 0.5-2.2% yield with respect to 5-MOP by HPLC and characterized as two pairs of cis-syn and cis-anti diastereoisomers, respectively, on the basis of extensive spectroscopic measurements, including UV, fast atom bombardment mass spectrometry, 1H and 13C NMR, and CD. Information concerning the absolute configuration of the four photocycloadducts was inferred from detailed nuclear Overhauser enhancement experiments. This is indicative of a 3R,4S,5R,6S and a 3S,4R,5S,6R configuration for the cis-anti cycloadducts and a 3S,4R,5R,6S) and a 3R,4S,5S,6R configuration for the cis-syn cycloadducts. In addition, conformational features of the four photocycloadducts were obtained from consideration of various 1H NMR measurements including NOE data. |
| doi_str_mv | 10.1021/tx00036a016 |
| format | Article |
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In this respect, a thin film of thymidine and 5-MOP in a ratio 10:1 was exposed to 350-nm UV light. Four [2 + 2] photocycloadducts were isolated in a 0.5-2.2% yield with respect to 5-MOP by HPLC and characterized as two pairs of cis-syn and cis-anti diastereoisomers, respectively, on the basis of extensive spectroscopic measurements, including UV, fast atom bombardment mass spectrometry, 1H and 13C NMR, and CD. Information concerning the absolute configuration of the four photocycloadducts was inferred from detailed nuclear Overhauser enhancement experiments. This is indicative of a 3R,4S,5R,6S and a 3S,4R,5S,6R configuration for the cis-anti cycloadducts and a 3S,4R,5R,6S) and a 3R,4S,5S,6R configuration for the cis-syn cycloadducts. In addition, conformational features of the four photocycloadducts were obtained from consideration of various 1H NMR measurements including NOE data.</description><identifier>ISSN: 0893-228X</identifier><identifier>EISSN: 1520-5010</identifier><identifier>DOI: 10.1021/tx00036a016</identifier><identifier>PMID: 8117925</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Chromatography, High Pressure Liquid ; Circular Dichroism ; Magnetic Resonance Spectroscopy ; Medical sciences ; Methoxsalen - analogs & derivatives ; Methoxsalen - chemistry ; Pharmacology. 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Res. Toxicol</addtitle><description>The photoreaction of 5-methoxypsoralen (5-MOP) with thymidine as a DNA model compound was investigated under dry-state conditions. In this respect, a thin film of thymidine and 5-MOP in a ratio 10:1 was exposed to 350-nm UV light. Four [2 + 2] photocycloadducts were isolated in a 0.5-2.2% yield with respect to 5-MOP by HPLC and characterized as two pairs of cis-syn and cis-anti diastereoisomers, respectively, on the basis of extensive spectroscopic measurements, including UV, fast atom bombardment mass spectrometry, 1H and 13C NMR, and CD. Information concerning the absolute configuration of the four photocycloadducts was inferred from detailed nuclear Overhauser enhancement experiments. This is indicative of a 3R,4S,5R,6S and a 3S,4R,5S,6R configuration for the cis-anti cycloadducts and a 3S,4R,5R,6S) and a 3R,4S,5S,6R configuration for the cis-syn cycloadducts. In addition, conformational features of the four photocycloadducts were obtained from consideration of various 1H NMR measurements including NOE data.</description><subject>Biological and medical sciences</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Circular Dichroism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Methoxsalen - analogs & derivatives</subject><subject>Methoxsalen - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Photochemistry</subject><subject>Skin, nail, hair, dermoskeleton</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Stereoisomerism</subject><subject>Thymidine - chemistry</subject><subject>Thymidine - radiation effects</subject><subject>Ultraviolet Rays</subject><issn>0893-228X</issn><issn>1520-5010</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c-LEzEUB_AgylpXT56FOYgeZPQl6SQzR62uCgsqFvQWXvODZp1JuskMdMQ_3tSW4kHwlMD75JH3voQ8pvCSAqOvxj0AcIFAxR2yoA2DugEKd8kC2o7XjLXf75MHOd8A0PJAXpCLllLZsWZBfq22mFCPNvmfOPoYquiqcWsr7XOd51BhMH_uGEZfGY-5UBt9joNN-YCberDjNu7nXY4Jexuq3ZxisHX2xlZDDFHPuo9ozKTHXI2xtJ8Hb3ywD8k9h322j07nJVlfvVuvPtTXn95_XL2-rnFJl2PtuNQCqaO8Ew5aLp0Bx3i3QWaMsyChk1wYKZxDQTXdSNCw1BvHilx2_JI8O7bdpXg72TyqwWdt-x6DjVNWUjAum5b-F1LRctaBLPDFEeoUc07WqV3yA6ZZUVCHTNRfmRT95NR22gzWnO0phFJ_eqpj1ti7hKFs_Mx4yzl0rLD6yHzJYH8uY_qhhCwDqPXnr-pq_eXtm2-dVIexnx896qxu4pRC2fE_P_gb0WuyQQ</recordid><startdate>19931101</startdate><enddate>19931101</enddate><creator>Anselmino, Catherine</creator><creator>Voituriez, Lucienne</creator><creator>Cadet, Jean</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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>7U7</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>19931101</creationdate><title>Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine</title><author>Anselmino, Catherine ; Voituriez, Lucienne ; Cadet, Jean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-f37c6a1f1396f0837fd0f239ba2ddfe0709736d76ffa61c1b70c04cbf27fd493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Circular Dichroism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Methoxsalen - analogs & derivatives</topic><topic>Methoxsalen - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Photochemistry</topic><topic>Skin, nail, hair, dermoskeleton</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Stereoisomerism</topic><topic>Thymidine - chemistry</topic><topic>Thymidine - radiation effects</topic><topic>Ultraviolet Rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Anselmino, Catherine</creatorcontrib><creatorcontrib>Voituriez, Lucienne</creatorcontrib><creatorcontrib>Cadet, Jean</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical research in toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Anselmino, Catherine</au><au>Voituriez, Lucienne</au><au>Cadet, Jean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine</atitle><jtitle>Chemical research in toxicology</jtitle><addtitle>Chem. Res. Toxicol</addtitle><date>1993-11-01</date><risdate>1993</risdate><volume>6</volume><issue>6</issue><spage>858</spage><epage>865</epage><pages>858-865</pages><issn>0893-228X</issn><eissn>1520-5010</eissn><abstract>The photoreaction of 5-methoxypsoralen (5-MOP) with thymidine as a DNA model compound was investigated under dry-state conditions. In this respect, a thin film of thymidine and 5-MOP in a ratio 10:1 was exposed to 350-nm UV light. Four [2 + 2] photocycloadducts were isolated in a 0.5-2.2% yield with respect to 5-MOP by HPLC and characterized as two pairs of cis-syn and cis-anti diastereoisomers, respectively, on the basis of extensive spectroscopic measurements, including UV, fast atom bombardment mass spectrometry, 1H and 13C NMR, and CD. Information concerning the absolute configuration of the four photocycloadducts was inferred from detailed nuclear Overhauser enhancement experiments. This is indicative of a 3R,4S,5R,6S and a 3S,4R,5S,6R configuration for the cis-anti cycloadducts and a 3S,4R,5R,6S) and a 3R,4S,5S,6R configuration for the cis-syn cycloadducts. In addition, conformational features of the four photocycloadducts were obtained from consideration of various 1H NMR measurements including NOE data.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>8117925</pmid><doi>10.1021/tx00036a016</doi><tpages>8</tpages></addata></record> |
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| subjects | Biological and medical sciences Chromatography, High Pressure Liquid Circular Dichroism Magnetic Resonance Spectroscopy Medical sciences Methoxsalen - analogs & derivatives Methoxsalen - chemistry Pharmacology. Drug treatments Photochemistry Skin, nail, hair, dermoskeleton Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Ultraviolet Stereoisomerism Thymidine - chemistry Thymidine - radiation effects Ultraviolet Rays |
| title | Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine |
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