DNA−Protein Cross-Linking: Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking
We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosi...
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| Veröffentlicht in: | Organic letters 2006-02, Vol.8 (4), p.681-683 |
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| container_title | Organic letters |
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| creator | Sun, Guangxing Fecko, Christopher J Nicewonger, Robert B Webb, Watt W Begley, Tadhg P |
| description | We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18−46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions. |
| doi_str_mv | 10.1021/ol052876m |
| format | Article |
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Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18−46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol052876m</identifier><identifier>PMID: 16468741</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amino Acids, Aromatic - chemistry ; Cross-Linking Reagents - chemistry ; DNA - chemistry ; Models, Biological ; Proteins - chemistry ; Pyrimidines - chemistry</subject><ispartof>Organic letters, 2006-02, Vol.8 (4), p.681-683</ispartof><rights>Copyright © 2006 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-73644d05d200810649558527181a9f802674fe3e8090492e3fb722fc02dd44113</citedby><cites>FETCH-LOGICAL-a313t-73644d05d200810649558527181a9f802674fe3e8090492e3fb722fc02dd44113</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol052876m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol052876m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16468741$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sun, Guangxing</creatorcontrib><creatorcontrib>Fecko, Christopher J</creatorcontrib><creatorcontrib>Nicewonger, Robert B</creatorcontrib><creatorcontrib>Webb, Watt W</creatorcontrib><creatorcontrib>Begley, Tadhg P</creatorcontrib><title>DNA−Protein Cross-Linking: Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18−46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.</description><subject>Amino Acids, Aromatic - chemistry</subject><subject>Cross-Linking Reagents - chemistry</subject><subject>DNA - chemistry</subject><subject>Models, Biological</subject><subject>Proteins - chemistry</subject><subject>Pyrimidines - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLtOwzAUhi0EolAYeAGUBSSGwLHjS8IWlatUoBIwhzR2kEsSFzsZujHCyiP2SXDVqgiJ6fhYnz_5_xE6wHCKgeAzUwEjseD1BtrBjESh8Pvm-syhh3admwBgf5Nsox7mlMeC4h30cnGfzj-_R9a0SjfBwBrnwqFu3nTzej7_-ArujFRV8DhzrapdUBobjGZW11rqRvmHqTV13uoiSGvdmCAttPwr2UNbZV45tb-affR8dfk0uAmHD9e3g3QY5hGO2lBEnFIJTBKAGAOnCWMxIwLHOE_KGAgXtFSRiiEBmhAVlWNBSFkAkZJSjKM-Ol56p9a8d8q1Wa1doaoqb5TpXMaFdxJGPXiyBIvFN60qs6nPk9tZhiFb1Jmt6_Ts4UrajWslf8lVfx44WgJ54bKJ6WzjM_4j-gHQS3yd</recordid><startdate>20060216</startdate><enddate>20060216</enddate><creator>Sun, Guangxing</creator><creator>Fecko, Christopher J</creator><creator>Nicewonger, Robert B</creator><creator>Webb, Watt W</creator><creator>Begley, Tadhg P</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20060216</creationdate><title>DNA−Protein Cross-Linking: Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking</title><author>Sun, Guangxing ; Fecko, Christopher J ; Nicewonger, Robert B ; Webb, Watt W ; Begley, Tadhg P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-73644d05d200810649558527181a9f802674fe3e8090492e3fb722fc02dd44113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Amino Acids, Aromatic - chemistry</topic><topic>Cross-Linking Reagents - chemistry</topic><topic>DNA - chemistry</topic><topic>Models, Biological</topic><topic>Proteins - chemistry</topic><topic>Pyrimidines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Guangxing</creatorcontrib><creatorcontrib>Fecko, Christopher J</creatorcontrib><creatorcontrib>Nicewonger, Robert B</creatorcontrib><creatorcontrib>Webb, Watt W</creatorcontrib><creatorcontrib>Begley, Tadhg P</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Guangxing</au><au>Fecko, Christopher J</au><au>Nicewonger, Robert B</au><au>Webb, Watt W</au><au>Begley, Tadhg P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DNA−Protein Cross-Linking: Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2006-02, Vol.8 (4), p.681-683 |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | Amino Acids, Aromatic - chemistry Cross-Linking Reagents - chemistry DNA - chemistry Models, Biological Proteins - chemistry Pyrimidines - chemistry |
| title | DNA−Protein Cross-Linking: Model Systems for Pyrimidine−Aromatic Amino Acid Cross-Linking |
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