1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange
Analysis of 1H and 13C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange. The difference between these two compounds is the type of N-substitution on the quinolinium ring system...
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| Veröffentlicht in: | Journal of organic chemistry 2012-12, Vol.77 (23), p.10967-10971 |
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| container_end_page | 10971 |
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| container_issue | 23 |
| container_start_page | 10967 |
| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Evenson, William E Boden, Lauren M Muzikar, Katy A O’Leary, Daniel J |
| description | Analysis of 1H and 13C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange. The difference between these two compounds is the type of N-substitution on the quinolinium ring system (SYBR Safe, n-Pr; thiazole orange, Me). The 1H and 13C NMR resonances for both compounds were assigned on the basis of one- and two-dimensional (COSY, ROESY, HSQC, and HMBC) experiments. The preferred conformation of these compounds was computed by ab initio methods and found to be consistent with the NMR data. |
| doi_str_mv | 10.1021/jo3021659 |
| format | Article |
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The difference between these two compounds is the type of N-substitution on the quinolinium ring system (SYBR Safe, n-Pr; thiazole orange, Me). The 1H and 13C NMR resonances for both compounds were assigned on the basis of one- and two-dimensional (COSY, ROESY, HSQC, and HMBC) experiments. 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Org. Chem</addtitle><description>Analysis of 1H and 13C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange. The difference between these two compounds is the type of N-substitution on the quinolinium ring system (SYBR Safe, n-Pr; thiazole orange, Me). The 1H and 13C NMR resonances for both compounds were assigned on the basis of one- and two-dimensional (COSY, ROESY, HSQC, and HMBC) experiments. The preferred conformation of these compounds was computed by ab initio methods and found to be consistent with the NMR data.</description><subject>Benzothiazoles - chemistry</subject><subject>Carbocyanines - chemistry</subject><subject>Carbon Isotopes - chemistry</subject><subject>Chemistry</subject><subject>Coloring Agents - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Quinolines - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkUtPwkAUhSdGI4gu_ANmNiZuqvfOo48l1gcmIAngwtVk2s5ASWmx0y7w11sV5WzO5rs3OecQcolwi8Dwbl3xznwZHZE-SgaeH4E4Jn0AxjzOfN4jZ86toZOU8pT0GEcegAj7ZIIjqsuMIo_p62RGh87ly3JjysZRW9W0WRka73SZl4Y-7Iyj8_f7GZ1ra37OFqtcf1aFodNal0tzTk6sLpy52PuAvD09LuKRN54-v8TDsacZYOPJTIJGiBizQcIFRCLy0fghop-GIEUQSKlRcA7GRiJl1maJlkliI0wgSIEPyM3v321dfbTGNWqTu9QUhS5N1TqFjAcSQiFZh17t0TbZmExt63yj6536q6ADrveAdqkubBckzd2B8wNE8NmB06lT66qtyy6hQlDfE6j_CfgXdIpwpQ</recordid><startdate>20121207</startdate><enddate>20121207</enddate><creator>Evenson, William E</creator><creator>Boden, Lauren M</creator><creator>Muzikar, Katy A</creator><creator>O’Leary, Daniel J</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20121207</creationdate><title>1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange</title><author>Evenson, William E ; Boden, Lauren M ; Muzikar, Katy A ; O’Leary, Daniel J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a201t-5d50a10922f7b34094961e68116c80547755a14330ef94c2ffdba5bbf91b07c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Benzothiazoles - chemistry</topic><topic>Carbocyanines - chemistry</topic><topic>Carbon Isotopes - chemistry</topic><topic>Chemistry</topic><topic>Coloring Agents - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Quinolines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Evenson, William E</creatorcontrib><creatorcontrib>Boden, Lauren M</creatorcontrib><creatorcontrib>Muzikar, Katy A</creatorcontrib><creatorcontrib>O’Leary, Daniel J</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Evenson, William E</au><au>Boden, Lauren M</au><au>Muzikar, Katy A</au><au>O’Leary, Daniel J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-12-07</date><risdate>2012</risdate><volume>77</volume><issue>23</issue><spage>10967</spage><epage>10971</epage><pages>10967-10971</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Analysis of 1H and 13C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange. The difference between these two compounds is the type of N-substitution on the quinolinium ring system (SYBR Safe, n-Pr; thiazole orange, Me). The 1H and 13C NMR resonances for both compounds were assigned on the basis of one- and two-dimensional (COSY, ROESY, HSQC, and HMBC) experiments. 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| subjects | Benzothiazoles - chemistry Carbocyanines - chemistry Carbon Isotopes - chemistry Chemistry Coloring Agents - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Magnetic Resonance Spectroscopy Molecular Structure Organic chemistry Preparations and properties Quinolines - chemistry |
| title | 1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange |
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