Steric and Electronic Effects in Capsule-Confined Green Fluorescent Protein Chromophores
The turn-on of emission in fluorescent protein chromophores sequestered in an “octaacid” capsule is controlled by stereoelectronic effects described by a linear free energy relationship. The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the ele...
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| Veröffentlicht in: | Journal of the American Chemical Society 2011-02, Vol.133 (4), p.712-715 |
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| container_end_page | 715 |
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| container_issue | 4 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 133 |
| creator | Baldridge, Anthony Samanta, Shampa R Jayaraj, Nithyanandhan Ramamurthy, V Tolbert, Laren M |
| description | The turn-on of emission in fluorescent protein chromophores sequestered in an “octaacid” capsule is controlled by stereoelectronic effects described by a linear free energy relationship. The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the electronic effects, including ortho effects, can be treated with Hammett σ parameters. The use of substituent volumes rather than A values reflects packing of the molecule within the confines of the capsule. |
| doi_str_mv | 10.1021/ja1094606 |
| format | Article |
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The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the electronic effects, including ortho effects, can be treated with Hammett σ parameters. 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The use of substituent volumes rather than A values reflects packing of the molecule within the confines of the capsule.</description><subject>Benzylidene Compounds - chemistry</subject><subject>Capsules</subject><subject>Color</subject><subject>Electrons</subject><subject>Green Fluorescent Proteins - chemistry</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Imidazoles - chemistry</subject><subject>Spectrometry, Fluorescence</subject><subject>Stereoisomerism</subject><subject>Thermodynamics</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE9Lw0AQxRdRbK0e_AKSi4iH6P5LdnOU0FahoKCCt7DdnaUpyW7dTQ5-exNae_IyM4_58Zh5CF0T_EAwJY9bRXDBc5yfoCnJKE4zQvNTNMUY01TInE3QRYzbQXIqyTmaUEIE5ySboq_3DkKtE-VMMm9Ad8G7Qc6tHeaY1C4p1S72DaSld7Z2YJJlAHDJoul9gKjBdclb8B2M6Cb41u824-ISnVnVRLg69Bn6XMw_yud09bp8KZ9WqWKEdylIbgRVogCp8oLQNRPAxloUxgrJNAWRidwIIQ1omVujFaYF03ItrNWMzdDd3ncX_HcPsavaeriqaZQD38dKcsko5XQk7_ekDj7GALbahbpV4aciuBpzrI45DuzNwbVft2CO5F9wA3C7B5SO1db3wQ1P_mP0CyR3eRc</recordid><startdate>20110202</startdate><enddate>20110202</enddate><creator>Baldridge, Anthony</creator><creator>Samanta, Shampa R</creator><creator>Jayaraj, Nithyanandhan</creator><creator>Ramamurthy, V</creator><creator>Tolbert, Laren M</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>20110202</creationdate><title>Steric and Electronic Effects in Capsule-Confined Green Fluorescent Protein Chromophores</title><author>Baldridge, Anthony ; Samanta, Shampa R ; Jayaraj, Nithyanandhan ; Ramamurthy, V ; Tolbert, Laren M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-e84d72a79e8a6912b37e32b3799df783c2e7576d778dec86fdca0293c8b7ffc33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Benzylidene Compounds - chemistry</topic><topic>Capsules</topic><topic>Color</topic><topic>Electrons</topic><topic>Green Fluorescent Proteins - chemistry</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Imidazoles - chemistry</topic><topic>Spectrometry, Fluorescence</topic><topic>Stereoisomerism</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Baldridge, Anthony</creatorcontrib><creatorcontrib>Samanta, Shampa R</creatorcontrib><creatorcontrib>Jayaraj, Nithyanandhan</creatorcontrib><creatorcontrib>Ramamurthy, V</creatorcontrib><creatorcontrib>Tolbert, Laren M</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>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Baldridge, Anthony</au><au>Samanta, Shampa R</au><au>Jayaraj, Nithyanandhan</au><au>Ramamurthy, V</au><au>Tolbert, Laren M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Steric and Electronic Effects in Capsule-Confined Green Fluorescent Protein Chromophores</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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| ispartof | Journal of the American Chemical Society, 2011-02, Vol.133 (4), p.712-715 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Benzylidene Compounds - chemistry Capsules Color Electrons Green Fluorescent Proteins - chemistry Hydrophobic and Hydrophilic Interactions Imidazoles - chemistry Spectrometry, Fluorescence Stereoisomerism Thermodynamics |
| title | Steric and Electronic Effects in Capsule-Confined Green Fluorescent Protein Chromophores |
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