The effect of oxidation on the electronic structure of the green fluorescent protein chromophore
Electronic structure calculations of the singly and doubly ionized states of deprotonated 4 ′ -hydroxybenzylidene-2,3-dimethylimidazolinone (HBDI anion) are presented. One-electron oxidation produces a doublet radical that has blueshifted absorption, whereas the detachment of two electrons yields a...
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| Veröffentlicht in: | The Journal of chemical physics 2010-03, Vol.132 (11), p.115104-115104-9 |
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| container_end_page | 115104-9 |
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| container_issue | 11 |
| container_start_page | 115104 |
| container_title | The Journal of chemical physics |
| container_volume | 132 |
| creator | Epifanovsky, E. Polyakov, I. Grigorenko, B. Nemukhin, A. Krylov, A. I. |
| description | Electronic structure calculations of the singly and doubly ionized states of deprotonated
4
′
-hydroxybenzylidene-2,3-dimethylimidazolinone (HBDI anion) are presented. One-electron oxidation produces a doublet radical that has blueshifted absorption, whereas the detachment of two electrons yields a closed-shell cation with strongly redshifted (by about 0.6 eV) absorption relative to the HBDI anion. The results suggest that the doubly oxidized species may be responsible for oxidative redding of green fluorescent protein. The proposed mechanism involves two-step oxidation via electronically excited states and is consistent with the available experimental information [
A. M. Bogdanov
,
A. S. Mishin
,
I. V. Yampolsky
,
,
Nat. Chem. Biol.
5
,
459
(
2009
)
]. The spectroscopic signatures of the ionization-induced structural changes in the chromophore are also discussed. |
| doi_str_mv | 10.1063/1.3336425 |
| format | Article |
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4
′
-hydroxybenzylidene-2,3-dimethylimidazolinone (HBDI anion) are presented. One-electron oxidation produces a doublet radical that has blueshifted absorption, whereas the detachment of two electrons yields a closed-shell cation with strongly redshifted (by about 0.6 eV) absorption relative to the HBDI anion. The results suggest that the doubly oxidized species may be responsible for oxidative redding of green fluorescent protein. The proposed mechanism involves two-step oxidation via electronically excited states and is consistent with the available experimental information [
A. M. Bogdanov
,
A. S. Mishin
,
I. V. Yampolsky
,
,
Nat. Chem. Biol.
5
,
459
(
2009
)
]. The spectroscopic signatures of the ionization-induced structural changes in the chromophore are also discussed.</description><identifier>ISSN: 0021-9606</identifier><identifier>EISSN: 1089-7690</identifier><identifier>DOI: 10.1063/1.3336425</identifier><identifier>PMID: 20331319</identifier><identifier>CODEN: JCPSA6</identifier><language>eng</language><publisher>United States: American Institute of Physics</publisher><subject>Electrons ; Green Fluorescent Proteins - chemistry ; Imidazolines - chemistry ; Molecular Dynamics Simulation ; Molecular Structure ; Oxidation-Reduction ; Quantum Theory</subject><ispartof>The Journal of chemical physics, 2010-03, Vol.132 (11), p.115104-115104-9</ispartof><rights>2010 American Institute of Physics</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-25c9a918cb0cc9cee521d129465b2d85928dd5b1a4595501dc42693730718d6f3</citedby><cites>FETCH-LOGICAL-c405t-25c9a918cb0cc9cee521d129465b2d85928dd5b1a4595501dc42693730718d6f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,794,1559,4512,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20331319$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Epifanovsky, E.</creatorcontrib><creatorcontrib>Polyakov, I.</creatorcontrib><creatorcontrib>Grigorenko, B.</creatorcontrib><creatorcontrib>Nemukhin, A.</creatorcontrib><creatorcontrib>Krylov, A. I.</creatorcontrib><title>The effect of oxidation on the electronic structure of the green fluorescent protein chromophore</title><title>The Journal of chemical physics</title><addtitle>J Chem Phys</addtitle><description>Electronic structure calculations of the singly and doubly ionized states of deprotonated
4
′
-hydroxybenzylidene-2,3-dimethylimidazolinone (HBDI anion) are presented. One-electron oxidation produces a doublet radical that has blueshifted absorption, whereas the detachment of two electrons yields a closed-shell cation with strongly redshifted (by about 0.6 eV) absorption relative to the HBDI anion. The results suggest that the doubly oxidized species may be responsible for oxidative redding of green fluorescent protein. The proposed mechanism involves two-step oxidation via electronically excited states and is consistent with the available experimental information [
A. M. Bogdanov
,
A. S. Mishin
,
I. V. Yampolsky
,
,
Nat. Chem. Biol.
5
,
459
(
2009
)
]. The spectroscopic signatures of the ionization-induced structural changes in the chromophore are also discussed.</description><subject>Electrons</subject><subject>Green Fluorescent Proteins - chemistry</subject><subject>Imidazolines - chemistry</subject><subject>Molecular Dynamics Simulation</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Quantum Theory</subject><issn>0021-9606</issn><issn>1089-7690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMtKxDAUhoMozji68AUkO3HRMZcmbTaCDN5gwM24jm0uTqVtxiQFfXtTO7oTDpzF__FzzgfAOUZLjDi9xktKKc8JOwBzjEqRFVygQzBHiOBMcMRn4CSEd4QQLkh-DGYEUYopFnPwutkaaKw1KkJnoftsdBUb18M0cYzalHjXNwqG6AcVB29GcMzevDE9tO3gvAnK9BHuvIum6aHaete53TYFp-DIVm0wZ_u9AC_3d5vVY7Z-fnha3a4zlSMWM8KUqAQuVY2UEsoYRrDGROSc1USXTJBSa1bjKmeCMYS1ygkXtKCowKXmli7A5dSbbvgYTIiya9JRbVv1xg1BFpQSUfL0-AJcTaTyLgRvrNz5pqv8l8RIjj4llnufib3Ytw51Z_Qf-SswATcTEFQTf8z935ZUy0m1dFZOquk31nyFRA</recordid><startdate>20100321</startdate><enddate>20100321</enddate><creator>Epifanovsky, E.</creator><creator>Polyakov, I.</creator><creator>Grigorenko, B.</creator><creator>Nemukhin, A.</creator><creator>Krylov, A. I.</creator><general>American Institute of Physics</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>20100321</creationdate><title>The effect of oxidation on the electronic structure of the green fluorescent protein chromophore</title><author>Epifanovsky, E. ; Polyakov, I. ; Grigorenko, B. ; Nemukhin, A. ; Krylov, A. I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-25c9a918cb0cc9cee521d129465b2d85928dd5b1a4595501dc42693730718d6f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Electrons</topic><topic>Green Fluorescent Proteins - chemistry</topic><topic>Imidazolines - chemistry</topic><topic>Molecular Dynamics Simulation</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Quantum Theory</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Epifanovsky, E.</creatorcontrib><creatorcontrib>Polyakov, I.</creatorcontrib><creatorcontrib>Grigorenko, B.</creatorcontrib><creatorcontrib>Nemukhin, A.</creatorcontrib><creatorcontrib>Krylov, A. I.</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>The Journal of chemical physics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Epifanovsky, E.</au><au>Polyakov, I.</au><au>Grigorenko, B.</au><au>Nemukhin, A.</au><au>Krylov, A. I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The effect of oxidation on the electronic structure of the green fluorescent protein chromophore</atitle><jtitle>The Journal of chemical physics</jtitle><addtitle>J Chem Phys</addtitle><date>2010-03-21</date><risdate>2010</risdate><volume>132</volume><issue>11</issue><spage>115104</spage><epage>115104-9</epage><pages>115104-115104-9</pages><issn>0021-9606</issn><eissn>1089-7690</eissn><coden>JCPSA6</coden><abstract>Electronic structure calculations of the singly and doubly ionized states of deprotonated
4
′
-hydroxybenzylidene-2,3-dimethylimidazolinone (HBDI anion) are presented. One-electron oxidation produces a doublet radical that has blueshifted absorption, whereas the detachment of two electrons yields a closed-shell cation with strongly redshifted (by about 0.6 eV) absorption relative to the HBDI anion. The results suggest that the doubly oxidized species may be responsible for oxidative redding of green fluorescent protein. The proposed mechanism involves two-step oxidation via electronically excited states and is consistent with the available experimental information [
A. M. Bogdanov
,
A. S. Mishin
,
I. V. Yampolsky
,
,
Nat. Chem. Biol.
5
,
459
(
2009
)
]. The spectroscopic signatures of the ionization-induced structural changes in the chromophore are also discussed.</abstract><cop>United States</cop><pub>American Institute of Physics</pub><pmid>20331319</pmid><doi>10.1063/1.3336425</doi><tpages>1</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-9606 |
| ispartof | The Journal of chemical physics, 2010-03, Vol.132 (11), p.115104-115104-9 |
| issn | 0021-9606 1089-7690 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733298603 |
| source | MEDLINE; AIP Journals Complete; AIP Digital Archive; Alma/SFX Local Collection |
| subjects | Electrons Green Fluorescent Proteins - chemistry Imidazolines - chemistry Molecular Dynamics Simulation Molecular Structure Oxidation-Reduction Quantum Theory |
| title | The effect of oxidation on the electronic structure of the green fluorescent protein chromophore |
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