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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
27
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pubmed:dateCreated |
2010-7-7
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pubmed:abstractText |
We report the results of a multidisciplinary research effort where the methods of computational photochemistry and retrosynthetic analysis/synthesis have contributed to the preparation of a novel N-alkylated indanylidene-pyrroline Schiff base featuring an exocyclic double bond and a permanent zwitterionic head. We show that, due to its large dipole moment and efficient photoisomerization, such a system may constitute the prototype of a novel generation of electrostatic switches achieving a reversible light-induced dipole moment change on the order of 30 D. The modeling of a peptide fragment incorporating the zwitterionic head into a conformationally rigid side chain shows that the switch can effectively modulate the fluorescence of a tryptophan probe.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Jul
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pubmed:issn |
1520-5126
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pubmed:author |
pubmed-author:BasosiRiccardoR,
pubmed-author:DingWan JianWJ,
pubmed-author:EOO,
pubmed-author:FerréNicolasN,
pubmed-author:FrutosLuis ManuelLM,
pubmed-author:FusiStefaniaS,
pubmed-author:LatteriniLoredanaL,
pubmed-author:MartinElenaE,
pubmed-author:MelloniAlfonsoA,
pubmed-author:OlivucciMassimoM,
pubmed-author:ParisiMaria LauraML,
pubmed-author:Rossi PaccaniRiccardoR,
pubmed-author:RyazantsevMikhailM,
pubmed-author:SinicropiAdalgisaA,
pubmed-author:ZaniratoVinicioV
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pubmed:issnType |
Electronic
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pubmed:day |
14
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pubmed:volume |
132
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
9310-9
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pubmed:meshHeading |
pubmed-meshheading:20568762-Fluorescence,
pubmed-meshheading:20568762-Isomerism,
pubmed-meshheading:20568762-Light,
pubmed-meshheading:20568762-Models, Molecular,
pubmed-meshheading:20568762-Molecular Probes,
pubmed-meshheading:20568762-Peptide Fragments,
pubmed-meshheading:20568762-Photochemical Processes,
pubmed-meshheading:20568762-Protein Conformation,
pubmed-meshheading:20568762-Schiff Bases,
pubmed-meshheading:20568762-Static Electricity,
pubmed-meshheading:20568762-Tryptophan
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pubmed:year |
2010
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pubmed:articleTitle |
Modeling, preparation, and characterization of a dipole moment switch driven by Z/E photoisomerization.
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pubmed:affiliation |
Dipartimento di Chimica, Università degli Studi di Siena, via Aldo Moro 2, I-53100 Siena, Italy.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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