Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs.

Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs. Research Abstract Details 

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Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs. Abstract Text:

Green fluorescent protein (GFP) and homologous proteins possess a unique pathway of chromophore formation based on autocatalytic modification of their own amino acid residues. Green-to-red photoconvertible fluorescent protein Kaede carries His-Tyr-Gly chromophore-forming triad. Here, we describe synthesis of Kaede red chromophore (2-[(1E)-2-(5-imidazolyl)ethenyl]-4-(p-hydroxybenzylidene)-5-imidazolone) and its analogs that can be potentially formed by natural amino acid residues. Chromophores corresponding to the following tripeptides were obtained: His-Tyr-Gly, Trp-Tyr-Gly, Phe-Trp-Gly, Tyr-Trp-Gly, Asn-Tyr-Gly, Phe-Tyr-Gly, and Tyr-Tyr-Gly. In basic conditions they fluoresced red with relatively high quantum yield (up to 0.017 for Trp-derived compounds). The most red-shifted absorption peak at 595nm was found for the chromophore Trp-Tyr-Gly in basic DMSO. Surprisingly, in basic DMF non-aromatic Asn-derived chromophore Asn-Tyr-Gly demonstrated the most red-shifted emission maximum at 642nm. Thus, Asn residue may be a promising substituent, which can potentially diversify posttranslational chemistry in GFP-like proteins.

Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs. Publishing Authors By Initials

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Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Bioorganic chemistry

VOLUME: 36

Page Numbers: 96-104

Journal Abbreviation: Bioorg. Chem.

ISSN: 0045-2068

DAY: 11

MONTH: 02

YEAR: 2008

Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs. Information

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LANGUAGE: eng

NlmUniqueID: 1303703

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Grant and Affiliation Information for Synthesis and properties of the red chromophore of the green-to-red photoconvertible fluorescent protein Kaede and its analogs.

AFFILIATION: Institute of Bioorganic Chemistry, Lab of Molecular Techonologies, Miklukho-Maklaya 16/10, Moscow 117997, Russian Federation.

Country: United States

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MEDLINETA: Bioorg Chem

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