Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties | Zendy

Poulami Talukder | Zendy; Shengxi Chen | Zendy; Pablo M. Arce | Zendy; Sidney M. Hecht | Zendy

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Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

Author(s) -

Poulami Talukder,

Shengxi Chen,

Pablo M. Arce,

Sidney M. Hecht

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol403429e

Subject(s) - chemistry , tryptophan , dihydrofolate reductase , fluorescence , absorption (acoustics) , stereochemistry , stokes shift , combinatorial chemistry , amino acid , biochemistry , enzyme , optics , physics

Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schöllkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

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