Inclusion by β-cyclodextrin of a pyrene-labeled dipeptide photoprobe

An alanyltryptophan dipeptide ( 1 ), labeled at the N-terminus with a pyrene moiety is bound strongly by β-cyclodextrin in water, leading to enhancement of the fluorescence of the photoprobe. The effect is ascribed to restriction of conformational freedom for the dipeptide and a consequent reduction...

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Bibliographic Details
Published in:Tetrahedron letters 2002-08, Vol.43 (34), p.6079-6082
Main Authors: Jones, Guilford, Zhou, Xin, Lu, LilyN
Format: Article
Language:English
Subjects:
cyclodextrin–peptide complex
peptide electron transfer
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Summary:An alanyltryptophan dipeptide ( 1 ), labeled at the N-terminus with a pyrene moiety is bound strongly by β-cyclodextrin in water, leading to enhancement of the fluorescence of the photoprobe. The effect is ascribed to restriction of conformational freedom for the dipeptide and a consequent reduction in the rate of intramolecular electron transfer that occurs between pyrene and Trp/indole moieties. The Pyr-Ala-TrpOEt (carbon atoms in blue):β-CD(carbon atoms in gray) complex.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01280-7