Residue‐ and Sequence‐Selective Binding of Nonaromatic Dipeptides by Bis(β‐cyclodextrin) with a Functional Tether

Peptide recognition by synthetic receptors is known to mediate versatile protein±protein interactions and give specific biochemical functions. Among them, the development of cyclodextrin (CD)-based receptors for residueand sequence-selective recognition of peptides is one of the most challenging tasks, which may also lead us to deeper understanding and smarter mimicking of vital biological functions. Recent investigations have demonstrated that bis(b-CD)s linked with a short tether possess binding abilities and selectivities for specific guests much higher than native b-CD. This was made possible through the cooperative two-point recognition that mimics the highly substrate-specific binding of enzymes. Thus, a variety of bis(b-CD)s with considerable structural diversity have been prepared in order to elucidate their complexation behavior as well as the factors and mechanisms governing the multipoint recognition upon inclusion complexation by bis-CDs. However, the work on molecular recognition by bis(b-CD)s has been concentrated mostly on the complexation of rather simple organic guests and amino acids, and practically no attempt has been made on the recognition of nonaromatic oligopeptides by bis(b-CD)s, outside the elegant work on oligopeptides carrying two aromatic amino acid residues for a simultaneous complexation by CD cavities and on testing a library of aromatic and nonaromatic tripeptides for binding to a bisas well as a mono-CD receptor. Here, we report the unique molecular-recognition behavior of a newly synthesized dithiobenzoylamino-bridged bis(b-CD) (1) with representative nonaromatic dipeptides and the remarkable fluorescence enhancement by coinclusion of a dipeptide guest with the tether moiety into the cavity.

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