Molecular-recognition properties of a water-soluble ...

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Title Molecular-recognition properties of a water-soluble cucurbit[6]uril analogue
Author(s) J. Lagona, Brian D. Wagner, L. Isaacs
Journal The Journal of Organic Chemistry
Date 2006
Volume 71
Issue 3
Start page 1181
End page 1190
Abstract Abstract: The molecular-recognition properties of the cucurbit[6]uril analogue (1) in aqueous buffer (sodium acetate, 50 mM, pH 4.74, 25 C) toward a variety of guests including alkanediamines (6-12), aromatics (14-32), amino acids (33-36), and nucleobases (37-42) were studied by fluorescence spectroscopy. For the alkanediamines studied (H2N(CH)nNH2, n = 6, 7, 8, 9, 10, 11, 12), the association constants increase as the length of the alkane (n) is increased. Host 1 is capable of forming strong complexes with guests containing aromatic rings with association constants (Ka) ranging from 102 to 106 M-1 as a result of the favorable - interactions that occur between host 1 and the aromatic rings of the guest when bound in the cavity of 1. Biologically relevant guests such as amino acids and nucleobases are also bound in the cavity of 1 with Ka values ranging from 103 to 106 M-1. Consequently, cucurbit[6]uril analogue 1 functions as a versatile fluorescent sensor for the presence of a wide range of chemically and biologically important substances in aqueous solution including nitroaromatics, neurotransmitters, amino acids, and nucleobases.
DOI 10.1021/jo052294i

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