Design, Synthesis, and Screening of a Library of Peptidyl Bis(BoroxoIes) as Oligosaccharide Receptors in Water: Identification of a Receptor for the Tumor Marker TF-Antigen Disaccharide

摘要

The important challenge of carbohydrate recognition in water presents several exciting opportunities in chemical biology and medicine, with potential applications in the analysis, purification, diagnostic, and physiological control of biologically important glycans. Although a number of synthetic receptors have been described for the recognition of complex carbohydrates in organic solvents, it is notoriously difficult to achieve the same efficiency under physiological conditions (i.e., water at neutral pH). The essence of the problem lies in the competition between the multiple hydroxy groups on the carbohydrates and the overwhelming ones from the bulk solvent, water. Recently, Davis and co-workers described a water-soluble, complex cage-like receptor that displayed low millimolar affinity and high selectivity for a distinct disaccharide in neutral water.