Chiral recognition saccharides

Competitive binding studies have shown that 164 and 166 are suitable for the detection of glucose at physiological levels [253-255]. Diboronate 165 is capable of chiral recognition of monosaccharides and gave the best chiral recognition for fructose when tested with a series of different saccharides [255]. 

Both steric and electronic factors are used for chiral recognition of saccharides by the R and S forms of S-3. A difference in PET efficiency is created by the asymmetric immobilization of the amine groups relative to the binaphthyl moiety upon 1 1 complexation of saccharides by d- or L-isomers. For instance, D-fructose is recognized by the R form of S-2 with a large fluorescence enhancement. 

Work by Irie et al. on the control of intermolecular chiral l,l -binapthyl fluorescence quenching by chiral amines [66] and the use of 1,1 -binaphthyl in the recognition of chiral amines by Cram [67] were the inspiration behind the design of 26 (R or S). Chiral recognition of saccharides by 26 (R or S)... 

Cyclodextrins exhibit chiral recognition characteristics, because the cavities inside are formed from optically active sugars. Cyclodextrins have been introduced as ligands in NPLC as early as 1989 for the separation of sugar alcohols and various saccharides [35]. Risley and Strege [36] used such a stationary phase for the separation of polar chiral compounds, which could not be resolved under nonaqueous NP conditions. 

In this chapter, the development and chiral recognition mechanism of poly-saccharide-based CSPs for the efficient chromatographic separation of enantiomers have been outlined. The recognition abilities of native polysaccharides are not sufficient for use as CSPs, but their abilities can be substantially improved by the proper modifications of their structures. At present, more than 10 kinds of polysaccharide-based CSPs are commercially available and practically used around the world as... 

In designing siderophore mimics, solubility and molecular recognition are key issues. A saccharide can provide a chiral... 

Chiral guanidinium-based ligands have also been used for recognition of diastereomeric salts of saccharides [45]. Some promising ligands with guani-dinium structure have not been studied yet [46], and some of them have been used as catalysts for the nitroaldol reaction [47] and Michael addition to a,P-unsaturated ketones [48]. 

As saccharides, CyDs are chiral and exhibit dtiral recognition, that is they form dia-stereomeric complexes, usually of different stability, with enantiomeric spedes. 

---