Amphiphilic Anthracene-Amino Acid Conjugates as Simple Carbohydrate Receptors in Water

N -Alkylation of amino acid methyl esters with 9,10-bis-chloromethylanthracene, followed by methyl ester hydrolysis, yielded water-soluble amphiphilic amino acid-anthracene conjugates. In NMR-titration experiments, a l -arginine-anthracene conjugate was demonstrated to recognize p -nitrophenyl glycosides and sialylated oligosaccharides in D 2 O in a manner sensitive to the carbohydrate structure.

Keywords:

• N -alkylation
• Glycoconjugate
• Nmr
• Hybrid