Cholic acid-based fluorescent probes for enantioselective recognition of trifunctional amino acids.
The ditopic fluorescent photoinduced electron transfer (PET) amino acid sensory probes and were designed and synthesized from cholic acid. To confer the probes with specific binding ability, an amidothiourea moiety and a cyclic diamino-chiral receptive site were introduced on the C17 side chain and the C7 and C12 hydroxyl pendants, respectively. In acetonitrile, the probes demonstrated differential binding toward trifunctional amino acids like serine, lysine, threonine and tyrosine against other simple amino acids. Enantioselectivities (KD/KL) of up to 8.9 and sensitivities in the micromolar range with the probes were observed for trifunctional amino acids.
Wang
Hao
H
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR, China.
Chan
Wing-Hong
WH
Lee
Albert W M
AW
D000596:Amino Acids / Q000737:chemistry*; D001665:Binding Sites; D019826:Cholic Acid / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D000596:Amino Acids; D005456:Fluorescent Dyes; D019826:Cholic Acid