Cholic acid-based fluorescent probes for enantioselective recognition of trifunctional amino acids

Hao Wang, Wing Hong CHAN*, Albert W M LEE

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

The ditopic fluorescent photoinduced electron transfer (PET) amino acid sensory probes 1a and 1c 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.

Original languageEnglish
Pages (from-to)929-934
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume6
Issue number5
DOIs
Publication statusPublished - 2008

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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