Taylor & Francis Group
Browse
gsch_a_1692138_sm3836.docx (10.43 MB)

Distinguishing amines with an amino acid appended resorcinarene-based cavitand

Download (10.43 MB)
journal contribution
posted on 2019-11-18, 11:46 authored by Tayyebeh Panahi, Holly L. Anderson, Karla I. Castro, John D. Lamb, Roger G. Harrison

Resorcinarene-based deep cavitands including glutamic acid methyl resorcinarene (GMA) and glutamic acid undecyl resorcinarene (GUA) have been synthesised and their amine binding properties analysed. The cavitands are designed with hydrogen bonding groups on their upper rim (glutamic acids) and hydrophobic groups, on their lower rims. Along with the aromatic groups of the resorcinarene, these cavitands have many sites for guest binding. The cavitands form kite-like structures in dimethylsulfoxide, acetone, and water. The binding of GMA with amines, including guanidine containing drug compounds, was studied in DMSO by UV-vis titration and compared to that of phthalyl glutamic acid. The obtained binding constants for GMA to amines (K values) were in the range of 12–136 × 103 M−1 for benzyl amines and 4.3–153 × 103 M−1 for guanidine compounds. GMA shows a binding preference for more basic and less sterically encumbered amines and slightly stronger binding to S-enantiomers.

History

Usage metrics

    Supramolecular Chemistry

    Licence

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC