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Towards Synthetic Adrenaline Receptors
Author(s) -
Herm Michael,
Schrader Thomas
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000103)6:1<47::aid-chem47>3.0.co;2-i
Subject(s) - solvophobic , chemistry , molecule , aqueous solution , amphiphile , micelle , stereochemistry , methanol , organic chemistry , polymer , copolymer
The macrocyclic bisphosphonate 2 forms complexes with amino alcohols, amines, and amino acid esters with high association constants in polar organic solvents. Exertion of solvophobic interactions inside the macrocyclic cavity in DMSO and methanol leads to specificity for guest molecules with hydrophobic moieties. Experimental evidence is presented for the insertion of the guest molecules' nonpolar groups into the macrocycle's hydrophobic cavity. NMR spectra of complexes with 2 in DMSO show a molecular imprint of the guest molecule; this gives information about its location inside the macrocycle. In aqueous solutions strong self‐association of 2 occurs, which is explained by distinct structural similarities between 2 and micelle‐forming phospholipids.