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Reference type: Journal
Authors: Herm M, Schrader T
Article Title: Towards synthetic adrenaline receptors.
Publication date: 2000
Journal: Chemistry - A European Journal
Volume: 6
Issue: (1)
Page numbers: 47-53.
DOI: 10.1002/(SICI)1521-3765(20000103)6:1<47::AID-CHEM47>3.0.CO;2-I

Abstract: 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


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