Towards synthetic adrenaline receptors.
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.
Herm
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Institut für Organische Chemie und Makromolekulare Chemie II, Heinrich-Heine-Universität Düsseldorf, Germany.
Schrader
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D000605:Amino Alcohols / Q000138:chemical synthesis*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004164:Diphosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D015394:Molecular Structure; D011941:Receptors, Adrenergic / Q000737:chemistry* / Q000378:metabolism; D013379:Substrate Specificity; D014992:Xylenes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism
D000605:Amino Alcohols; D004164:Diphosphonates; D004988:Ethers, Cyclic; D011941:Receptors, Adrenergic; D014992:Xylenes; D004121:Dimethyl Sulfoxide