Expanding sapphyrin: towards selective phosphate binding.
The anion-templated syntheses and binding properties of novel macrocyclic oligopyrrole receptors in which pyrrole rings are linked through amide or imine bonds are described. The efficient synthesis was accomplished by anion-templated [1+1] Schiff-base condensation and acylation macrocyclization reactions. Free receptors and their host-guest complexes with hydrochloric acid, acetic acid, tetrabutylammonium chloride, and hydrogen sulfate were analyzed by single-crystal X-ray diffraction analysis. Stability constants with different tetrabutylammonium salts of inorganic acids were determined by standard 1H NMR and UV/Vis titration techniques in [D6]DMSO/0.5% water solution. According to the titration data, receptors containing three pyrrole rings (10 and 12) exhibit high affinity (log Ka=5-7) for bifluoride, acetate, and dihydrogen phosphate, and interact weakly with chloride and hydrogen sulfate. The amido-bipyrrole receptors 11 and 13 with four pyrrole rings exhibit 10(4)- and 10(2)-fold selectivity for dihydrogen phosphate, respectively, as inferred from competitive titrations in the presence of tetrabutylammonium acetate.
Katayev
Evgeny A
EA
Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St., 28, Moscow, 119991 (Russia), Fax: (+7) 499-135-5085.|Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1/3, Moscow, 119991 (Russia).
Boev
Nikolay V
NV
Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1/3, Moscow, 119991 (Russia).
Myshkovskaya
Ekaterina
E
Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St., 28, Moscow, 119991 (Russia), Fax: (+7) 499-135-5085.
Khrustalev
Victor N
VN
Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St., 28, Moscow, 119991 (Russia), Fax: (+7) 499-135-5085.
Ustynyuk
Yu A
YA
Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1/3, Moscow, 119991 (Russia).|Research Center for Magnetic Tomography and Spectroscopy, M. V. Lomonosov Moscow State University, Leninskie Gory, 1, Bldg 73, Moscow, 119991 (Russia).
D000838:Anions / Q000737:chemistry; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
D000838:Anions; D010710:Phosphates; D011166:Porphyrins; C440448:sapphyrin
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