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Titolo:
Molecular recognition studies on supramolecular systems. 29. Anilino- and m-toluidino-beta-cyclodextrins: Structural and conformational analyses and molecular recognition of aliphatic alcohols
Autore:
Liu, Y; You, CC; Kunieda, M; Nakamura, A; Wada, T; Inoue, Y;
Indirizzi:
Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China Nankai Univ Tianjin Peoples R China 300071 anjin 300071, Peoples R China JST, ERATO, Inoue Photochirogenesis Project, Toyonaka, Osaka 5650085, Japan JST Toyonaka Osaka Japan 5650085 Project, Toyonaka, Osaka 5650085, Japan Osaka Univ, Fac Engn, Dept Mol Chem, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 ol Chem, Suita, Osaka 5650871, Japan
Titolo Testata:
SUPRAMOLECULAR CHEMISTRY
fascicolo: 3, volume: 12, anno: 2000,
pagine: 299 - 316
SICI:
1061-0278(2000)12:3<299:MRSOSS>2.0.ZU;2-V
Fonte:
ISI
Lingua:
ENG
Soggetto:
INDUCED CIRCULAR-DICHROISM; COLOR-CHANGE INDICATOR; CHARGE-TRANSFER FLUORESCENCE; INCLUSION COMPLEXATION; AMINO-ACIDS; AQUEOUS-SOLUTION; ENANTIOSELECTIVE RECOGNITION; NAPHTHALENE DERIVATIVES; ALPHA-CYCLODEXTRIN; CHIRAL RECOGNITION;
Keywords:
modified cyclodextrins; 2D-NMR analyses; inclusion complexation; molecular recognition; aliphatic alcohol;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
54
Recensione:
Indirizzi per estratti:
Indirizzo: Liu, Y Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China Nankai Univ Tianjin Peoples R China 300071 00071, Peoples R China
Citazione:
Y. Liu et al., "Molecular recognition studies on supramolecular systems. 29. Anilino- and m-toluidino-beta-cyclodextrins: Structural and conformational analyses and molecular recognition of aliphatic alcohols", SUPRAMOL CH, 12(3), 2000, pp. 299-316

Abstract

Mono (6-anilino-6-deoxy)-beta -cyclodextrin (1) and mono[6-(m-toluidino)-6-deoxy]-beta -cyclodextrin (2) were synthesized and characterized. Circulardichroism and fluorescence spectral studies and fluorescence lifetime measurements have been performed to elucidate the conformations of 1 and 2 in aqueous buffer solution. 1-D and 2-D NMR spectra of 2 have been measured in D2O to deduce its structure and detailed conformation in solution. From thecircular dichroism, fluorescence, and NMR spectroscopic studies, it was revealed that the substituents appended to 1 and 2 penetrate into the cyclodextrin cavity forming a stable self-inclusion complex in aqueous solution, and also that the short linkage between the m-toluidino and cyclodextrin moieties makes the cyclodextrin ring of 2 deformed to some extent. The complexstability constants (K-S) of 1 and 2 for a series of aliphatic alcohols have been determined by using spectropolarimetric titrations in aqueous phosphate buffer solution (pH 7.20) at 25 degreesC to elucidate the role of introduced substituents and the weak interactions involved in inclusion complexation by the modified cyclodextrins. The results obtained indicate that thevan der Waals and hydrophobic interactions mainly contribute to the formation of complexes between the cyclodextrins and aliphatic alcohols, and the inclusion complexation process involves the induced-fit mechanism. Modifiedbeta -cyclodextrin 2 can recognize not only the size, shape, and hydrophobicity of the guest molecules, but also chiral guests, affording a moderate enantioselectivity of 1.55 for (+)/(-)-borneol.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 07:52:14