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Titolo:
Enantioselective recognition of aliphatic amino acids by organoselenium modified beta-cyclodextrins
Autore:
Liu, Y; Li, B; 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 Osakasakav, Dept Mol Chem, ERATO, Inoue Photochirogenesis Project, Suita, O Osaka Univ Suita Osaka Japan 565 noue Photochirogenesis Project, Suita, O
Titolo Testata:
SUPRAMOLECULAR CHEMISTRY
fascicolo: 3, volume: 10, anno: 1999,
pagine: 173 - 184
SICI:
1061-0278(1999)10:3<173:EROAAA>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
MOLECULAR RECOGNITION; ALPHA-CYCLODEXTRIN; INCLUSION COMPLEXATION; ARTIFICIAL ENZYMES; CHEMISTRY; BINDING;
Keywords:
enantioselective recognition; modified cyclodextrin; amino acids; organoselenium; inclusion complexation;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
34
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., "Enantioselective recognition of aliphatic amino acids by organoselenium modified beta-cyclodextrins", SUPRAMOL CH, 10(3), 1999, pp. 173-184

Abstract

A series of novel organoselenium modified beta-cyclodextrins (CDs) bearingan aromatic group 1-7 have been synthesized by a convenient method in satisfactory yields. Spectrophotometric titrations have been performed in aqueous buffer solution (pH 7.20) at 25.0 degrees C to give the complex stability constants (K-s) and Gibbs free energy change (-Delta G degrees) for the 1:1 inclusion complexation of the six organoselenium modified beta-cyclodextrins with some selected aliphatic amino acids. Inclusion complexation of mono-[6-(naphthylseleno-6-deoxy]-beta-cyclodextrin 7 with aliphatic amino acids was too weak to be observed, which is attributable to the stronger self-inclusion of naphthylseleno moiety attached to the primary side of cyclodextrin into the cavity. However, the other modified beta-cyclodextrins carrying one arylseleno moiety as a probe for differential UV spectrometry were found to recognize not only the size and shape but also the chirality of amino acids. Among arylseleno CDs 1-6, 3 showed the highest enantioselectivityof 27 for L-Ala over the antipodal D-Ala. The molecular recognition ability and enantioselectivity for amino acids of these seven modified beta-cyclodextrins are discussed from the viewpoints of the size/shape-fit concept, substituent effect and the multipoint recognition mechanism. The inclusion complexation of these modified beta-cyclodextrins with LID-amino acids may be more explicitly understood in terms of the complementary geometrical relationship and the induced-fit interaction between the host and the guest.

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Documento generato il 13/07/20 alle ore 06:24:47