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Titolo:
Difunctionalized beta-cyclodextrins: synthesis and X-ray diffraction structure of 6(I),6(II)-dideoxy-6(I),6(II)-bis[2-(2-pyridyl)ethylamino]-beta-cyclomaltoheptaose
Autore:
Saviano, M; Benedetti, E; di Blasio, B; Gavuzzo, E; Fierro, O; Pedone, C; Iacovino, R; Rizzarelli, E; Vecchio, G;
Indirizzi:
CNR, Biocrystallog Res Ctr, I-80134 Naples, Italy CNR Naples Italy I-80134 R, Biocrystallog Res Ctr, I-80134 Naples, Italy Univ Naples 2, Dipartimento Sci Ambientali, I-80010 Caserta, Italy Univ Naples 2 Caserta Italy I-80010 i Ambientali, I-80010 Caserta, Italy CNR, Ist Strutturist Chim G Giacomello, I-00016 Rome, Italy CNR Rome Italy I-00016 trutturist Chim G Giacomello, I-00016 Rome, Italy CNR, Ist Sci Alimentaz, I-83100 Avellino, Italy CNR Avellino Italy I-83100 R, Ist Sci Alimentaz, I-83100 Avellino, Italy Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy Univ Catania Catania Italy I-95125 ento Sci Chim, I-95125 Catania, Italy CNR, Ist Studio Sostanze Nat Interesse Alimentare & Ch, I-95125 Catania, Italy CNR Catania Italy I-95125 eresse Alimentare & Ch, I-95125 Catania, Italy
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
fascicolo: 6, , anno: 2001,
pagine: 946 - 952
SICI:
1472-779X(2001):6<946:DBSAXD>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
AQUEOUS-SOLUTION; FUNCTIONALIZED CYCLODEXTRINS; MOLECULAR RECOGNITION; COPPER(II) COMPLEXES; INCLUSION COMPLEXES; COORDINATION PROPERTIES; ARTIFICIAL RECEPTORS; NEUTRON-DIFFRACTION; CHIRAL RECOGNITION; AMINO-ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
50
Recensione:
Indirizzi per estratti:
Indirizzo: Saviano, M CNR, Biocrystallog Res Ctr, I-80134 Naples, Italy CNR Naples Italy I-80134 allog Res Ctr, I-80134 Naples, Italy
Citazione:
M. Saviano et al., "Difunctionalized beta-cyclodextrins: synthesis and X-ray diffraction structure of 6(I),6(II)-dideoxy-6(I),6(II)-bis[2-(2-pyridyl)ethylamino]-beta-cyclomaltoheptaose", J CHEM S P2, (6), 2001, pp. 946-952

Abstract

The synthesis, solution NMR investigation and solid-state structural characterization of a new difunctionalized beta -cyclodextrin (beta -CD) are reported. 6(I),6(II)-Dideoxy-6(I),6(II)-bis[2-(2-pyridyl)ethylamino]-beta -cyclomaltoheptaose is synthesized for the first time using a regioselective synthetic procedure. On the basis of an aqueous solution NMR investigation, the intramolecular interaction of the two pyridine rings with the upper rim of the cavity is proposed. 6(I),6(II)-Dideoxy-6(I),6(II)-bis[2-(2-pyridyl)ethylamino]-beta -cyclomaltoheptaose, C56H86N4O33, crystallizes in the monoclinic P2(1) space group with cell dimension a=26.303(5), b=15.670(5), c=8.276(2) Angstrom and beta =103.60(2)degrees, and 5.5 molecules of water for each independent beta -cyclodextrin molecule. The structure refines to R=0.103 for 2270 observed reflections [I greater than or equal to3 sigma (I)] and represents the first example of a complete structural characterization ofa branched difunctionalized beta -cyclodextrin. In the solid state, the macrocycle structure maintains an approximate seven-fold symmetry with only small changes occurring in the cyclic carbohydrate conformation where two consecutive primary hydroxy groups are substituted with bulky moieties. The two aminoethylpyridine groups linked to contiguous glucosidic units show different behaviour, with one group extending away from the cavity of the beta-CD, the other remaining in the proximity of the 'mouth' of the cavity. However, in the crystal the aminoethylpyridine group extending away from the cavity of the beta -CD is deeply inserted into the cavity of the adjacent beta -CD molecule translated along the c axis, giving rise to long rows of beta -CD molecules stabilized by these host-guest interactions. The resulting polymeric arrangement has already been observed in crystal structures of other monosubstituted beta -CDs.

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Documento generato il 11/07/20 alle ore 06:13:13