Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin(426 views) Di Blasio B, Galdiero S, Saviano M, Pedone C, Benedetti E, Rizzarelli E, Pedotti S, Vecchio G, Gibbons WA
Keywords: Crystal Structure, Cyclodextrins, Cyclomaltoheptaose, Difunctionalized β-Cyclodextrin, Beta Cyclodextrin Derivative, Article, Crystallography, Drug Structure, Drug Synthesis, Priority Journal, Reaction Analysis, Stereochemistry, Beta-Cyclodextrins, Carbohydrate Sequence, Magnetic Resonance Spectroscopy, Models, Molecular, Molecular Sequence Data, Optical Rotation, Spectrometry, Fast Atom Bombardment, X-Ray Diffraction, Difunctionalized-Cyclodextrin,
Affiliations: Dipartimento di Chimica, Università della Basilicata, Via N.Sauro 85, I-85100 Potenza, Italy
Biocrystallography Research Centre, Dipartimento di Chimica, Unirersita Federico II di Napoli, via Mezzocannone 4, I-80134 Naples, Italy
Dipartimento di Scienze Chimiche, Università di Catania, V. le A. Doria 8, I-95125 Catania, Italy
Inst. Stud. Sostanze Naturali I., CNR, V. le A. Doria 8, I-95125 Catania, Italy
Pharmaceutical Chemistry Department, University of London, 29 / 39, Brunswick Sq., London WCIN IAX, United Kingdom
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Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin
6 (I), 6 (II) -Diamino-6 (I), 6 (II) -dideoxy-cyclomaltoheptaose was prepared using the regioselective procedure described by Tabushi. The difunctionalized beta-cyclodextrin crystallizes as hextadecahydrate in the orthorhombic space group P2 (1) 2 (1) 2 (1), with a = 11. 395 (3), b = 32. 989 (9), c = 17. 560 (5) Angstrom, V = 6601 Angstrom (3), Z = 4, The structure was solved by molecular replacement techniques using the program PATSEE and was refined to a conventional final R = 0. 058 for the 5031 observed reflections with 1 greater than or equal to 3 sigma (I). The beta-CD macrocycle presents only slight differences with respect to uncomplexed hydrated or methylated beta-CD. The macrocycle structure maintains an approximate seven-fold symmetry. The round shape of the cyclodextrin ring is stabilized by intramolecular O-H. O H-bonds between the secondary hydroxyl groups of neighbouring glucose residues. Along the a axis, the beta-CD molecules are arranged in columns; the macrocycles form a herring-bone pattern, so that the cavity of each beta-CD molecule is closed at each end by neighbouring molecules. The macrocycles are directly linked to each other by H-bonds involving either primary and secondary hydroxyl or amino groups of symmetry-related molecules. The resulting layers are connected to each other by a dense intermolecular hydrogen-bond network, in which solvent molecules participate
Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin