Neutron diffraction of alpha, beta and gamma cyclodextrins: hydrogen bonding patterns

Journal of Biomolecular Structure & Dynamics
B HingertyW Saenger

Abstract

Cyclodextrins (CD's) have proved useful as model systems for the study of hydrogen bonding. They are torus-shaped molecules composed of six(alpha), seven(beta) or eight(gamma) (1----4) linked glucoses. Because of their particular geometry, they are able to act as a "host" to form inclusion complexes with "guest" molecules very much like enzymes. Cyclodextrins have been shown to exert catalytic activity on suitable included-substrate molecules; they catalyze the hydrolysis of phenylacetates, of organic pyrophosphates and of penicillin derivatives. They also accelerate aromatic chlorinations and diazo coupling by means of their primary and/or secondary hydroxyl groups, so that the rates of hydrolysis are enhanced by up to a factor of 400. In order to understand the hydrogen bonding in these enzyme models, neutron diffraction data were collected to unambiguously determine the hydrogen atom positions, which could not be done from the x-ray diffraction data. alpha-CD has been shown to have two different structures with well-defined hydrogen bonds, one "tense" and the other "relaxed". An "induced-fit"-like mechanism for alpha-CD complex formation has been proposed. Circular hydrogen bond networks have also been found for alpha-CD due...Continue Reading

References

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Citations

Jan 1, 1987·European Biophysics Journal : EBJ·J E KoehlerW F van Gunsteren
Dec 14, 2006·Chemistry : a European Journal·Axel Müller, Gerhard Wenz
Jun 20, 2017·Current Protocols in Nucleic Acid Chemistry·Geeta MeherRadhakrishnan P Iyer
Jul 1, 1986·International Journal of Peptide and Protein Research·I L Karle
Sep 17, 2019·Biochimica Et Biophysica Acta. General Subjects·Helena Ø RasmussenJan Skov Pedersen

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