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Strain-induced 'band flips' in cyclodecaamylose and higher homologues


Jacob, J and Gessler, K and Hoffmann, D and Sanbe, H and Koizumi, K and Smith, SM and Takaha, T and Saenger, W, Strain-induced 'band flips' in cyclodecaamylose and higher homologues, Angewandte Chemie International Edition, 37, (5) pp. 606-609. ISSN 1433-7851 (1998) [Refereed Article]

Copyright Statement

Copyright 1998 WILEY-VCH Verlag GmbH

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DOI: doi:10.1002/(SICI)1521-3773(19980316)37:5<605::AID-ANIE605>3.0.CO;2-C


In the well–known cyclodextrins, all glucose units are cis-oriented and connected by O3···O2´ hydrogen bonds forming cyclically closed bands. In larger cyclodextrins (cycloamyloses) with 10 and more glucoses, strain induced in the macrocycle is relieved by two 180º flips to trans orientation between diametrically opposed glucose units. These two "band flips" are stabilized by hydrogen bonds (O3···O5´ and O3···O6´), and lead to butterflylike structures. In the figures, cyclodextrins with 7 and 14 glucoses are shown; atoms O2, O3 are red, O6 blue, C6 grey, arrows mark chain direction, and dashed lines indicate hydrogen bonds.

Item Details

Item Type:Refereed Article
Keywords:glucose, cycloamylose, alpha-1-4-glucose
Research Division:Biological Sciences
Research Group:Plant biology
Research Field:Plant physiology
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the biological sciences
UTAS Author:Smith, SM (Professor Steven Smith)
ID Code:101576
Year Published:1998
Web of Science® Times Cited:69
Deposited By:Plant Science
Deposited On:2015-06-26
Last Modified:2015-09-21

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