Cyclodextrins
Title: Cyclodextrins
Additional Names: Cycloamyloses; cycloglucans; Schardinger dextrins
Literature References: Naturally occurring clathrates, q.v. Obtained from the action of Bacillus macerans amylase on starch to form homogeneous cyclic a-(1®4) linked D-glucopyranose units. a-, b- and g-cyclodextrins are composed of six, seven and eight units, resp. Isoln of b-cyclodextrin: A. Villiers, Compt. Rend. 112, 536 (1891); of a- and b-cyclodextrin: F. Schardinger, Z. Untersuch. Nahr. Genussm. 6, 865 (1903); of g-cyclodextrin: K. Freudenberg, R. Jacobi, Ann. 518, 102 (1935). X-ray mol wt determn: D. French, R. E. Rundle, J. Am. Chem. Soc. 64, 1651 (1942); D. French et al., ibid. 72, 5150 (1950). Have hydrophobic cavities; form inclusion compds with organic substances, salts and halogens in the solid state or in aq solns. Model for enzyme action: I. Tabushi, Acc. Chem. Res. 15, 66 (1982). Reviews: D. French, Adv. Carbohydr. Chem. 12, 189-260 (1957); J. A. Thoma, L. Stewart, Starch: Chemistry and Technology vol. 1, R. L. Whistler, E. F. Paschall, Eds. (Academic Press, New York, 1965) pp 209-249; F. Cramer, H. Hettler, Naturwissenschaften 154, 625-632 (1967). Book: M. L. Bender, M. Komiyama, Cyclodextrin Chemistry (Springer-Verlag, New York, 1978) 96 pp.
 
Derivative Type: a-Cyclodextrin
Additional Names: Cyclohexaamylose
Molecular Formula: C36H60O30
Molecular Weight: 972.84
Percent Composition: C 44.45%, H 6.22%, O 49.34%
Properties: Hexagonal plates or blade-shaped needles. [a]D +150.5°.
Optical Rotation: [a]D +150.5°
 
Derivative Type: b-Cyclodextrin
Additional Names: Cycloheptaamylose
Molecular Formula: C42H70O35
Molecular Weight: 1134.98
Percent Composition: C 44.45%, H 6.22%, O 49.34%
Properties: Parallelogram shaped crystals. [a]D +162.0°.
Optical Rotation: [a]D +162.0°
 
Derivative Type: g-Cyclodextrin
Additional Names: Cyclooctaamylose
Molecular Formula: C48H80O40
Molecular Weight: 1297.12
Percent Composition: C 44.45%, H 6.22%, O 49.34%
Properties: Square plates or rectangular rods. [a]D +177.4°.
Optical Rotation: [a]D +177.4°
 
Use: As complexing agent; in study of enzyme action.

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