Enzymic degradation of starch generally results in the production of glucose, maltose, maltotriose, etc., Le. a long series of linear or branched chain malto-oligomers, known as dextrins.Dextrins are heterogeneous, amorphous, hygroscopic substances, produced in large quantities for the food, textile, paper and other industries. They are also consumed without prior isolation in such products as e.g. beer and bread. This type of starch degradation is a true hydrolytic process, as the primary product from the splitting of the glycosidic linkage reacts with one molecule of water.If however, the starch is degraded by the glucosyltransferase enzyme (CGT), the primary product of the chain splitting undergoes an intramolecular reaction without the participation of a water molecule. The ex-1,4-linked cyclic products are formed; they are known as cyclodextrins (Figure 1-1). a-AMYLASE ~ .. ~ C> C> c:> J. Szejtli, Cyclodextrin Technology © Springer Science+Business Media Dordrecht 1988 CYCLODEXTRIN TECHNOLOGY APOLAR CAVITY SECONDARY HYDROXYLS ~PRIMARY HYDROXYLS Fig .1-6. Functional structural scheme of cyc1odextrins.making it a rigid structure. This is the probable explanation for the observation that ~-cyclodextrin has the lowest solubility of all the cyclodex trins. The hydrogen-bond belt is incomplete in the a-cyclodextrin molecule, as one glucopyranose unit is in a distorted position [ 301,304 J. As a consequence only four of the six possible H-bonds can be established. The y-cyclodextrin is a non-coplanar, more flexible structure, and is therefore the more soluble of the three. Equilibrium constants for the hydrogendeuterium exchange in the secondary hydroxyls (0.65 for 6-cyclodextrin, 0.75 for a-cyclodextrin and 0.85 for amylose) indicate the strongest H-bond system to be in ~-cyclodextrin [ 51 J.According to conformation-energy maps [ 325 J, hydrogen bonding between the C2 and C3 hydroxyls results in a lowering of energy by 20 kcal/mole (83.7 kJ/mole) in a-cyclodextrin, and of 30 kcal/mole (125 kJ/mole) in ~-cyclodextrin. J'2 J 23 J 34 J 45 J 56 .. J 561> J s .. , 0$1>