Trehalose optical rotation

Thomsen,133 Smolenski and Kozlowski,134 and Reeves and Blouin131 observed that sodium hydroxide has a relatively large effect on the optical rotation of sucrose. a,a-TrehaloSe,m on the other hand, is affected only slightly. Thomsen133 and Reeves and Blouin131 made no attempt to interpret the unusual behavior of sucrose Smolenski and Kozlowski,134 however, assumed that the reaction was that of alcoholate formation, and they calculated dissociation constants for sucrose. 

Three distinctly different optical rotations have been recorded for the three D-glucosidic linkages of the trehaloses (see Tables II, III, IV, V, VII, and VIII). Stan k has compared experimental values of optical rotations with those calculated by Hudson s and Klyne s rules (see Section V). 

An alteration in the optical rotation of a, a-trehalose has been observed in alkaline solution. This was attributed to movement of axial hydroxyl groups into equatorial positions. 

Analysis of the enzymically synthesized product by chemical and enzymic methods, as well as by optical rotation, showed that it was identical with the trehalose phosphate isolated from the fermentation products of dry yeast. ... 

A newly developed calculation model for optical rotation has been applied to the determination of the conformation in solution of jS-lactose and trehalose. ... 

This can be analysed by optical rotation, with some rather interesting results. The sugars that were studied a few years ago were OL -methyl-maltoside, cellobiose and trehalose. They have one factor in common, they are composed of two glucose units, but with different linkages, maltose a-1-4, cellobiose B- 1-4, and trehalose 01-1-1. There are thus different conformations of this molecule, which consists of the same two sugar units. 

The Isorotation Rules of Hudson are applicable to disaccharides. As shown in Table I, all a-D-glucopyranosyl-D-glucoses show high dextro optical rotations, whereas ) -D-glucopyranosyl-D-glucoses have far smaller rotations. Likewise, consideration of the optical rotatory relationships of three isomers indicates that both anomeric carbons of naturally-occurring trehalose... 

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