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Optical Rotation of the Isomeric Trehaloses

Abstract

MOLECULAR rotation of any glycoside containing an optically active aglycone is equal, according to Klyne1, to the sum of the molecular rotations of the corresponding methylglycoside and aglycone. This rule has been used successfully many times for the calculation of molecular rotations of the glycosides containing steroid substances as aglycones2, later for the calculation of molecular rotations of glycoalkaloids3. Hitherto, this rule has not been used for calculations of molecular rotations of disaccharides, which can also be considered as glycosides. Some complications are to be expected, as a disaccharide, containing two hexosepyranoid units, can exist in at least eleven isomers which differ in their values of specific and molecular rotations. The contribution of the aglyconic part of the molecule will influence the molecular rotation of the whole molecule in an unknown fashion.

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STANĚK, J. Optical Rotation of the Isomeric Trehaloses. Nature 179, 97–98 (1957). https://doi.org/10.1038/179097a0

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