Shallenberger, R.S., Acree, T.E. and Mclellan, M.R. 1985.
Relation between structure and optical rotation in the sugar group.
190th American Chemical Society National Meeting, Chicago, Ill., Usa, Sept 190(0):
A procedure has been developed that affords calculation, from the molecular rotation, of sugar conformation in water solution and includes the stereoposition of extracyclic groups. Conversely, approximation of a solution structure affords calculation of the corresponding molecular rotation, to be compared with the observed molecular rotation. The procedure is based upon calculation of the helical angle described by ring substituent hydroxyl groups (oxygen atoms) to yield [M]oh from a simple algebraic expression. Those values, plus the superposed contribution of individual asymmetric carbon atoms, [M]c, yields [M]D calculated. Agreement with the observed molecular rotation is excellent. Application of the procedure to free aldo- and ketopyranoses, 6-deoxy-pryanoses, 1,6-anhydro-B-D-pryanoses and methyl-furanosides will be presented.