EFFECT OF STEREOCHEMISTRY ON HYDROXYL PROTON CHEMICAL-SHIFTS AND COUPLING-CONSTANTS IN CARBOHYDRATES

Chemical shifts and coupling constants of hydroxyl protons for a series of simple carbohydrates are reported and several trends extracted: (1) chemical shifts are relatively independent of the experimental conditions if referenced to water; (2) chemical shifts are sensitive to the orientation of the HO group and its neighbors; and (3) coupling constants fall within a relatively narrow range, which is indicative of rotational averaging. These observations suggest that NMR parameters of hydroxyl protons can provide important diagnostic information about the stereochemistry of simple carbohydrates and may prove useful for analysis of more complex compounds.