Abstract
A detailed analysis is presented of the nuclear ( 1H and 13C) magnetic resonance (n.m.r.) properties of sucrose, using both D 2O and dimethyl sulfoxide- d 6 as solvents, based on measurements of coupling constants, chemical shifts, T 1 relaxation times, and nuclear Overhauser enhancements. Molecular modelling (HSEA calculations) suggests a strong conformational preference about the glycosidic linkages that is near to that for sucrose in the crystalline state, and this conformational rigidity is fully supported by the n.m.r. data, in terms of lack of influence of changes in concentration and temperature on the relevant n.m.r. parameters. The restricted rotation for the 1-hydroxymethyl group of the fructose residue is related to the persistence of the intramolecular hydrogen-bond between O-1 f and O-2 g. The presence of this bond was established for solutions in (CD 3) 2SO by the observation of isotopic chemicashifts on partial deuteration of the hydroxyl groups. The orientation of the 6-hydroxyl methyl group of the fructose residue is not that present in the crystalline state but, in (CD 3) 2SO, it may be intramolecularly hydrogen-bonded, as was demonstrated by titration of the hydroxyl groups with CD 3OD. Observations are made regarding hydrophobic topographies common to sucrose, saccharin, and 1-chloro-1-deoxysucrose, which may have a bearing on sweetness.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
