Structure and solution equilibria of D-glucose and D-mannose sulfite adducts.
An X-ray crystallographic study has confirmed that the potassium bisulfite adducts of D-glucose and D-mannose have open-chain structures with R and S configurations respectively at C-1. NMR studies have shown that each sugar gives rise to two bisulfite compounds, and solution-state structures and conformations of these isomers have been deduced from analysis of (1)H NMR spectra. (13)C NMR data for the four adducts are given. Furanose forms of the D-glucose and D-mannose have been detected in the equilibrium solutions.
Cole
E R
ER
School of Chemistry, University of New South Wales, Sydney 2052, Australia.
Craig
D C
DC
Fitzpatrick
L J
LJ
Hibbert
D B
DB
Stevens
J D
JD
D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D005947:Glucose / Q000737:chemistry* / Q000378:metabolism; D007536:Isomerism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D012996:Solutions / Q000737:chemistry; D013447:Sulfites / Q000737:chemistry* / Q000378:metabolism
D012996:Solutions; D013447:Sulfites; D005947:Glucose; D008358:Mannose