High resolution 1H NMR structural studies of sucrose octaacetate in supercritical carbon dioxide.
High pressure (HP), high resolution (HR), proton nuclear magnetic resonance (1H NMR) spectroscopy has been utilized for the first time to investigate the solution structure of a carbohydrate based system, sucrose octaacetate (SOA), in supercritical CO2. The studies indicate that the average solution state conformation of the alpha-D-Glucopyranosyl ring of SOA in scCO2 medium is consistent with the 4C1 chair form, while the beta-D-fructofuranosyl ring adopts an envelope conformation. The investigations also suggest that scCO2 is a promising medium to study the solution structure and conformation of acetylated sugar systems. Spectral manifestations of a specific interaction between the acetate methyl protons and CO2 molecules are also presented.
Chandrika
Baby
B
Department of Chemistry, Kenan and Venable Laboratories, University of North Carolina, Chapel Hill, 27599-3290, USA.
Schnackenberg
Laura K
LK
Raveendran
Poovathinthodiyil
P
Wallen
Scott L
SL
D000107:Acetylation; D002245:Carbon Dioxide; D025924:Chromatography, Supercritical Fluid; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents; D013395:Sucrose / Q000031:analogs & derivatives* / Q000737:chemistry
D012997:Solvents; C026879:sucrose octaacetate; D002245:Carbon Dioxide; D013395:Sucrose