Study of carbohydrate structure and reactivity by modern NMR methods and isotopic labeling
Chemical methods are described for preparing unenriched and (1-/sup 13/C)-enriched 5-deoxy- and 5-O-methylpentoses in the D or L configuration. The /sup 1/H and /sup 13/C NMR spectra of these compounds have been interpreted and the carbon spectra assigned with the aid of 2D /sup 13/C-/sup 1/H chemical-shift correlation spectroscopy. The tautomeric composition in /sup 2/H/sub 2/O has been quantitated with the aid of (1-/sup 13/C)-enriched derivatives. The branched-chain pentose, DL-apiose has been synthesized in good yield by a new and simple chemical method that can be adapted to prepare (1-/sup 13/C)-, (2-/sup 13/C)-, (1-/sup 2/H)- and/or (2-/sup 2/H)-enriched derivatives. The solution composition of D-idose in D/sup 2/O has been examined by /sup 13/C NMR spectroscopy using (/sup 13/C)-enriched compounds. In addition to two furanoses and two pyranoses, aldehyde and hydrate forms have been detected and quantified. The solution composition of D-talose has been investigated by /sup 13/C NMR spectroscopy using (1-/sup 13/C)talose. The tautomeric composition has been determined at 28/sup 0/, and the results show equivalent amounts of the acyclic aldehyde and hydrate. Several structurally modified furanose sugars were synthesized to assess the extent the Thorpe-Ingold effect promotes rings formation and enhances rates of ring-closure.
- Research Organization:
- Notre Dame Univ., IN (USA)
- OSTI ID:
- 7003936
- Country of Publication:
- United States
- Language:
- English
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62 RADIOLOGY AND NUCLEAR MEDICINE
BIOSYNTHESIS
CARBOHYDRATES
CARBON 13
CARBON ISOTOPES
CHEMICAL PREPARATION
DEUTERIUM COMPOUNDS
EVEN-ODD NUCLEI
HEAVY WATER
HYDROGEN COMPOUNDS
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MAGNETIC RESONANCE
MONOSACCHARIDES
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
PENTOSES
RESONANCE
SACCHARIDES
SPECTRA
STABLE ISOTOPES
SYNTHESIS
WATER