Stable isotopically-enriched ribonucleosides: synthesis and use in studies of furnose, N-glycoside and hydroxymethyl group conformation
(1'-/sup 13/C)- and (2'-/sup 13/C)-enriched ribonucleosides (adenosine, cytidine, uridine) (99 atom-% /sup 13/C) have been synthesized in millimole quantities. /sup 1/H (300 MHz) and /sup 13/C (75 MHz) NMR spectra have been obtained from which /sup 13/C-/sup 1/H and /sup 13/C-/sup 13/C spin couplings have been measured and studied in terms of preferred furanose and N-glycoside conformation. Using a recently-reported chemical method to stereoselectively deuterate hydroxymethyl groups of sugars adenosine, cytidine and uridine were synthesized with chiral C5' hydroxymethyl groups, permitting unequivocal stereochemical assignment of the NMR signals of these protons. From these assignments the conformational properties of the exocyclic groups were assessed based on /sup 1/H-/sup 1/H spin coupling. A theoretical (computational) analysis of the use of /sup 1/H-/sup 1/H internuclear distances to assess N-glycoside conformation in purine and pyrimidine nucleosides was conducted. DESERT (Deuterium Substitution Effects on Proton Relaxation Times) experiments using (1'-/sup 2/H)2,2'-anhydrouridine and uridine have been conducted to test the validity of these theoretical considerations.
- Research Organization:
- Univ. of Notre Dame, IN
- OSTI ID:
- 5334415
- Report Number(s):
- CONF-8606151-
- Journal Information:
- Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Journal Name: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States) Vol. 45:6; ISSN FEPRA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
ADENOSINE
AZINES
BARYONS
BIOSYNTHESIS
CARBON 13
CARBON ISOTOPES
CYTIDINE
DEUTERIUM
ELEMENTARY PARTICLES
EVEN-ODD NUCLEI
FERMIONS
HADRONS
HETEROCYCLIC COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEONS
NUCLEOSIDES
NUCLEOTIDES
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PROTONS
PYRIMIDINES
RESONANCE
RIBOSIDES
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
SYNTHESIS
TRACER TECHNIQUES
URACILS
URIDINE