sup 13 C-enriched ribonucleosides: Synthesis and application of sup 13 C- sup 1 H and sup 13 C- sup 13 C spin-coupling constants to assess furanose and N-glycoside bond conformations

Journal Article · Wed Sep 26 04:00:00 EDT 1990 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00176a043· OSTI ID:5322526

Kline, P C; Serianni, A S ^[1]

---

1. Univ. of Notre Dame, IN (USA)

Adenosine (1), cytidine (2), guanosine (3), and uridine (4) have been prepared chemically with {sup 13}C enrichment (99 atom %) at C1{prime} and C2{prime} of the ribose ring. Reliable synthetic protocols have been developed to permit access to millimole quantities of labeled ribonucleosides required for structural studies of stable isotopically labeled oligonucleotides and for in vivo metabolism studies. High-resolution {sup 1}H and {sup 13}C NMR spectra of the enriched ribonucleosides have been obtained, and {sup 13}C-{sup 13}C and {sup 13}C-{sup 1}H spin-coupling constants have been measured for pathways within the {beta}-D-ribofuranose ring and across the N-glycoside bond. Related couplings were determined in methyl {alpha}- and {beta}-D-riboruanosides (5,6), and in two conformationally constrained nucleosides, 2,2{prime}-anhydro-(1-{beta}-D-arabinofuranosyl)uracil (7) and 2{prime},3{prime}-O-isopropylidene-2,5{prime}-O-cyclouridine (8). The latter data were used to construct a crude Karplus curve for the {sup 13}C-C-N-{sup 13}C coupling pathway across the N-glycoside bond in 1-4. {sup 1}H-{sup 1}H, {sup 13}C-{sup 1}H, and {sup 13}C-{sup 13}C coupling data are used to evaluate current models describing the conformational dynamics of 1-4 in aqueous solution.

• OSTI ID: 5322526
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 112:20; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
BONDING
CARBOHYDRATES
CARBON 13
CARBON ISOTOPES
CHEMICAL PREPARATION
CONFORMATIONAL CHANGES
EVEN-ODD NUCLEI
FABRICATION
GLYCOSIDES
ISOTOPES
JOINING
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEIC ACIDS
NUCLEOSIDES
NUCLEOTIDES
ORGANIC COMPOUNDS
RESONANCE
RIBOSIDES
RNA
STABLE ISOTOPES
SYNTHESIS