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Titolo:
(N-15(5))-labeled adenine derivatives: Synthesis and studies of tautomerism by N-15 NMR spectroscopy and theoretical calculations
Autore:
Laxer, A; Major, DT; Gottlieb, HE; Fischer, B;
Indirizzi:
Bar Ilan Univ, Dept Chem, Gonda Goldschmied Med Res Ctr, IL-52900 Ramat Gan, Israel Bar Ilan Univ Ramat Gan Israel IL-52900 Ctr, IL-52900 Ramat Gan, Israel
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 16, volume: 66, anno: 2001,
pagine: 5463 - 5481
SICI:
0022-3263(20010810)66:16<5463:(ADSAS>2.0.ZU;2-N
Fonte:
ISI
Lingua:
ENG
Soggetto:
NUCLEAR-MAGNETIC-RESONANCE; MOLECULAR-ORBITAL METHODS; CONTINUUM DIELECTRIC THEORY; DENSITY-FUNCTIONAL THEORY; GAUSSIAN-BASIS SETS; NITROGEN-15-LABELED DEOXYNUCLEOSIDES; MATRIX-ISOLATION; N-15-LABELED NUCLEOSIDES; DIMROTH-REARRANGEMENT; ORGANIC-MOLECULES;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
104
Recensione:
Indirizzi per estratti:
Indirizzo: Fischer, B Bar Ilan Univ, Dept Chem, Gonda Goldschmied Med Res Ctr, IL-52900 Ramat Gan, Israel Bar Ilan Univ Ramat Gan Israel IL-52900 900 Ramat Gan, Israel
Citazione:
A. Laxer et al., "(N-15(5))-labeled adenine derivatives: Synthesis and studies of tautomerism by N-15 NMR spectroscopy and theoretical calculations", J ORG CHEM, 66(16), 2001, pp. 5463-5481

Abstract

Since the nitrogens of nucleosides and nucleotides play an important role in the molecular recognition of these compounds, N-15 NMR became a method of choice in this field. Fully N-15-labeled adenine, required in the latter studies, was obtained in four synthetic steps, in a good yield. Likewise, (N-15(5))-2-hexylthioether-adenine and (N-15(5))-8-Br-adenine were obtained in five synthetic steps from the relatively inexpensive N-15 sources: N-15-NH4Cl, N-15-NH4OH, N-15-NaNO2. Full N-15 labeling of these adenine prototypes enabled to obtain high-resolution 15N NMR spectra of these bases at 60.8MHz. Furthermore, the spectra suggested the existence of the N3-H species in the tautomeric mixtures of these compounds in solution, in addition to the well-reported N9-H (major) and N7-H (minor) tautomers. These observations were also supported by quantum mechanical calculations of the tautomeric equilibria in the gas phase and in solution of the above-mentioned adenine compounds. The gas-phase tautomeric equilibria were estimated using densityfunctional theory and second-order perturbation theory methods. Solvent effects were included by means of both continuum and discrete solvation models. The observation of the existence of the N3-H tautomer has a clear impacton the possible H-bonding patterns of these adenine prototypes and on their molecular recognition by various biological macromolecules. The above(15)N-labeled analogues are expected to find use as N-15 NMR probes for numerous biochemical studies.

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Documento generato il 03/07/20 alle ore 22:39:23