Circular dichroism of nucleoside derivatives. V. Cytosine derivatives

Miles, Daniel W.; Robins, Morris J.; Robins, Roland K.; Winkley, Michael W.; Eyring, Henry

doi:10.1021/ja01032a006

Cited by 81 publications

(25 citation statements)

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“…[29][30][31][32] This syn-anti equilibrium is affected by sugar puckering and modifications. [33][34][35] The phosphorylation of O5′ increases the interaction between O5′ and a base, which increases C3′-endo in sugar puckering, followed by an increase of the anti conformation. 36,37 In guanine nucleotides, the interaction between the amino group at the C2-position and the 5′-phosphate stabilizes the syn conformation.…”

Section: Nucleotide Conformations Of Syn and Antimentioning

confidence: 99%

The Structural Basis of the Kinetic Mechanism of a Gap-Filling X-Family DNA Polymerase That Binds Mg2+-dNTP Before Binding to DNA

Nakane

Ishikawa

Nakagawa

et al. 2012

Journal of Molecular Biology

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Section: Nucleotide Conformations Of Syn and Antimentioning

confidence: 99%

The Structural Basis of the Kinetic Mechanism of a Gap-Filling X-Family DNA Polymerase That Binds Mg2+-dNTP Before Binding to DNA

Nakane

Ishikawa

Nakagawa

et al. 2012

Journal of Molecular Biology

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“…52 No evidence has been found for n → π* transitions, which are predicted to have very small oscillator strengths. However, a weak feature around 5.0 eV in circular dichroism spectra 55 has been interpreted to be the transition from the ground state to the lowest singlet 1 A″(n → π*) state of the molecule. 52 In the present work, the EEL spectra should differ in many aspects from those recorded under optical conditions.…”

Section: A Electronic Excitationsmentioning

confidence: 99%

Absolute cross sections for electronic excitations of cytosine by low energy electron impact

Bazin

Michaud

Sanche

2010

The Journal of Chemical Physics

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The absolute cross sections (CS) for electronic excitations of cytosine by electron impact between 5 and 18 eV were measured by electron-energy loss (EEL) spectroscopy of the molecule deposited at low coverage on an inert Ar substrate. The lowest EEL features found at 3.55 and 4.02 eV are ascribed to transitions from the ground state to the two lowest triplet 1 3 A′(π→π*) and 2 3 A′ (π→π*) valence states of the molecule. Their energy dependent CS exhibit essentially a common maximum at about 6 eV with a value of 1.84 × 10 −17 cm 2 for the former and 4.94 × 10 −17 cm 2 for the latter. In contrast, the CS for the next EEL feature at 4.65 eV, which is ascribed to the optically allowed transition to the 2 1 A′(π→π*) valence state, shows only a steep rise to about 1.04 × 10 −16 cm 2 followed by a monotonous decrease with the incident electron energy. The higher EEL features at 5.39, 6.18, 6.83, and 7.55 eV are assigned to the excitations of the 3 3, 1 A′(π→π*), 4 1 A′(π→π*), 5 1 A′(π→π*), and 6 1 A′(π→π*) valence states, respectively. The CS for the 3 3, 1 A′ and 4 1 A′ states exhibit a common enhancement at about 10 eV superimposed on a more or less a steep rise, reaching respectively a maximum of 1.27 and 1.79 × 10 −16 cm 2 , followed by a monotonous decrease. This latter enhancement and the maximum seen at about 6 eV in the lowest triplet states correspond to the core-excited electron resonances that have been found by dissociative electron attachment experiments with cytosine in the gas phase. The weak EEL feature found at 5.01 eV with a maximum CS of 3.8 × 10 −18 cm 2 near its excitation threshold is attributed to transitions from the ground state to the 1 3, 1 A″(n→π*) states. The monotonous rise of the EEL signal above 8 eV is attributed to the ionization of the molecule. It is partitioned into four excitation energy regions at about 8.55, 9.21, 9.83, and 11.53 eV, which correspond closely to the ionization energies of the four highest occupied molecular orbitals of cytosine. The sum of the ionization CS for these four excitation regions reaches a maximum of 8.1 × 10 −16 cm 2 at the incident energy of 13 eV.

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“…The conformation about the glycosidic bond of 2-Me and 6-Me NAD ÷ may be safely deduced from the results of studies on the conformation of cytidine [14] and uridine [14][15][16] and their C-6 methyl analogues [14,17,18]. Cytidine and uridine exist in the anti conformation in solution [14][15][16] whereas 6-methylcytidine and 6-methyluridine are syn under the same conditions [14,17,18]. In the crystalline state, cytidine isanti [19] and 6-methyluridine syn [20] (same results as in solution).…”

Section: Resultsmentioning

confidence: 99%

Conformation about the glycosidic bond: Ribose‐nicotinamide of NAD⁺ bound to some dehydrogenases

Biellmann

Samama

1974

FEBS Letters

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Circular dichroism of nucleoside derivatives. V. Cytosine derivatives

Cited by 81 publications

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The Structural Basis of the Kinetic Mechanism of a Gap-Filling X-Family DNA Polymerase That Binds Mg2+-dNTP Before Binding to DNA

The Structural Basis of the Kinetic Mechanism of a Gap-Filling X-Family DNA Polymerase That Binds Mg2+-dNTP Before Binding to DNA

Absolute cross sections for electronic excitations of cytosine by low energy electron impact

Conformation about the glycosidic bond: Ribose‐nicotinamide of NAD⁺ bound to some dehydrogenases

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Circular dichroism of nucleoside derivatives. V. Cytosine derivatives

Cited by 81 publications

References 0 publications

The Structural Basis of the Kinetic Mechanism of a Gap-Filling X-Family DNA Polymerase That Binds Mg2+-dNTP Before Binding to DNA

The Structural Basis of the Kinetic Mechanism of a Gap-Filling X-Family DNA Polymerase That Binds Mg2+-dNTP Before Binding to DNA

Absolute cross sections for electronic excitations of cytosine by low energy electron impact

Conformation about the glycosidic bond: Ribose‐nicotinamide of NAD+ bound to some dehydrogenases

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Conformation about the glycosidic bond: Ribose‐nicotinamide of NAD⁺ bound to some dehydrogenases