Über die Eigenschaften von polynucleotiden, welche uridin und 4-thiouridin enthalten

Scheit, K. H.; Gaertner, E

doi:10.1016/0005-2787(69)90514-0

Cited by 36 publications

(3 citation statements)

References 6 publications

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“…Modification of cytosine base to phosphorus-containing cytosine analogues, diphosphocytosine, is a good start point in this topic. Also, their existence in many tautomeric forms, like other nucleoside bases, seems to be crucial in order to explain the mutation occurring during DNA duplication [63][64][65][66]. Searching the literatures confirms that no previous studies include all numbers of cytosine tautomers.…”

Section: Introductionmentioning

confidence: 76%

Structure and Stability of Chemically Modified DNA Bases: Quantum Chemical Calculations on 16 Isomers of Diphosphocytosine

Al‐Sehemi

El-Gogary

Wolschann

et al. 2013

ISRN Physical Chemistry

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We studied for the first time 16 tautomers/rotamers of diphosphocytosine by four computational methods. Some of these tautomers/rotamers are isoenergetic although they have different structures. High-level electron correlation MP2 and MP4(SDQ) ab initio methods and density functional methods employing a B3LYP and the new M06-2X functional were used to study the structure and relative stability of 16 tautomers/rotamers of diphosphocytosine. The dienol tautomers of diphosphocytosine are shown to be much more stable than the keto-enol and diketo forms. The tautomers/rotamers stability could be ranked as PC3 = PC12 < PC2 = PC11 < PC1 < PC10 < PC8 < PC9 < PC15 < PC16 < PC6 ∼ PC7 < PC13 < PC4 ∼ PC14 < PC5. This stability order was discussed in the light of stereo and electronic factors. Solvation effect has been modeled in a high dielectric solvent, water using the polarized continuum model (PCM). Consideration of the solvent causes some reordering of the relative stability of diphosphocytosine tautomers: PC3 ∼ PC12 ∼ PC2 ∼ PC11 < PC1 < PC10 < PC8 < PC9 < PC15 ∼ PC16 < PC13 < PC6 ∼ PC7 ∼ PC14 < PC4 ∼ PC5.

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Section: Introductionmentioning

confidence: 76%

Structure and Stability of Chemically Modified DNA Bases: Quantum Chemical Calculations on 16 Isomers of Diphosphocytosine

Al‐Sehemi

El-Gogary

Wolschann

et al. 2013

ISRN Physical Chemistry

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“…The ability of thiopyrimidine residues to stabilize the secondary structure of polynucleotides has been attributed to enhanced base-stacking interactions induced by the sulfur substituents (Faerber, Scheit & Sommer, 1972;Scheit & Gaertner, 1969;Bahr, Faerber & Scheit, 1973). Recent reviews have suggested that the bases in crystal structures of thiopyrimidines generally exhibit characteristic stacking patterns that involve intimate contacts between the sulfur substituent of one base and the ring systems of neighboring bases (Saenger, 1973;Saenger & Suck, 1973).…”

Section: Introductionmentioning

confidence: 99%

Stacking patterns of thiopyrimidines: the crystal structure of 2-thiocytosine picrate

DeLucas¹,

Hearn²,

Bugg³

1977

Acta Crystallogr Sect B

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P thermal ellipsoids might have the following explanation. From the estimated H atom positions of the r/-CsH 5 group, Fig. 2, it appears that the surroundings of the P atoms are quite different, and distances from P(2) to H(I) and H(2), 3.35 and 3.00 A, are longer than those from P(1) to H(1) and H(2), 3.00 and 2.45 A. The vibration of P(l) is, therefore, restricted while P(2) is free to move. CARRUTHERS, J. R. (1976 The structure was solved by use of 2305 symmetry-independent reflections measured on a diffractometer, and was refined by least squares to R = 0.091. The crystal structure consists of ribbons of stacked thiocytosine cations hydrogen-bonded to the picrate anions and to neighboring thiocytosine moieties. No stacking interactions were observed between thiocytosine cations and picrate anions.

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“…The unusual physical properties of these polynucleotides [3][4][5][6] suggested the investigation of polynucleotides containing 2,4-dithiouridine. This communication reports the molecular and crystal structure and spectral properties of 2,4-dithiouridine ( fig.…”

Section: Introductionmentioning

confidence: 99%

Structural and spectral properties of 2,4‐dithiouridine

1970

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Über die Eigenschaften von polynucleotiden, welche uridin und 4-thiouridin enthalten

Cited by 36 publications

References 6 publications

Structure and Stability of Chemically Modified DNA Bases: Quantum Chemical Calculations on 16 Isomers of Diphosphocytosine

Structure and Stability of Chemically Modified DNA Bases: Quantum Chemical Calculations on 16 Isomers of Diphosphocytosine

Stacking patterns of thiopyrimidines: the crystal structure of 2-thiocytosine picrate

Structural and spectral properties of 2,4‐dithiouridine

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