A rule for predicting the sign of the cotton effect in pyrimidine furanose nucleosides

Ulbricht, T. L. V.; Emerson, T. R.; Swan, R. J.

doi:10.1016/s0040-4039(00)75732-7

Cited by 21 publications

(9 citation statements)

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“…Optical rotatory dispersion studies of these compounds have shown that the pyrimidine derivatives have positive Cotton effects, and the purine compounds negative ones, associated with ultraviolet absorption in the 260-280 mp region [23-261. However, the sign of the Cotton effect also depends on the conformation about the glycosidic linkage in the nucleoside molecule. This has been shown most clearly i n the case of pyrimidine nucleosides, in which a positive Cotton effect is associated with the anti conformation ; pyrimidine nucleosides fixed in the syn conformation have a negative Cotton effect [24]. Pyrimidine nucleosides have the anti conformation in solution owing to certain steric interactions, which restrict free rotation about the glycosidic bond [27].…”

Section: Discussionmentioning

confidence: 99%

“…poly (dC) and in the pH 3 form of DNA is associated with guanosine and not with cytidine residues is clearly shown by comparing them with the results on the protonation of guanine nucleosides [9], the 5'-GMP gel [50], poly (G) [53] and poly (dG) [54] which all show a peak in this region. Cytosine nucleosides [23,24], even protonated, poly (C) [17,33] and poly (dC) [33], on the other hand show strong negative rotations in this wavelength region. This is 2 In preliminary experiments we have followed the carefully controlled reaction of DNA with nitrous acid a t pH3.1.…”

Section: Discussionmentioning

confidence: 99%

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Protonated Polynucleotide Structures

Courtois

Fromageot

Guschlbauer

1968

European Journal of Biochemistry

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1. The change of the optical rotatory dispersion spectra as a function of pH of DNAs of different base composition and the synthetic polynucleotides poly d(A-T) and poly (dG) * poly (dC) has been studied.2. It is shown that the acid titration of DNA when followed by optical rotatory dispersion is considerably more complex than it appears from ultraviolet absorption data. The gradual appearance of a peak at 260-270 mp between pH 3 and 4 before acid denaturation, indicates a change of conformation of the guanosine residues in this pH region.3. DNA methylated in N-7 of guanine does not show this inversion of Cotton effects. It is concluded that this position plays an important role in the acid titration of DNA.4. Protonation on N-7 of guanine, rotation of guanine out of the helix, reversion into the synposition, pairing in Hoogsteen manner and thus sharing the proton with N-1 on cytosine is suggested as a possible interpretation of these results. 5.From the data presented it is concluded that poly (dG) . poly (dC) has a conformation and/or structure merent from that of DNA (B-form). In analogy with published data on nucleosides, it is suggested that guanosine is in the syn-conformation. Three possible structures seem to be feasible: Nearly all of the many investigations on the titration behaviour of DNA have attributed the accompanying phenomena to the protonation of cytidine residues [l-61. Since most of these results are based primarily upon ultraviolet absorbance changes, it appears legitimate to ask, (a) if other bases than cytidine could behave in such a way as to cause similar spectral changes [7,8] and thus take part in the protonation of DNA, and (b) if ultraviolet spectrophotometry in general is a sensitive enough technique to study the problem of DNA titration.Recent work on the optical properties of dGMP this study was in progress our attention was drawn to two preliminary communications by Luck and Zimmer [13] concerning this additional Cotton effect at about 265 mp which is studied in more detail in the present paper. The data presented here indicate that guanine is at least partly responsible for the titration behaviour of DNA. Preliminary evidence is further presented for an original structure for poly (dG) -poly (dC) different from that of DNA. The results on the titration behaviour of DNA point to the fact that an intermediary structure at about pH3.0 (in 0.15M Na+) is formed which is partially protonated and where the deoxyguanosine possibly assumed a conformation similar to that in poly (dG) -poly (dC) .

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Protonated Polynucleotide Structures

Courtois

Fromageot

Guschlbauer

1968

European Journal of Biochemistry

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“…Water temperature (9) and available sunlight (10,11) have been the factors most frequently suggested as controlling coral growth rates. A recent study in Hawaii (11) has indicated that available light is a dominant factor in determining growth rates of reef corals there.…”

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confidence: 99%

“…The structure of these compounds was established by elemental analysis (9) and spectral analysis. The cyclonucleotide and its morpholino precursor exhibited the characteristic absorption maxima at 250 to 252 nm (5) and a negative Cotton effect (10).…”

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Oligothymidylates: Formation by Thermal Condensation of O ² ,5′-Cyclothymidine 3′-Phosphate

Nagyvary

Nagpal

1972

Science

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Reaction of 1‐(2′,3′‐epoxy‐β‐D‐lyxofuranosyl)uracil with hydrogen fluoride. The unexpected formation of 1‐(3′‐fluoro‐3′‐deoxy‐β‐D‐ribofuranosyl)uracil

Misra

Gati

Knaus

et al. 1984

Journal of Heterocyclic Chem

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A rule for predicting the sign of the cotton effect in pyrimidine furanose nucleosides

Cited by 21 publications

References 5 publications

Protonated Polynucleotide Structures

Protonated Polynucleotide Structures

Oligothymidylates: Formation by Thermal Condensation of O ² ,5′-Cyclothymidine 3′-Phosphate

Reaction of 1‐(2′,3′‐epoxy‐β‐D‐lyxofuranosyl)uracil with hydrogen fluoride. The unexpected formation of 1‐(3′‐fluoro‐3′‐deoxy‐β‐D‐ribofuranosyl)uracil

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A rule for predicting the sign of the cotton effect in pyrimidine furanose nucleosides

Cited by 21 publications

References 5 publications

Protonated Polynucleotide Structures

Protonated Polynucleotide Structures

Oligothymidylates: Formation by Thermal Condensation of O 2 ,5′-Cyclothymidine 3′-Phosphate

Reaction of 1‐(2′,3′‐epoxy‐β‐D‐lyxofuranosyl)uracil with hydrogen fluoride. The unexpected formation of 1‐(3′‐fluoro‐3′‐deoxy‐β‐D‐ribofuranosyl)uracil

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Oligothymidylates: Formation by Thermal Condensation of O ² ,5′-Cyclothymidine 3′-Phosphate