The optical rotatory dispersion of purine nucleosides

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

doi:10.1016/0006-291x(66)90303-2

Cited by 45 publications

(18 citation statements)

References 6 publications

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“…The structural formulas of the compounds studied are contained in Figure 1. sured in the uv region for 2',3',5,-trideoxyadenosine (I), 2', 3', 5 '-trideoxy-2', 3 '-didehydroadenosine (II), adenosine (III), 2',3 '-dideoxy-2 ',3'-didehydroadenosine (IV), 6-amino-9-(5'-S-ethyl-5'-thio-2',3',5'-trideoxy-2', 3 '-didehydro-^-D-^Zycero-pentofuranosyOpurine (V), and adenosine 5 '-monophosphate (VI), which are typical of the compounds studied and which will be emphasized in the Theory and Discussion sections. Among these compounds are three unsaturated furano-syládenine nucleosides.…”

Section: Resultsmentioning

confidence: 99%

Vicinal effects on the optical activity of some adenine nucleosides

Miles¹,

Hahn²,

Robins³

et al. 1968

J. Phys. Chem.

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The optical rotatory dispersion, absorption, and, in some cases, the circular dichroism of some adenine nucleosides having diverse substituents in the carbohydrate ring have been examined. Solvent and temperature studies have also been performed when possible. Explanations for the changes in rotation with substituent are sought through theoretical means in correlation with available structural information. The changes in the 260-mfi Cotton effect lxoduced by the introduction of new s-electron systems can be accounted for quantitatively.

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Section: Resultsmentioning

confidence: 99%

Vicinal effects on the optical activity of some adenine nucleosides

Miles¹,

Hahn²,

Robins³

et al. 1968

J. Phys. Chem.

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“…It is clear from Table I that H-8 interacts with only H-l' in the cyclonucleoside 5 and is noninteracting with H-2' and H-3' in that same model. It is also seen that H-8 interacts with H-l', H-2', H-5', and/or H-5" in the guanosine model (3). It is clear from the results tabulated for isopropylideneadenosine that H-8 and H-l' interact.…”

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confidence: 85%

Conformation of nucleosides and nucleotides. Application of the nuclear Overhauser effect

Hart¹,

Davis²

1969

J. Am. Chem. Soc.

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“…Most studies in this area in the past have been empirical in nature. In a series of short communications [123][124][125][126] and a full paper [127], Ulbricht et al have re ported an extensive survey on the ORD properties of a large number of nucleosides, especially pyrimidine nucleosides. This rule predicts that the a-D configuration of a pair of anomeric glycosides is more dextrorotatory than the corresponding ^-configuration.…”

Section: The Ord-cd Studymentioning

confidence: 99%

“…Ulbricht and co-workers [126,127,142,143] proposed that the CD (or ORD) spectra of the /3-D pyrimidine nucleosides and fi-D purine nucleosides indicate that these compounds are in and conformation. They argued that, in order to have an observable optical activity, the geometry of the chromophore must be more or less fixed with respect to an asymmetric environment; thus the rotation of the sugar-base torsion angle of the nucleoside must be restricted.…”

Section: The Ord-cd Studymentioning

confidence: 99%