The Structure of 2-Deoxy-ribose.

Furberg, Sven; Hjortaas, K. E.; Lindgren, Jan‐Erik; Varde, E.; Westin, Gertrud

doi:10.3891/acta.chem.scand.14-1357

Cited by 28 publications

(14 citation statements)

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“…Experiments with 2-deoxy-D-ribose conducted with L. Anderson confirmed the X-ray evidence (20) for the P-pyranose form in the crystals, m.p. 77-84", [a];' -97" -) -48" after 20 lnin ( c , 2 in water).…”

Section: 4--'supporting

confidence: 50%

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The Proton Magnetic Resonance Spectra and Tautomeric Equilibria of Aldoses in Deuterium Oxide

Lemieux¹,

Stevens²

1966

Can. J. Chem.

347

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The proton magnetic resonance spectra of D-sylose, D-lyxose, n-arabinose, D-ribose, D -~~L I C O S~, n-mannose, and D-galactose were determined a t 100 Mc.p.s. in deuteriu~ri oxide. 'I'he chemical shifts and structures of a number of ring protons in these compounds were determined either by spin-deco~~pling experiments or by synthesis of specifically deuterated compounds. 'I'he proton magnetic resonance parameters are shown to provide considerable information on the conformations and tautonleric equilibria for the sugars in aqueo~ls solution. I t is concluded that, for aldoppranoses in a chair conformation, the chemical shift of equatorial protons a t a given position is virtually independent of configurational changes a t other positions. However, an axial proton is shielded about 0.3 p.p.111. less by an axial hydrosyl group a t a neighboring position than when the hydroxyl group is in an equatorial orientation. An axial hydrosyl group leads to deshielding of a n opposing axial proton b y about 0.35 p.p.m. By using the chemical shifts of the ring protons of @-D-xylopyranose and @ -D -~~u c o~~~~I I o s~ as reference point, the chernical shifts of protons in other pyranose structures could be anticipated to within a useful . . degree of accuracy.Lvidence was obtained that D-ribose and 2-deoxv-D-ribose esist in aqueous s o l u t i o~~ both in the pyranose and in the furanose forms. None of the other pentoses showed readily detectable anlounts of the furanose forrns a t equilibrium. rllthough D-allose does not give readily detectable alnounts of the furanose forms \vhen a t equilibriunl in aqueous solutions, n-altrose does. D-Talose showed only two forms, one of which was the @-pyranose structure.Lenz and Heeschen (I) examined the nuclear magnetic resonance (n.111.r.) spectra of D-glucose, D-mannose, 2-deoxy-D-glucose, and D-xylose with deuterium oxide as solvent. Only the signals of the anomeric protons were readily observed, and the spacings of these signals were used as coupling constants to estiillate conformational features for these sugars in aqueous solution. The observed spacings \\rere undoubtedly strongly influenced by virtual long-range coupling (2, 3) and, therefore, were not a direct measure of the coupling constants involved. Also, it is now evident (4, 5) that the relationship bet~veen the coupling constant and the dihedral angle defined by neighboring protons (the Ixarplus relationship) is subject to parameters other than the dihedral angle. Therefore, attempts to relate the spacings of the doublet signals for the anomeric protons of sugars t o precise molecular geometry are without either a theoretical or an empirical basis. Althougll coupling constants between neighboring protons cannot be used to predict precise conformational features, their use in appropriate instances for establishing configurationa1 features (6) remains unchallenged.Use has also been made of chemical shifts for establishing the configurations of sugars

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Section: 4--'supporting

confidence: 50%

“…with a spacing of 3.5 c.p.s. Certainly, therefore, the compound must exist, a t least to a substantial extent, in the C1-conformation which is present in the crystalline solid (20). T h e furanose forms gave signals for the anomeric protoils of about equal intensity a t 5.…”

Section: 4--'mentioning

confidence: 99%

The Proton Magnetic Resonance Spectra and Tautomeric Equilibria of Aldoses in Deuterium Oxide

Lemieux¹,

Stevens²

1966

Can. J. Chem.

347

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“…The molecule adopts the chair conformation with hydroxyl groups at CI and C4 being at axial positions and that attached to C3 in equatorial position. As such, the structure is similar to that elucidated previously from projections with limited data sets [8]. The orientation of the molecules in the unit cell, however, differs substantially.…”

Section: A) Crystallographysupporting

confidence: 79%

Crystal Structure and the Radiation-Induced Free-Radical Chain Reaction of 2-Deoxy-β-D-erythro-pentopyranose in the Solid State

Schuchmann

Sonntag

Tsay

1981

Zeitschrift Für Naturforschung B

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Abstract The crystal structure of 2-deoxy-β-D-enrythro-pentopyranose (1) was reexamined by X-ray crystallographic studies. In crystalline 1, a radiation-induced chain reaction occurs with the only product being, 2,5-dideoxy-D-enrythro-pentonic acid (4). In the chain propagating step leading to 4, an H atom is transferred over a distance of ≤ 3.3 Å as taken from interatomic distances in the unperturbed crystal. The crystal structure clearly indicates the direction by which the chain reaction proceeds through the crystal. The strong temperature dependence of G(4) is discussed in terms of temperature effects on chain initiation, propagation and termination rates.

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“…32c) [210,[233][234][235]. Former experiments to determine the conformation of monosaccharides based on X-ray and NMR [233,234,236,237] are influenced by environmental effects associated with the solvent or crystal lattice. An IR spectrum of 2DR isolated in an inert matrix [238] has been interpreted by summing the modeled spectra for several α and β conformers.…”

Section: -Deoxy-d-ribose and Ribosementioning

confidence: 99%

Microwave Spectroscopy of Biomolecular Building Blocks

Alonso

López

2014

Topics in Current Chemistry

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Microwave spectroscopy, considered as the most definitive gas phase structural probe, is able to distinguish between different conformational structures of a molecule, because they have unique spectroscopic constants and give rise to distinct individual rotational spectra.Previously, application of this technique was limited to molecular specimens possessing appreciable vapor pressures, thus discarding the possibility of studying many other molecules of biological importance, in particular those with high melting points, which had a tendency to undergo thermal reactions, and ultimately degradation, upon heating.Nowadays, the combination of laser ablation with Fourier transform microwave spectroscopy techniques, in supersonic jets, has enabled the gas-phase study of such systems. In this chapter, these techniques, including broadband spectroscopy, as well as results of their application into the study of the conformational panorama and structure of biomolecular building blocks, such as amino acids, nucleic bases, and monosaccharides, are briefly discussed, and with them, the tools for conformational assignation - rotational constants, nuclear quadrupole coupling interaction, and dipole moment.

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The Structure of 2-Deoxy-ribose.

Cited by 28 publications

References 0 publications

The Proton Magnetic Resonance Spectra and Tautomeric Equilibria of Aldoses in Deuterium Oxide

The Proton Magnetic Resonance Spectra and Tautomeric Equilibria of Aldoses in Deuterium Oxide

Crystal Structure and the Radiation-Induced Free-Radical Chain Reaction of 2-Deoxy-β-D-erythro-pentopyranose in the Solid State

Microwave Spectroscopy of Biomolecular Building Blocks

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