Elsevier

Carbohydrate Research

Volume 47, Issue 2, April 1976, Pages 311-314
Carbohydrate Research

Note
Conformation of the C-5/C-6 fragment of aldohexopyranoses

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  • Conformational study of the hydroxymethyl group in α-D-mannose derivatives

    2003, Tetrahedron Asymmetry
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    These results were explained in terms of both the gauche effect, which stabilizes the gg and gt rotamers, and the 1,3-syn interaction between O4 and O6, which destabilizes the tg rotamer. Although several conformational studies on the hydroxymethyl group of d-mannose derivatives have already been performed,6–9 we present here a systematic study of the influence of the aglycon and its absolute configuration on the populations of the hydroxymethyl group in two series of α-d-mannose derivatives: 2,3,4,6-tetrakis-O-acetyl- and 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-α-d-mannose, having different substituents at the anomeric carbon. On the basis of CD and NMR data the results show a dependence of the hydroxymethyl group rotational population on the aglycon and its absolute configuration, and that the gg or the gt rotamer has the highest population depending mainly on the aglycon.

  • Quantum mechanical and NMR spectroscopy studies on the conformations of the hydroxymethyl and methoxymethyl groups in aldohexosides

    2002, Carbohydrate Research
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    The same solutions were used, after D2O evaporation, to prepare CD3OD solutions. References for the chemical shifts were taken from standard values.2,37–40 H-6R and H-6S were assigned according to Gagnaire et al.41,42 and Ohrui et al.39,43 The use of a viscous solvent (D2O) with such concentrated solutions can cause line broadening due to relaxation phenomena and thus poorer resolution.

  • Conformation of a trimannoside bound to mannose-binding protein by nuclear magnetic resonance and molecular dynamics simulations

    2002, Biophysical Journal
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    A state with ω = 180° resulted in a linear molecule, whereas a state with ω = 60° resulted in a molecule bent by ∼80° at the II–III linkage. The ω = −60° state is known to be vanishingly populated in solution (De Bruyn and Anteunis, 1976), and this was confirmed based on measurements of three-bond coupling constants. Although such coupling constants for the bound state are not accessible in the types of experiment presented here, the combination of TrNOESY data and MD data presented also exclude a ω = −60° state for the bound conformation.

  • Solution conformations of a trimannoside from nuclear magnetic resonance and molecular dynamics simulations

    2000, Biophysical Journal
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    A DQF-COSY spectrum was able to provide unambiguous assignments for all protons except H5, H6, and H6′ of rings I and II. The stereospecific assignment of the two methylene protons attached to III-C6 was completed by comparing the relative magnitudes of the J couplings between H5 and these two methylene protons along with NOE-derived distance restraints (De Bruyn and Anteunis, 1976; Rao and Perlin, 1983). The assignment of all proton and 13C spins was completed through the use of 1H-13C HSQC and HMBC spectra.

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