Related Experiment Video
Updated: May 28, 2026

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
Published on: September 17, 2017
Conformational preferences in diglycosyl disulfides: NMR and molecular modeling studies
Krisztina Fehér1, Richard P Matthews, Katalin E Kövér
1Department of Organic Chemistry, University of Debrecen, Pf. 20., H-4010 Debrecen, Hungary.
Abstract:
The conformations of several β1→β1' diglycosyl disulfides were investigated by NMR and computational methods. Experimental data, such as NOEs, proton-proton and proton-carbon-13 coupling constants, measured for solutions in DMSO, are in good agreement with values obtained by MD simulations in explicit DMSO. The disulfide torsion angles (C1-S-S-C1') preferentially sample values close to either +90° or -90° (+g or -g) and appear as the main metric that determines the conformational behavior of these glycomimetics. There is more conformational freedom around the C1-S and C1'-S' bonds (Φ and Ω torsions, respectively) and population cluster analysis allowed to identify up to four allowed conformational regions for each of the +g or -g forms. Population analysis of the hydroxylic group rotamers, based on proton-proton and proton-carbon-13 couplings as well as on calculated hydrogen bonding statistics, did not reveal any significant intramolecular hydrogen bonds in DMSO solution.
Related Concept Videos
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution
Newman Projections
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as conformers.
Stereoisomerism of Cyclic Compounds
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

