Conformational Populations of β-(1→4) O -Glycosidic Linkages Using Redundant NMR J -Couplings and Circular Statistics

Zhang, Wenhui; Turney, Toby; Meredith, Reagan; Pan, Qingfeng; Sernau, Luke; Wang, Xiaocong; Hu, Xiaosong; Woods, Robert J.; Carmichael, Ian; Serianni, Anthony S.

doi:10.1021/acs.jpcb.7b02252

Title: Conformational Populations of β-(1→4) O -Glycosidic Linkages Using Redundant NMR J -Couplings and Circular Statistics

Journal Article · 15 March 2017 · Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry

DOI: https://doi.org/10.1021/acs.jpcb.7b02252 · OSTI ID:1463134

Zhang, Wenhui ^[1]; Turney, Toby ^[1]; Meredith, Reagan ^[1]; Pan, Qingfeng ^[2]; Sernau, Luke ^[1]; Wang, Xiaocong ^[3]; Hu, Xiaosong ^[4]; Woods, Robert J. ^[3]; Carmichael, Ian ^[1];

^[1]

Univ. of Notre Dame, IN (United States)
Omicron Biochemicals Inc., South Bend, IN (United States)
Univ. of Georgia, Athens, GA (United States)
Wuhan Univ. of Technology (China)

Twelve disaccharides containing β-(1→4) linkages and displaying systematic structural variations in the vicinity of these linkages were selectively labeled with ¹³C to facilitate measurements of multiple NMR spin–spin (scalar; J) coupling constants (J_CH and J_CC values) across their O-glycosidic linkages. Ensembles of spin-couplings (²J_COC,³J_COCH, ³J_COCC) sensitive to the two linkage torsion angles, phi (Φ) and psi (ψ), were analyzed by using parametrized equations obtained from density functional theory (DFT) calculations, Fredholm theory, and circular statistics to calculate experiment-based rotamer populations for Φ and ψ in each disaccharide. With the statistical program MA’AT, torsion angles Φ and ψ were modeled as a single von Mises distribution, which yielded two parameters, the mean position and the circular standard deviation (CSD) for each angle. The NMR-derived rotamer populations were compared to those obtained from 1 μs aqueous molecular dynamics (MD) simulations and crystallographic database statistical analyses. Conformer populations obtained exclusively from the MA’AT treatment of redundant J-couplings were in very good agreement with those obtained from the MD simulations, providing evidence that conformational populations can be determined by NMR for mobile molecular elements such as O-glycosidic linkages with minimal input from theory. The approach also provides an experimental means to validate the conformational preferences predicted from MD simulations. The conformational behaviors of Φ in the 12 disaccharides were very similar, but those of ψ varied significantly, allowing a classification of the 12 disaccharides based on preferred linkage conformation in solution.

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Research Organization:: University of Notre Dame, IN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: FC02-04ER15533

OSTI ID:: 1463134

Journal Information:: Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry, Vol. 121, Issue 14; ISSN 1520-6106

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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