Limitations in the description of conformational preferences of C-disaccharides: The (1 -> 3)-C-mannobiose case

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00480867" target="_blank" >RIV/61388963:_____/17:00480867 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22330/17:43913463

Result on the web

<a href="http://dx.doi.org/10.1016/j.carres.2017.09.006" target="_blank" >http://dx.doi.org/10.1016/j.carres.2017.09.006</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.carres.2017.09.006" target="_blank" >10.1016/j.carres.2017.09.006</a>

Result language

angličtina

Original language name

Limitations in the description of conformational preferences of C-disaccharides: The (1 -> 3)-C-mannobiose case

Original language description

Conformational preferences of two C-glycosyl analogues of Manp-(1 -> 3)-Manp, were studied using a combined method of theoretical and experimental chemistry. Molecular dynamics was utilized to provide conformational behavior along C-glycosidic bonds of methyl 3-deoxy-3-C-[(alpha-D-mannopyranosyl) methyl]-alpha-D-and L-mannopyranosides. The OPLS2005 and Glycam06 force fields were used. Simulations were performed with explicit water (TIP3P) and methanol. Results were compared with a complete conformational scan at the MM4 level with the dielectric constant corresponding to methanol. In order to verify predicted conformational preferences, vicinal (3)J(HH) NMR coupling constants were calculated by the Karplus equation on simulated potential energy surfaces (PES). A set of new parameters for the Karplus equation was also designed. Predicted 3JHH were compared with experimental data. We also used reverse methodology, in which the (3)J(HH) coupling constants were calculated at the DFT level for each family of (phi, psi)-conformers separately and then experimental values were decomposed onto calculated (3)J(HH) couplings in order to obtain experimentally derived populations of conformers. As an alternative method of evaluation of preferred conformers, analysis of sensitive C-13 chemical shifts was introduced. We were able to thoroughly discuss several fundamental issues in predictions of preferred conformers of C-saccharides, such as the solvent effect, reliability of the force field, character of empirical Karplus equation or applicability of NMR parameters in predictions of conformational preferences in general.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10403 - Physical chemistry

Project

<a href="/en/project/GA16-00270S" target="_blank" >GA16-00270S: Elucidation of the structure and interactions of glycoconjugates and glycans using vibrational spectroscopy</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Carbohydrate Research

ISSN

0008-6215

e-ISSN

—

Volume of the periodical

451

Issue of the periodical within the volume

Nov 8

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

9

Pages from-to

42-50

UT code for WoS article

000413320300005

EID of the result in the Scopus database

2-s2.0-85029726149