On the origin of the electronic and magnetic circular dichroism of naphthyl C-glycosides: Anomeric configuration

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00580580" target="_blank" >RIV/61388963:_____/24:00580580 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22330/24:43930082

Result on the web

<a href="https://doi.org/10.1016/j.carres.2023.109021" target="_blank" >https://doi.org/10.1016/j.carres.2023.109021</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.carres.2023.109021" target="_blank" >10.1016/j.carres.2023.109021</a>

Result language

angličtina

Original language name

On the origin of the electronic and magnetic circular dichroism of naphthyl C-glycosides: Anomeric configuration

Original language description

Aryl C-glycosides, in which the glycosidic bond is changed to a carbon-carbon bond, are an important family of biologically-active compounds. They often serve as secondary metabolites or exhibit antibiotic and cytostatic activities. Their stability to hydrolysis has made them attractive targets for new drugs. Their conformational behavior often strongly influences the resulting function. Their detailed structural and conformational description is thus highly desirable. This work studies the structure of three different naphthyl C-glycosides using UV-vis absorption as well as electronic and magnetic circular dichroism. It also describes their conformational preferences using a combination of molecular dynamics and DFT calculations. The reliability of these preferences has been verified by simulations of spectral properties and a comparison with their measured spectra. In particular, ECD spectroscopy has been shown to distinguish easily between alpha- and beta-pseudoanomers of aryl C-glycosides. Computer simulations and spectral decomposition have revealed how the resulting ECD patterns of the naphthyl glycosides studied are influenced by different conformer populations. In conclusion, reliable ECD patterns cannot be calculated by separating the naphthyl rotation from other conformational motions. MCD patterns have been similar for all the naphthyl C-glycosides studied. No clear diagnostic features have been found for either the pseudoanomeric configuration or the preferred hydroxymethyl rotamer. Nevertheless, the work has demonstrated the potential of MCD for the study of aryl glycosides interacting with proteins.

Czech name

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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

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2024

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

1873-426X

Volume of the periodical

535

Issue of the periodical within the volume

January

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

11

Pages from-to

109021

UT code for WoS article

001154687800001

EID of the result in the Scopus database

2-s2.0-85181672309