Study of Stereoselective Interactions of Carbamoylated Quinine and Quinidine with 3,5-Dinitrobenzoyl alpha-Amino Acids Using VCD Spectroscopy in the Region of C-H Stretching Vibrations

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F11%3A43881492" target="_blank" >RIV/60461373:22340/11:43881492 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/chir.20929" target="_blank" >http://dx.doi.org/10.1002/chir.20929</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chir.20929" target="_blank" >10.1002/chir.20929</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Study of Stereoselective Interactions of Carbamoylated Quinine and Quinidine with 3,5-Dinitrobenzoyl alpha-Amino Acids Using VCD Spectroscopy in the Region of C-H Stretching Vibrations

Popis výsledku v původním jazyce

The stereoselective complexation of tert-butylcarbamoyl quinine and tert-butylcarbamoyl quinidine selectors (SOs) with 3,5-dinitrobenzoyl (DNB) derivatives of D-and L-alpha amino acids (DNB-Ala, DNB-Val, DNB-Leu, and DNB-Ile) as well as achiral DNB-Gly has been studied by vibrational circular dichroism (VCD) spectroscopy in the spectral region of C-H stretching vibrations. All the complexes of SOs and sterically compatible enantiomers of derivatized amino acid selectands (SAs) showed induced circular dichroism (ICD) bands in the region of aromatic C-H stretching vibrations, indicating the occurrence of a pi-pi interaction between the aromatic moieties of SA and SO. To our knowledge, this is the first report in which a pi-pi interaction was observed byVCD spectroscopy in this spectral region. No ICD bands were disclosed in the spectra of the sterically incompatible SA and SO complexes.

Název v anglickém jazyce

Study of Stereoselective Interactions of Carbamoylated Quinine and Quinidine with 3,5-Dinitrobenzoyl alpha-Amino Acids Using VCD Spectroscopy in the Region of C-H Stretching Vibrations

Popis výsledku anglicky

The stereoselective complexation of tert-butylcarbamoyl quinine and tert-butylcarbamoyl quinidine selectors (SOs) with 3,5-dinitrobenzoyl (DNB) derivatives of D-and L-alpha amino acids (DNB-Ala, DNB-Val, DNB-Leu, and DNB-Ile) as well as achiral DNB-Gly has been studied by vibrational circular dichroism (VCD) spectroscopy in the spectral region of C-H stretching vibrations. All the complexes of SOs and sterically compatible enantiomers of derivatized amino acid selectands (SAs) showed induced circular dichroism (ICD) bands in the region of aromatic C-H stretching vibrations, indicating the occurrence of a pi-pi interaction between the aromatic moieties of SA and SO. To our knowledge, this is the first report in which a pi-pi interaction was observed byVCD spectroscopy in this spectral region. No ICD bands were disclosed in the spectra of the sterically incompatible SA and SO complexes.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CB - Analytická chemie, separace

OECD FORD obor

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Projekt

<a href="/cs/project/IAA400550702" target="_blank" >IAA400550702: Spektroskopické a teoretické metody pro studium nekovaletních molekulových interakcí</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2011

Kód důvěrnosti údajů

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

Název periodika

Chirality

ISSN

0899-0042

e-ISSN

—

Svazek periodika

23

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

354-360

Kód UT WoS článku

000288087700011

EID výsledku v databázi Scopus

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