Absolute Configuration Determination of a Taxol Precursor Based on Raman Optical Activity Spectra

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475018" target="_blank" >RIV/61388963:_____/17:00475018 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11320/17:10371355

Výsledek na webu

<a href="http://dx.doi.org/10.1021/acs.jpcb.6b12318" target="_blank" >http://dx.doi.org/10.1021/acs.jpcb.6b12318</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jpcb.6b12318" target="_blank" >10.1021/acs.jpcb.6b12318</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Absolute Configuration Determination of a Taxol Precursor Based on Raman Optical Activity Spectra

Popis výsledku v původním jazyce

Enantiomeric purity of drugs is essential for their biological activity. In the present study, we investigate the performance of Raman optical activity (ROA) spectroscopy in distinguishing four possible stereoisomers of the synthetic precursor used for the production of taxol from baccatin III. Taxol is one of the best-selling medicaments used in the treatment of ovarian, lung, and breast cancers and Kaposi's sarcoma. In a low yield, it may be isolated from the bark of the Pacific yew tree (Taxus brevifolia), however, its industrial production is largely dependent on the precursor. It is shown that for reliable comparison of the experimental and computed Raman and ROA intensities a large number of conformers had to be averaged, to properly account for molecular flexibility in solution. In addition, if combined with the density functional theory computations, ROA spectra provide convenient and economic means of absolute configuration determination.

Název v anglickém jazyce

Absolute Configuration Determination of a Taxol Precursor Based on Raman Optical Activity Spectra

Popis výsledku anglicky

Enantiomeric purity of drugs is essential for their biological activity. In the present study, we investigate the performance of Raman optical activity (ROA) spectroscopy in distinguishing four possible stereoisomers of the synthetic precursor used for the production of taxol from baccatin III. Taxol is one of the best-selling medicaments used in the treatment of ovarian, lung, and breast cancers and Kaposi's sarcoma. In a low yield, it may be isolated from the bark of the Pacific yew tree (Taxus brevifolia), however, its industrial production is largely dependent on the precursor. It is shown that for reliable comparison of the experimental and computed Raman and ROA intensities a large number of conformers had to be averaged, to properly account for molecular flexibility in solution. In addition, if combined with the density functional theory computations, ROA spectra provide convenient and economic means of absolute configuration determination.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA16-05935S" target="_blank" >GA16-05935S: Kombinace klasických a kvantově-mechanických výpočetních technik pro vibrační optickou aktivitu</a><br>

Návaznosti

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

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Journal of Physical Chemistry B

ISSN

1520-6106

e-ISSN

—

Svazek periodika

121

Číslo periodika v rámci svazku

7

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

8

Strana od-do

1544-1551

Kód UT WoS článku

000394925700009

EID výsledku v databázi Scopus

2-s2.0-85027280483