Structure of heroin in a solution revealed by chiroptical spectroscopy
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F20%3A43920722" target="_blank" >RIV/60461373:22330/20:43920722 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22340/20:43920722 RIV/60461373:22810/20:43920722
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/chir.23196" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/chir.23196</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chir.23196" target="_blank" >10.1002/chir.23196</a>
Alternative languages
Result language
angličtina
Original language name
Structure of heroin in a solution revealed by chiroptical spectroscopy
Original language description
In this work, the 3-D structure of the well-known opioid drug heroin in a solution was investigated. The goal was to provide a complete and detailed description of the stable conformers with their relative abundances. This knowledge is very important from the pharmaceutical and forensic point of view as it could help significantly with deeper understanding of heroin's metabolism and the development of antagonist medicines for the case of an overdose. As heroin is a chiral compound with five stereogenic centres, the methods of chiroptical spectroscopy supplemented by density functional theory (DFT) calculations were applied to study its conformations in chloroform solution. The selected chiroptical methods, namely, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD), are inherently sensitive to the 3-D structure of small- to medium-sized chiral organic molecules. A thorough conformational analysis revealed four stable conformers of heroin in chloroform solution, where the conductor-like polarizable continuum model of the solvent was used for all the calculations. The simulated ultraviolet (UV), infrared (IR), ECD, and VCD spectra were compared with the experimental ones and very good agreement was found, which enabled a detailed structure description and interpretation of the spectra. Chiroptical spectroscopy in combination with DFT calculations proved to be a very sensitive tool for the analysis of the 3-D structure of heroin in a solution in contrast with conventional spectroscopic methods. Especially, the application of VCD seems to be a promising approach for monitoring structural changes, for instance, those caused by solvents or interactions with other agents. © 2020 Wiley Periodicals, Inc.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10406 - Analytical chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chirality
ISSN
0899-0042
e-ISSN
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Volume of the periodical
32
Issue of the periodical within the volume
6
Country of publishing house
US - UNITED STATES
Number of pages
12
Pages from-to
854-865
UT code for WoS article
000534457200010
EID of the result in the Scopus database
2-s2.0-85079885015