Truxillines are a group of tropane alkaloids present in coca leaves that are formed by photochemical dimerization of cinnamoylcocaine(s). Proportion of different truxilline forms present in cocaine serves as its geographical, manufacture, and storage "fingerprint"; thus, the quantitative determination of truxilline content represents one of the powerful methods of analysis and characterization of cocaine samples. Contrary to the statements repeatedly presented in the literature, namely, that there exist exactly 11 truxillines and that every single truxilline is diastereomer of any other, here we show that, in fact, a total of 15 truxillines exist, which can be divided in two structurally isomeric groups-five mutually diastereomeric truxillates and 10 mutually diastereomeric truxinates.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chir.23680 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Counting the truxillines-11 or more, the question is now.
Chirality
June 2024
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Zagreb, Croatia.
Truxillines are a group of tropane alkaloids present in coca leaves that are formed by photochemical dimerization of cinnamoylcocaine(s). Proportion of different truxilline forms present in cocaine serves as its geographical, manufacture, and storage "fingerprint"; thus, the quantitative determination of truxilline content represents one of the powerful methods of analysis and characterization of cocaine samples. Contrary to the statements repeatedly presented in the literature, namely, that there exist exactly 11 truxillines and that every single truxilline is diastereomer of any other, here we show that, in fact, a total of 15 truxillines exist, which can be divided in two structurally isomeric groups-five mutually diastereomeric truxillates and 10 mutually diastereomeric truxinates.
View Article and Find Full Text PDFHelicene-based π-conjugated macrocycles: their synthesis, properties, chirality and self-assembly into molecular stripes on a graphite surface.
Nanoscale
January 2023
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
Fully aromatic helicenes are attractive building blocks for the construction of inherently chiral π-conjugated macrocyclic nanocarbons. These hitherto rare molecular architectures are envisaged to exhibit remarkable (chir)optical properties, self-assembly, charge/spin transport, induced ring current or a fascinating Möbius topology. Here the synthesis of helically chiral macrocycles that combine angular dibenzo[5]helicene units as corners and linear -stilbene-4,4'-diyl linkers as edges is reported.
View Article and Find Full Text PDFChiral polymer hosts for circularly polarized electroluminescence devices.
Chem Sci
July 2021
Division of Chemical Engineering and Materials Science, Graduate Program in System Health Science and Engineering, Ewha Womans University Seoul 03760 Republic of Korea
Polymer electroluminescence devices producing circularly polarized luminescence (CP PLEDs) have valuable photonic applications. The fabrication of a CP PLED requires a polymer host that provides the appropriate chiral environment around the emitting dopant. However, chemical strategies for the design of chiral polymer hosts remain underdeveloped.
View Article and Find Full Text PDFDifferentiation and Quantification of Diastereomeric Pairs of Glycosphingolipids Using Gas-Phase Ion Chemistry.
Anal Chem
October 2020
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States.
Glycosphingolipids (GSLs), including lyso-glycosphingolipids (lyso-GSLs) and cerebrosides (HexCer), constitute a sphingolipid subclass. The diastereomerism between their monosaccharide head groups, glucose and galactose in mammalian cells, gives rise to an analytical challenge in the differentiation of their biological roles in healthy and disease states. Shotgun tandem mass spectrometry has been demonstrated to be a powerful tool in lipidomics analysis in which the differentiation of the diastereomeric pairs of GSLs could be achieved with offline chemical modifications.
View Article and Find Full Text PDFBiconcave and Convex-Concave Tribenzotriquinacene Dimers.
J Org Chem
April 2018
Department of Chemistry and Center for Molecular Materials (CM2) , Bielefeld University, 33615 Bielefeld , Germany.
A new chiral tribenzotriquinacene bearing an ortho-bromoaniline nucleus was synthesized and optically resolved. The individual enantiomers, the absolute configuration of which was confirmed by single-crystal X-ray structure analysis, were stereoselectively converted into the same pyrazine-fused syn-bis-TBTQ derivative by chirality-assisted Buchwald-Hartwig amination. The corresponding diastereomeric anti-dimer was obtained alongside the syn-dimer from the racemic sample under similar reaction conditions.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!