Citalopram (CIT) is a highly selective serotonin reuptake inhibitor (SSRI) frequently used in the treatment of major depressive disorders. It has a chiral centre in its structure and is used in therapy both as a racemic mixture (R,S-CIT) and a pure enantiomer (S-CIT). The differences between the pharmacokinetic and pharmacological profiles of the two enantiomers are well established. Consequently, the development of new efficient chiral analysis methods for their enantiomeric separation is a topic of great actuality. CIT metabolism is stereoselective as it is metabolized in chiral active metabolites, which retain considerable SSRI activity and contribute to the pharmacological effect. Chiral analytical methods are employed for the determination of enantiomeric ratio in pharmaceutical preparations and for monitoring the enantiomer levels in biological samples for therapeutic and toxicologic purposes. The current study reviews the published literature for the chiral analysis of CIT and its metabolites based on chromatographic and electrophoretic methods coupled with UV, fluorescence and mass spectrometry detectors.
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http://dx.doi.org/10.1002/chir.23139 | DOI Listing |
Nat Chem
January 2025
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Institut de Química Computacional i Catàlisi (IQCC), Universitat de Girona, Maria Aurèlia Capmany 69, 17003 Girona, Spain.
Discrimination of enantiomeric substrate molecules is one of the fundamental properties of biological hosts. Replicating enantioselective molecular recognition with synthetic receptors is a topic of interest with implications in diverse applications such as bioinspired enantioselective catalysis, enantiomer separation, or sensing. In this review, five different systems reported in the literature are discussed, and their performance and versatility are analyzed.
View Article and Find Full Text PDFBiomed Chromatogr
February 2025
Department of Pharmaceutical Chemistry and Analysis, ISF College of Pharmacy, Moga, Punjab, India.
Enantioseparation and enantiorecognition are crucial in the pharmaceutical analysis of chiral substances, impacting safety, efficacy, and regulatory compliance. Enantioseparation refers to the process of separating enantiomers from a mixture, typically achieved through chromatography techniques like HPLC and SFC. In contrast, enantiorecognition involves the identification of enantiomers based on their interaction with a chiral selector without the need for separation.
View Article and Find Full Text PDFNat Commun
January 2025
School of Chemistry, Chemical Engineering, and Biotechnology, Nanyang Technological University, Singapore, 637371, Singapore.
Acylation stands as a fundamental process in both biological pathways and synthetic chemical reactions, with acylated saccharides and their derivatives holding diverse applications ranging from bioactive agents to synthetic building blocks. A longstanding objective in organic synthesis has been the site-selective acylation of saccharides without extensive pre-protection of alcohol units. In this study, we demonstrate that by simply altering the chirality of N-heterocyclic carbene (NHC) organic catalysts, the site-selectivity of saccharide acylation reactions can be effectively modulated.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.
We recently reported a chiral phosphoric acid (CPA) catalyzed enantioselective photomediated ring contraction of piperidines and other saturated heterocycles. By extruding a single heteroatom from a ring, this transformation builds desirable C(sp)-C(sp) bonds in the ring contracted products; however, the origins of enantioselectivity remain poorly understood. In this work, enantioselectivity of the ring contraction has been explored across an expanded structurally diverse substrate scope, revealing a wide range of enantioselectivities (0-99%) using two distinct CPA catalysts.
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