A Symmetry Breaking in Design and Production of Enantiomeric Drugs

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 2981

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Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantynów 1F/117, 20-708 Lublin, Poland
Interests: asymmetric synthesis; synthesis of bidentant chiral ligands; fine organic synthesis; cross-metathesis reactions; CH activation; computer simulation of organic processes; some aspects of supramolecular chemistry
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Dear Colleagues,

Chirality, as a fundamental property of 3D objects (including many molecules and ions) to be non-superimposable on their mirror images, is imprinted on such basic building blocks of life as amino acids and sugars; it is further reflected by the chirality of more complex biochemical objects such as DNA, and finally, by the chirality of entire bodies. Each chiral compound exists as one of two possible isomeric molecules (or as a mixture of those two stereoisomers) that are related to one another as an object (e.g., right hand) and its mirror image (left hand). The biological properties of such optical isomers are often different: One of them could be a drug (e.g., (R)-(+)-thalidomide) but another a poison (e.g., (S)-(-)-thalidomide). Today, approximately 50% of marketed drugs are chiral. According to the U.S. Food and Drug Administration (FDA) policy, published in 1992, regarding single optical isomers (enantiomers), although both mixture and single optical isomeric drugs will continue to be developed, a higher proportion of single optical isomers are being submitted for new drug approval. The fundamental research enhances the understanding of the fine stereochemical mechanism of chemical processes that should help to design more efficient, cheaper, and more environmentally beneficial industrial methods of enantiomeric drug production. In this issue, we primarily focus on modern practical methods of symmetry breaking, which are of interest to the pharmaceutical industry, while manuscripts dedicated to the analysis of current status of the industry and the market of chiral drugs will also be considered for publication.

Prof. Dr. Oleh M. Demchuk
Guest Editor

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Keywords

  • Chiral drugs
  • Enantiomeric drug
  • Symmetry breaking
  • Origin of asymmetric induction
  • Pharmaceutical industry
  • Sereoselective industrial methods
  • Market of chiral drugs

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Published Papers (1 paper)

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Research

10 pages, 1877 KiB  
Article
A Chirality Chain in Phenylglycine, Phenylpropionic Acid, and Ibuprofen
by Henri Brunner, Takashi Tsuno and Gábor Balázs
Symmetry 2021, 13(1), 55; https://doi.org/10.3390/sym13010055 - 31 Dec 2020
Cited by 4 | Viewed by 2476
Abstract
Our strategy to analyze the structures of natural amino acids with respect to the interaction of three different elements of chirality within the molecules was applied to the non-natural amino acid (S)-α-phenylglycine, its analogue (S)-α-phenylpropionic acid, and the drug [...] Read more.
Our strategy to analyze the structures of natural amino acids with respect to the interaction of three different elements of chirality within the molecules was applied to the non-natural amino acid (S)-α-phenylglycine, its analogue (S)-α-phenylpropionic acid, and the drug (S)-ibuprofen. The three chirality elements are the configuration at Cα, the conformation at the Cα-C’ bond, and the distortion of the planar carboxylic group to a flat asymmetric tetrahedron. In all three compounds, a given (S) configuration at Cα predominantly induces (M) conformation at the Cα-C’ bond, which in turn preferentially distorts the carboxylic group to a tetrahedron with (R) configuration. Both steps of this chirality chain display high selectivities. Due to varying co-crystallization partners, in all the structures the molecules are in different environments with respect to packing and hydrogen bonding. Nevertheless, the structural pattern and the diaselectivities of the chirality chain persist. For phenylglycine, DFT (Density Functional Theory) calculations confirm the structural results. Full article
(This article belongs to the Special Issue A Symmetry Breaking in Design and Production of Enantiomeric Drugs)
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