ArticleScientific reports2018
Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers.
Article in Scientific reports, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.
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43 citing papers in PubMed, 144 citations in OpenAlex.
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- Rapid Vibrational Circular Dichroism Spectroscopy via Synchronized Photoelastic Modulator-Quantum Cascade Laser Integration.ACS measurement science au · 2025Article
- Determination of Enantiomeric Excess in Confined Aprotic Solvent.ACS electrochemistry · 2025Article
- Imaging and spatially resolved mass spectrometry applications in nephrology.Nature reviews. Nephrology · 2025Review
- New insight into teratogenic effects of (S)-thalidomide in zebrafish embryos growing inside the chorion and subjected to electric pulses.Scientific reports · 2025Article
- Thalidomide-induced limb malformations: an update and reevaluation.Archives of toxicology · 2025Review
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- Ni-Catalyzed Asymmetric Reductive Arylation of α-Substituted Imides.Journal of the American Chemical Society · 2024Article
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- Variation of Activation Volume as an Indicator of the Difference in Clusterization Phenomenon Induced by H-Bonding and F-Π Stacking Interactions in Enantiomers and a Racemate of Flurbiprofen.The journal of physical chemistry. B · 2024Article
- Anhydrous and Stereoretentive Fluoride-Enhanced Suzuki-Miyaura Coupling of Immunomodulatory Imide Drug Derivatives.The Journal of organic chemistry · 2024Article
- Molecular glue degrader for tumor treatment.Frontiers in oncology · 2024Review
- Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Twenty years after the thalidomide disaster in the late 1950s, Blaschke et al. reported that only the (S)-enantiomer of thalidomide is teratogenic. However, other work has shown that the enantiomers of thalidomide interconvert in vivo, which begs the question: why is teratogen activity not observed in animal experiments that use (R)-thalidomide given the ready in vivo racemization ("thalidomide paradox")? Herein, we disclose a hypothesis to explain this "thalidomide paradox" through the in-vivo self-disproportionation of enantiomers. Upon stirring a 20% ee solution of thalidomide in a given solvent, significant enantiomeric enrichment of up to 98% ee was observed reproducibly in solution. We hypothesize that a fraction of thalidomide enantiomers epimerizes in vivo, followed by precipitation of racemic thalidomide in (R/S)-heterodimeric form. Thus, racemic thalidomide is most likely removed from biological processes upon racemic precipitation in (R/S)-heterodimeric form. On the other hand, enantiomerically pure thalidomide remains in solution, affording the observed biological experimental results: the (S)-enantiomer is teratogenic, while the (R)-enantiomer is not.
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