Nov 20, 2018 · We hypothesize that a fraction of thalidomide enantiomers epimerizes in vivo, followed by precipitation of racemic thalidomide in (R/S)-heterodimeric form.

Thalidomide is provided as a racemic mixture of two enantiomers; while there are reports that only one of the enantiomers may cause birth defects, the body converts each enantiomer into the other through mechanisms that are not well understood. [22]

Thalidomide has a chiral carbon, which is unstable and allows two enantiomers to coexist, which can interswitch between the two states rapidly in bodily fluids and in water (Smith et al., 1965; Franks et al., 2004). One of the enantiomers is teratogenic, the S‐enantiomer.

May 17, 2010 · The thalidomide disaster caused many countries to tighten drug approval regulations. Thalidomide exists in two mirror-image forms: it is a racemic mixture of ( R )- and ( S )-enantiomers. The ( R )-enantiomer, shown in the figure, has sedative effects, whereas the ( S )-isomer is teratogenic.

Thalidomide is a racemic glutamic acid analog with interchanging S(-) and R(+) enantiomers. The S(-) enantiomer directly inhibits the release of TNF-alpha, while the R(+) enantiomer acts as a sedative via sleep receptors.

Thalidomide is composed of two parts: a phthalimide ring and a glutarimide ring. We synthesized thalidomide derivative FR259625, which has a carboxylic acid group, and covalently attached it through this group to amino groups on FG beads (Fig. 2B).

Jan 22, 2018 · Our biochemical studies employed deuterium-substituted thalidomides to suppress optical isomer conversion, and established that the (S)-enantiomer exhibited ~10-fold stronger binding to CRBN and...

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...

The aim of this investigation was to elucidate the distribution and reactions of the enantiomers of thalidomide at their main site of biotransformation in vivo, i.e., in human blood. Plasma protein binding, erythrocyte: plasma distribution, and the kinetics of chiral inversion and degradation in buf …

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 / …