Figure 1
From: Enantiomer-specific activities of an LRH-1 and SF-1 dual agonist
RJW100 enantiomers. (a) Chemical structures of SS- and RR-RJW100. (b) HPLC traces for RR-RJW100 generated by enantioselective synthesis (black curve) and for the racemate (blue curve). Separation by HPLC resulted in enantiopure RR-RJW100 and SS-RJW100 (both 100% ee). (c) Enantioselective synthesis of RR-RJW100. The (R)-enantiomer of the alcohol 1 was obtained from the racemate by kinetic resolution using a crotylation reaction with Novozyme 435, an immobilized Candida antartica lipase as the catalyst, which is known to be selective for the (S)-enantiomer of alcohols with a similar structure54. The reaction was stopped at around 50% conversion. The recovered enantioenriched alcohol (R)-1 (95:5 enantiomer ratio) protected as the tert-butyldimethylsilyl ether and converted to RR-RJW100 (95:5 enantiomer ratio) using the published procedure for the racemate33,34. The enantio-enriched RR-RJW100 was used to identify the two HPLC peaks from the racemate and was not used for experiments with LRH-1/ SF-1. (d) CD traces of the RJW100 enantiomers used in these studies.
