Redox-Driven Chiral Inversion of Water-Soluble Pillar[5]arene with L-Cystine Derivative in the Aqueous Medium

In the aqueous solution, L-CySS-OMe induced pS-WP5 from racemic WP5. Upon the addition of dithiothreitol as a reducing reagent to the above system, pS-WP5 was then converted to pR-WP5 for the reason that L-CySS-OMe was reduced to L-Cys-OMe. Followed by the addition of H2O2 as an oxidation reagent, pR-WP5 was converted back to pS-WPS. The chiral conformational transferring process between pR-WP5 and pS-WP5 can be easily and visually observed by reading the CD signal.

Automated summary

In an aqueous solution, L-CySS-OMe induced pS-WP5 from racemic WP5. By adding different reducing and oxidizing reagents, the chiral conformational transferring process between pR-WP5 and pS-WP5 was observed, which can be visually observed through CD signal.