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, p...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2021-10, Vol.23 (19), p.7423-7427
Main Authors: Chen, Yuan, Sun, Baobao, Wang, Ranran, Shi, Conghao, Cheng, Ming, Jiang, Juli, Lin, Chen, Wang, Leyong
Format: Article
Language:English
Subjects:
aqueous solutions
aromatic hydrocarbons
cysteine
dithiothreitol
oxidation
water solubility
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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-WP5. The chiral conformational transferring process between pR-WP5 and pS-WP5 can be easily and visually observed by reading the CD signal.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c02620