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 inOrganic letters Vol. 23; no. 19; pp. 7423 - 7427
Main Authors Chen, Yuan, Sun, Baobao, Wang, Ranran, Shi, Conghao, Cheng, Ming, Jiang, Juli, Lin, Chen, Wang, Leyong
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.10.2021
Subjects
aqueous solutions
aromatic hydrocarbons
cysteine
dithiothreitol
oxidation
water solubility
Online AccessGet full text

Cover

More Information
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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c02620