Electrostatic Assistance of 4-Mercaptophenylacetic Acid-Catalyzed Native Chemical Ligation.
Org Lett
; 25(15): 2696-2700, 2023 Apr 21.
Article
in En
| MEDLINE
| ID: mdl-37027311
ABSTRACT
4-Mercaptophenylacetic acid (MPAA) is a popular catalyst of the native chemical ligation (NCL) but has to be used in large excess for achieving practically useful rates (up to 50-100 equiv). We report here that the catalytic potency of MPAA can be boosted by introducing a stretch of arginines in the departing thiol from the thioester. By doing so, the electrostatically assisted NCL reaction proceeds rapidly by using substoichiometric concentrations of MPAA, an advantage that enables useful synthetic applications.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2023
Document type:
Article
Affiliation country: