Epoxide Ring-Opening Reactions for Abundant Production of Mugineic Acids and Nicotianamine Probes.
Angew Chem Int Ed Engl
; 63(20): e202401411, 2024 05 13.
Article
in En
| MEDLINE
| ID: mdl-38500479
ABSTRACT
A succinct synthetic approach to mugineic acids and 2'-hydroxynicotianamine was established. Unlike all other synthetic methods, this approach utilized epoxide ring-opening reactions to form two C-N bonds and is characterized by the absence of redox reactions. Mugineic acid was synthesized from three readily available fragments on a gram scale in 6 steps. The protected 2'-hydroxynicotianamine was also synthesized in 4 steps, and the dansyl group, serving as a fluorophore, was introduced through a click reaction after propargylation of the 2'-hydroxy group. The dansyl-labeled nicotianamine (NA) iron complexes were internalized by oocytes overexpressing ZmYS1 (from maize) or PAT1 (from human) transporters, indicating successful transport of the synthesized NA-probe through these transporters.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Azetidinecarboxylic Acid
/
Epoxy Compounds
Limits:
Humans
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2024
Document type:
Article
Affiliation country:
Country of publication: