Chiral Pyridoxamines Featuring Proton-Donating Auxiliary Side Chains for Asymmetric Biomimetic Transamination
Abstract
Inspired by transaminases, we developed a novel class of chiral pyridoxamine featuring an auxiliary proton-donating side chain. These catalysts exhibited excellent activity and enantioselectivity in the asymmetric transamination of α-keto acids, affording various chiral α-amino acids in up to 97% yield with 93% ee. The strategic introduction of the auxiliary proton-donating side chain likely promotes the protonation of delocalized azaallylanion in the 1,3-proton transfer, leading to improvement in both catalytic activity and enantioselectivity.
Fields of Study & Subjects
Enzyme Structure and Function
Carbohydrate Chemistry and Synthesis
Synthesis and Catalytic Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 10
- Pages
- 3276–3280
- Publication date
- 27 February 2026
- Language
- EN