HTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers DOI

David A. Petrone,

Damien Valette,

Olivia Boyd

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

We report the remote stereocontrol of all-carbon quaternary γ-centers via an ene-reductase (ERED)-catalyzed desymmetrization prochiral cyclohexadienones. By leveraging high-throughput experimentation (HTE) protocols, we were able to rapidly identify EREDs capable desymmetrizing both spirocyclic cyclohexadienones and non-spirocyclic 2,6-disubstituted cyclohexadienone substrates in up 85% yield with excellent levels stereoselectivity (up >99% ee >20:1 dr) under mild reaction conditions.

Language: Английский

Biocatalytic desymmetrization for synthesis of chiral enones using flavoenzymes DOI

Qing‐Qing Zeng,

Qian-Yi Zhou, Carla Calvó‐Tusell

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(11), P. 1340 - 1348

Published: July 1, 2024

Language: Английский

Citations

4
Structure, Oligomerization, and Thermal Stability of a Recently Discovered Old Yellow Enzyme DOI Creative Commons
Nakia Polidori, Patrick J. Babin, Bastian Daniel

et al.

Proteins Structure Function and Bioinformatics, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 22, 2025

ABSTRACT The Old Yellow Enzyme from Ferrovum sp. JA12 (FOYE) displays an unusual thermal stability for enzyme isolated a mesophilic organism. We determined the crystal structure of this and performed bioinformatic characterization to get insights into its stability. tetrameric quaternary structure; however, unlike other homologs, it clusters in separate phylogenetic group possesses unique interactions that stabilize oligomeric state. is mainly due unusually high number intramolecular hydrogen bonds. Finally, study provides general analysis forces driving oligomerization Enzymes.

Language: Английский

Citations

0
New Synthetic Approaches for the Construction of Enantioenriched Molecules Bearing Quaternary Stereocenters DOI
Zhou Sun, Jiaxuan Liu, Lin Shi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4294 - 4322

Published: Aug. 17, 2024

Abstract Optically active molecule architectures stand as an important class of organic compounds and occupy a key role in academic industrial communities. Particularly, the molecules bearing quaternary carbon are vital importance because its favorable conformation valuable three‐dimensional molecules, which frequently play broad spectrum functional materials, pharmaceutical relevant natural agrochemicals. Over past few decades, large number synthetic strategies for enantioselective construction with chiral centers have been focus research initiatives. In this review, state‐of‐the‐art toward synthesis enantioenriched stereocenters summarized, could be segmented into four categories: 1) Construction optically by addition to prochiral sp 2 carbon; 2) all‐carbon via substitution at non‐chiral tetra‐substituted 3) kinetic resolution; 4) desymmetrization reactions.

Language: Английский

Citations

2
HTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers DOI

David A. Petrone,

Damien Valette,

Olivia Boyd

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

We report the remote stereocontrol of all-carbon quaternary γ-centers via an ene-reductase (ERED)-catalyzed desymmetrization prochiral cyclohexadienones. By leveraging high-throughput experimentation (HTE) protocols, we were able to rapidly identify EREDs capable desymmetrizing both spirocyclic cyclohexadienones and non-spirocyclic 2,6-disubstituted cyclohexadienone substrates in up 85% yield with excellent levels stereoselectivity (up >99% ee >20:1 dr) under mild reaction conditions.

Language: Английский

Citations

0