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
Strategic enzymatic enantioselective desymmetrization of prochiral cyclohexa-2,5-dienones DOI
Bhavita Kattula, Anandarao Munakala, R. P. KASHYAP

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(52), P. 6647 - 6650

Published: Jan. 1, 2024

Asymmetric desymmetrization through the selective reduction of one double bond prochiral 2,5-cyclohexadienones is highly challenging.

Language: Английский

Citations

1
Diversification of 3’‐Amino Nucleosides via Enzymatic Transglycosylation DOI
Li Zhang, Haiyan Xu,

Xiaofan Wu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

Abstract A systematic study on the enzymatic transglycosylation of 3′‐amino nucleosides has been reported. Using commercially available 3′‐amino‐3′‐deoxythymidine as sugar donor, 13 pyrimidine and purine nucleobases were shown viable acceptors in nucleoside phosphorylase Ec PPNP‐ and/or 2′‐deoxyribosyltransferase Ll NDT‐catalyzed reactions, furnishing corresponding containing 23%–73% NMR yields at an analytical scale. The synthetic utility this diversification approach was further showcased by successful synthesis 3′‐amino‐2′,3′‐dideoxy‐5‐bromouridine 29% isolated yield a preparative current work demonstrates activity PPNP for first time, expands substrate scope NDT, provides efficient, direct access to various high value.

Language: Английский

Citations

0
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