8AUB

12-oxophytodienoate reductase 3 (OPR3) from Solanum lycopersicum in complex with ethyl (Z)-2-(hydroxyimino)-3-oxopentanoate

8AUB の概要

• エントリーDOI: 10.2210/pdb8aub/pdb
• 分子名称: 12-oxophytodienoate reductase 3, FLAVIN MONONUCLEOTIDE, ethyl (2~{Z})-2-hydroxyimino-3-oxidanylidene-pentanoate, ... (5 entities in total)
• 機能のキーワード: ene-reductase, oxime, fmn, complex, oxidoreductase
• 由来する生物種: Solanum lycopersicum (tomato)
• タンパク質・核酸の鎖数: 2
• 化学式量合計: 90592.03

構造登録者

Polidori, N.,Gruber, K. (登録日: 2022-08-25, 公開日: 2023-03-01, 最終更新日: 2024-02-07)

主引用文献

Breukelaar, W.B.,Polidori, N.,Singh, A.,Daniel, B.,Glueck, S.M.,Gruber, K.,Kroutil, W.
Mechanistic Insights into the Ene-Reductase-Catalyzed Promiscuous Reduction of Oximes to Amines.
Acs Catalysis, 13:2610-2618, 2023

PubMed Abstract: The biocatalytic reduction of the oxime moiety to the corresponding amine group has only recently been found to be a promiscuous activity of ene-reductases transforming α-oximo β-keto esters. However, the reaction pathway of this two-step reduction remained elusive. By studying the crystal structures of enzyme oxime complexes, analyzing molecular dynamics simulations, and investigating biocatalytic cascades and possible intermediates, we obtained evidence that the reaction proceeds an imine intermediate and not the hydroxylamine intermediate. The imine is reduced further by the ene-reductase to the amine product. Remarkably, a non-canonical tyrosine residue was found to contribute to the catalytic activity of the ene-reductase OPR3, protonating the hydroxyl group of the oxime in the first reduction step.

PubMed: 36846821
DOI: 10.1021/acscatal.2c06137

実験手法

X-RAY DIFFRACTION (1.62 Å)