Regioselectivity Switches between Anthraquinone Precursor Fissions Involved in Bioactive Xanthone Biosynthesis DOI Creative Commons
Xiaojing Lv,

Chun-Zhi Ai,

Li Rong Zhang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Xanthone-based polyketides with complex molecular frameworks and potent bioactivities distribute function in different biological kingdoms, yet their biosynthesis remains under-investigated. In particular, nothing is known regarding how to switch between the C

Language: Английский

BTG13-related metalloenzymes: atypical non-heme iron-dependent dioxygenases with unusual coordination patterns and catalytic mechanisms DOI Creative Commons
Zhiwei Deng, Zhenbo Yuan, Zhengshan Luo

et al.

Engineering Microbiology, Journal Year: 2025, Volume and Issue: unknown, P. 100188 - 100188

Published: Jan. 1, 2025

Language: Английский

Citations

0
Computational Modeling of the Enzymatic Achmatowicz Rearrangement by Heme-Dependent Chloroperoxidase: Reaction Mechanism, Enantiopreference, Regioselectivity, and Substrate Specificity DOI
Fuqiang Chen, Chenghua Zhang, Shiqing Zhang

et al.

Journal of Chemical Information and Modeling, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

The chloroperoxidase from Caldariomyces fumago (CfCPO) catalyzes the oxidative ring expansion of α-heterofunctionalized furans via Achmatowicz rearrangement, providing an elegant tool to convert furan rings into complex-prefunctionalized scaffolds. However, mechanism this transformation remains unclear. Herein, CfCPO-catalyzed reaction rac-1-(2-furyl)ethanol (1a) is studied by quantum chemical calculations and molecular dynamics simulations. reveal that conversion follows general reaction. Notably, binding 1a enzyme's active site influences Compound I (Cpd I) formation, (R)-1a enantiomer results in a lower barrier compared (S)-1a, explaining observed (R)-enantiopreference toward racemic substrate. Additionally, due weaker steric hindrance between porphyrin substrate, nucleophilic attack Cpd on core preferred at less-substituted C4=C5 bond, rationale for experimentally regioselectivity. Finally, bottleneck residues substrate delivery channel also surroundings are proposed be responsible specificity CfCPO. This study lays theoretical foundation rational design new CPOs catalyze rearrangement with broader spectrum or specific stereopreference.

Language: Английский

Citations

0
A concise enzyme cascade enables the manufacture of natural and halogenated protoberberine alkaloids DOI Creative Commons
Fei Li, Zhenbo Yuan, Yue Gao

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 23, 2025

Language: Английский

Citations

0
Protein-derived cofactors: chemical innovations expanding enzyme catalysis DOI Creative Commons
Angelica Graciano, Aimin Liu

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Protein-derived cofactors, formed through posttranslational modification of a single amino acid or covalent crosslinking side chains, represent rapidly expanding class catalytic moieties that redefine enzyme functionality.

Language: Английский

Citations

0
Substrate specificity of a branch of aromatic dioxygenases determined by three distinct motifs DOI
Chengsen Cui, Lujia Yang,

Z. E. Liu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 3, 2024

Language: Английский

Citations

3
Regioselectivity Switches between Anthraquinone Precursor Fissions Involved in Bioactive Xanthone Biosynthesis DOI Creative Commons
Xiaojing Lv,

Chun-Zhi Ai,

Li Rong Zhang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Xanthone-based polyketides with complex molecular frameworks and potent bioactivities distribute function in different biological kingdoms, yet their biosynthesis remains under-investigated. In particular, nothing is known regarding how to switch between the C

Language: Английский

Citations

1