Recent Developments and Challenges in the Enzymatic Formation of Nitrogen–Nitrogen Bonds DOI Creative Commons

Charitomeni Angeli,

Sara Atienza-Sanz, Simon Schröder

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 310 - 342

Published: Dec. 17, 2024

The biological formation of nitrogen–nitrogen (N–N) bonds represents intriguing reactions that have attracted much attention in the past decade. This interest has led to an increasing number N–N bond-containing natural products (NPs) and related enzymes catalyze their (referred this review as NNzymes) being elucidated studied greater detail. While more detailed information on biosynthesis NPs, which only become available recent years, provides unprecedented source biosynthetic enzymes, potential for biocatalytic applications been minimally explored. With review, we aim not provide a comprehensive overview both characterized NNzymes hypothetical biocatalysts with putative bond forming activity, but also highlight from perspective. We present compare conventional synthetic approaches linear cyclic hydrazines, hydrazides, diazo- nitroso-groups, triazenes, triazoles allow comparison enzymatic routes via these functional groups. Moreover, pathways well diversity reaction mechanisms are presented according direct groups currently accessible enzymes.

Language: Английский

Elucidation of Chalkophomycin Biosynthesis Reveals N-Hydroxypyrrole-Forming Enzymes DOI Creative Commons
Anne Marie Crooke, Anika K. Chand, Zheng Cui

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(23), P. 16268 - 16280

Published: May 29, 2024

Reactive functional groups, such as N-nitrosamines, impart unique bioactivities to the natural products in which they are found. Recent work has illuminated enzymatic N-nitrosation reactions microbial product biosynthesis, motivating interest discovering additional metabolites constructed using reactivity. Here, we use a genome mining approach identify over 400 cryptic biosynthetic gene clusters (BGCs) encoding homologues of N-nitrosating enzyme SznF, including BGC for chalkophomycin, CuII-binding metabolite that contains C-type diazeniumdiolate and N-hydroxypyrrole. Characterizing chalkophomycin enzymes reveals previously unknown responsible N-hydroxypyrrole first prolyl-N-hydroxylase, key step assembly diazeniumdiolate-containing amino acid graminine. Discovery this pathway enriches our understanding logic employed constructing unusual heteroatom–heteroatom bond-containing enabling future efforts discovery biocatalysis.

Language: Английский

Citations

6
Copper-chelating natural products DOI
Olivia M. Manley, Amy C. Rosenzweig

JBIC Journal of Biological Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

Language: Английский

Citations

0
Elucidation of chalkophomycin biosynthesis revealsN-hydroxypyrrole-forming enzymes DOI Creative Commons
Anne Marie Crooke, Anika K. Chand, Zheng Cui

et al.

bioRxiv (Cold Spring Harbor Laboratory), Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 25, 2024

Reactive functional groups, such as

Language: Английский

Citations

2
Recent Developments and Challenges in the Enzymatic Formation of Nitrogen–Nitrogen Bonds DOI Creative Commons

Charitomeni Angeli,

Sara Atienza-Sanz, Simon Schröder

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 310 - 342

Published: Dec. 17, 2024

The biological formation of nitrogen–nitrogen (N–N) bonds represents intriguing reactions that have attracted much attention in the past decade. This interest has led to an increasing number N–N bond-containing natural products (NPs) and related enzymes catalyze their (referred this review as NNzymes) being elucidated studied greater detail. While more detailed information on biosynthesis NPs, which only become available recent years, provides unprecedented source biosynthetic enzymes, potential for biocatalytic applications been minimally explored. With review, we aim not provide a comprehensive overview both characterized NNzymes hypothetical biocatalysts with putative bond forming activity, but also highlight from perspective. We present compare conventional synthetic approaches linear cyclic hydrazines, hydrazides, diazo- nitroso-groups, triazenes, triazoles allow comparison enzymatic routes via these functional groups. Moreover, pathways well diversity reaction mechanisms are presented according direct groups currently accessible enzymes.

Language: Английский

Citations

1