Phosphonate biochemistry

GP Horsman, DL Zechel - Chemical reviews, 2017 - ACS Publications
Organophosphonic acids are unique as natural products in terms of stability and mimicry.
The C–P bond that defines these compounds resists hydrolytic cleavage, while the …

Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation

X Huang, JT Groves - JBIC Journal of Biological Inorganic Chemistry, 2017 - Springer
Since our initial report in 1976, the oxygen rebound mechanism has become the consensus
mechanistic feature for an expanding variety of enzymatic C–H functionalization reactions …

Dioxygen activation by nonheme iron enzymes with the 2-His-1-carboxylate facial triad that generate high-valent oxoiron oxidants

S Kal, L Que - JBIC Journal of Biological Inorganic Chemistry, 2017 - Springer
Abstract The 2-His-1-carboxylate facial triad is a widely used scaffold to bind the iron center
in mononuclear nonheme iron enzymes for activating dioxygen in a variety of oxidative …

Unusual dioxygen-dependent reactions catalyzed by nonheme iron enzymes in natural product biosynthesis

R Ushimaru, I Abe - ACS Catalysis, 2022 - ACS Publications
Nonheme iron-dependent enzymatic reactions play crucial roles in building and modifying
bioactive organic molecules in all major classes of natural product pathways. While the …

Enzymatic chemistry of cyclopropane, epoxide, and aziridine biosynthesis

CJ Thibodeaux, W Chang, H Liu - Chemical reviews, 2012 - ACS Publications
Cyclopropane, epoxide, and aziridine groups are three-membered ring structural elements
found in a wide variety of natural products, some of which are depicted in Figure 1. 1 The …

Engineering non-haem iron enzymes for enantioselective C(sp3)–F bond formation via radical fluorine transfer

Q Zhao, Z Chen, J Soler, X Chen, J Rui, NT Ji, QE Yu… - Nature …, 2024 - nature.com
In recent years there has been a surge in the development of methods for the synthesis of
organofluorine compounds. However, enzymatic methods for C–F bond formation have …

Structural and computational insights into the noncanonical aromatization in fungal polyketide biosynthesis

H Wang, C Peng, XX Chen, HY Wang, R Yang… - ACS …, 2024 - ACS Publications
Aromatic polyketides, with their diverse structures and biological activities, have attracted
significant scientific interest. Aromatization reactions are typically performed by aromatases …

Oxidative aliphatic carbon–carbon bond cleavage reactions

CJ Allpress, LM Berreau - Coordination Chemistry Reviews, 2013 - Elsevier
Over the past decade, several metalloenzymes have been characterized which catalyze
dioxygenase-type aliphatic carbon–carbon bond cleavage reactions. The substrates for …

Evidence that the fosfomycin-producing epoxidase, HppE, is a non–heme-iron peroxidase

C Wang, W Chang, Y Guo, H Huang, SC Peck… - Science, 2013 - science.org
The iron-dependent epoxidase HppE converts (S)-2-hydroxypropyl-1-phosphonate (S-HPP)
to the antibiotic fosfomycin [(1 R, 2 S)-epoxypropylphosphonate] in an unusual 1, 3 …

A new microbial pathway for organophosphonate degradation catalyzed by two previously misannotated non-heme-iron oxygenases

LJ Rajakovich, ME Pandelia, AJ Mitchell, W Chang… - Biochemistry, 2019 - ACS Publications
The assignment of biochemical functions to hypothetical proteins is challenged by functional
diversification within many protein structural superfamilies. This diversification, which is …