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Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods
Published on: October 6, 2023
Biosynthesis of 2-hydroxyethylphosphonate, an unexpected intermediate common to multiple phosphonate biosynthetic
Zengyi Shao1, Joshua A V Blodgett, Benjamin T Circello
1Department of Chemical and Biomolecular Engineering and Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
The Journal of Biological Chemistry
|June 12, 2008
Summary
Researchers discovered a common intermediate, 2-hydroxyethyl-phosphonate, in the biosynthesis of diverse phosphonic acids. This finding reveals a shared enzymatic step involving unique alcohol dehydrogenases (ADHs) in natural product synthesis.
Area of Science:
- Biochemistry
- Natural Product Synthesis
- Enzymology
Background:
- Phosphonic acids are a diverse class of natural products with significant biological activities.
- Their biosynthetic pathways are varied, making a common synthetic step unexpected.
Purpose of the Study:
- To identify common intermediates and enzymatic steps in the biosynthesis of diverse phosphonic acids.
- To characterize the alcohol dehydrogenases (ADHs) involved in these pathways.
Main Methods:
- In vitro biochemical characterization of ADH homologs.
- Sequence analysis of ADH family members.
- Investigation of phosphonate biosynthetic gene clusters.
Main Results:
- Identified 2-hydroxyethyl-phosphonate as a common intermediate.
- Demonstrated that distinct, metal-dependent ADHs catalyze its synthesis from phosphonoacetaldehyde.
- Characterized these ADHs for substrate specificity, metal requirements, and monomeric structure.
- Showed these ADHs form a monophyletic group within a larger family.
Conclusions:
- The reduction of phosphonoacetaldehyde to 2-hydroxyethyl-phosphonate is likely a common step in phosphonate natural product biosynthesis.
- This finding provides insight into the evolution of C-P bond-containing natural product pathways.
- Suggests potential for discovering new phosphonate natural products.
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