O-Phosphono-L-homoserine
O-Phosphono-L-homoserine (o-Phosphohomoserine) is an intermediate in threonine synthesis in bacteria and plants, and can also be hijacked by MetM in some Streptomyces species to enter a novel methionine synthesis pathway. O-Phosphono-L-homoserine acts as a weak antagonist of the NMDA receptor. O-Phosphono-L-homoserine can be used as a substrate for studies on amino acid metabolism of the aspartate family, a control for mechanism studies of PLP enzymes, and a reference for structure-activity relationship studies of NMDA receptor ligands.
For research use only. We do not sell to patients.
- CAS No.: 4210-66-6
- Formula: C4H10NO6P
- Molecular Weight:199.10
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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NMDA Receptor |
O-Phosphono-L-homoserine (100 μM; 1 h) can be converted to L-Homocysteine (HY-W010347) by MetM from Streptomyces albus using 100 μM Na2S or 100 μM Na2S2 as the inorganic sulfur donor[1].
O-Phosphono-L-homoserine (0.5-1 mM) acts as a weak, selective NMDA receptor antagonist in rat hippocampal CA1 brain slices, exhibiting significant activity at concentrations of 0.5 mM and 1 mM, with no effect on responses to Kainic acid (HY-N2309) or Quisqualic acid (HY-12597) at these concentrations[2].
O-Phosphono-L-homoserine (0-30 min) is not metabolized by rat brain crude homogenate or bovine liver alkaline phosphatase after incubation at 37°C for up to 30 min[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 4210-66-6
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Molecular Weight 199.10
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Formula C4H10NO6P
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SMILES
N[C@@H](CCOP(O)(O)=O)C(O)=O
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Synonyms
o-Phosphohomoserine
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Hasebe F, et al. Discovery of a novel methionine biosynthetic route via O-phospho-l-homoserine. Appl Environ Microbiol. 2024;90(10):e0124724. [Content Brief]
[2]. Connick JH, et al. O-phosphohomoserine, a naturally occurring analogue of phosphonate amino acid antagonists, is an N-methyl-D-aspartate (NMDA) antagonist in rat hippocampus. Neurosci Lett. 1986;68(2):249-251. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
O-Phosphono-L-homoserine Related Classifications
HY-W051199 Related Classifications
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- O-Phosphono-L-homoserine
- 4210-66-6
- o-Phosphohomoserine
- Endogenous Metabolite
- iGluR
- N-methyl-D-aspartate (NMDA) receptor
- methionine biosynthesis
- L-homocysteine
- threonine biosynthesis
- bovine liver alkaline phosphatase
- MetM/MetO pathway
- Streptomyces
- rat hippocampal CA1 slices
- rat brain homogenates
- Streptomyces albulus
- Inhibitor
- inhibitor
- inhibit