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L-TBOA ammonia salt
- TBOA - (3S)-3-(Phenylmethoxy)-L-aspartic acid ammonia salt
- Parent CAS: 208706-75-6
- Optical Purity: Optically pure
- Soluble in water and DMSO
- MF: C11H13NO5.NH3
- MW: 256.26
Description
L-TBOA ammonia salt is a potent blocker of excitatory amino acid transporters EAAT1, EAAT2 and EAAT3. It inhibits glutamate uptake and is used to increase extracellular glutamate signaling in transporter-dependent experimental systems. L-TBOA is the active stereoisomer of DL-TBOA and delivers roughly twice the inhibitory potency against EAAT1 and EAAT2 relative to the racemic mixtures sold by some competitors.
EAAT transporters regulate synaptic glutamate clearance, excitotoxicity and astrocyte-neuron communication. L-TBOA ammonia salt is a key tool for studying glutamate transporter pharmacology, transporter currents and excitatory neurotransmission.
Key Features
- Broad EAAT1-3 glutamate transporter blocker
- Reported IC50 values: 23 µM for EAAT1, 3.8 µM for EAAT2 and 7.0 µM for EAAT3
- Active L-isomer of TBOA
- Inhibits glutamate uptake in transporter-expressing systems
Applications
- Glutamate transporter pharmacology
- Excitatory neurotransmission studies
- Astrocyte-neuron signaling research
- Excitotoxicity and synaptic clearance assays
More Information
| Parent CAS No. | 208706-75-6 |
|---|---|
| Chemical Name | (2S,3S)-2-amino-3-(benzyloxy)succinic acid, ammonia salt |
| SMILES | C(O)(=O)[C@H]([C@H](OCC1=CC=CC=C1)C(O)=O)N.N |&1:3,4,r| |
| MFCD | N.A. |
| InChi | InChI=1S/C11H13NO5.H3N/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7;/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16);1H3/t8-,9-;/m0./s1 |
| InChiKey | NWSNCKZFVJQJRK-OZZZDHQUSA-N |
| CID | 91900718 |
| Short Description | EAAT blocker |
References
- K. Shimamoto et al. Syntheses of optically pure beta-hydroxyaspartate derivatives as glutamate transporter blockers. Bioorg Med Chem Lett. 2000 Nov 6;10(21):2407-10.
- H. Raj et al. Engineering methylaspartate ammonia lyase for the asymmetric synthesis of unnatural amino acids. Nat Chem. 2012 Apr 29;4(6):478-84.
- J. de Villiers et al. Chemoenzymatic Synthesis of ortho-, meta-, and para-Substituted Derivatives of l-threo-3-Benzyloxyaspartate, An Important Glutamate Transporter Blocker. ChemCatChem. 2015 Jul 3;7(13):1931-1934.
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