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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
Very potent blocker for the human excitatory amino acid transporters (EAAT1–3; IC50 values 23 µM, 3.8 µM, 7.0 µM for EAAT1, EAAT2, and EAAT3, respectively). L-TBOA is the most active isomer of DL-TBOA, as sold by competitors, and approximately twice as potent for inhibition of EAAT1 and EAAT2.
| EAAT1 | EAAT2 | EAAT3 | ||
| (IC50 μM) | (IC50 μM) | (IC50 μM) | ||
| dl-TBOA | 48 ± 4.1 | 7.0 ± 1.1 | 8.0 ± 1.9 | |
| l-TBOA | 23 ± 4.4 | 3.8 ± 1.0 | 7.0 ± 1.5 | |
| d-TBOA | 637 ± 175 | 64 ± 14 | 21 ± 2.3 |
IC50 values of THA derivatives for blocking [14C]glutamate uptake in COS-1 cells expressing EAAT1–3 (data taken from Shimamoto et al.)
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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