(2S,3S)-2-amino-3-benzylbutanedioic acid amine

• ChemBase ID: 153976
• Molecular Formular: C11H16N2O4
• Molecular Mass: 240.25574
• Monoisotopic Mass: 240.111007
• SMILES: c1ccc(cc1)C[C@@H]([C@@H](C(=O)O)N)C(=O)O.N
• Canonical SMILES: N[C@@H]([C@@H](C(=O)O)Cc1ccccc1)C(=O)O.N
• InChI: InChI=1S/C11H13NO4.H3N/c12-9(11(15)16)8(10(13)14)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: ZFFMTFAAICLZOY-OZZZDHQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-amino-3-benzylbutanedioic acid amine
• IUPAC Traditional name: (2S,3S)-2-amino-3-benzylbutanedioic acid amine
• Synonyms: (2S,3S)-2-Amino-3-benzylsuccinic acid; DL-TBOA; (2S,3S)-2-Amino-3-benzylsuccinic ammonium salt; L-β-threo-benzyl-aspartate ammonium salt; L-β-threo-benzyl-aspartate

Database IDs

• CAS Number: 871123-98-7(freeacid)
• PubChem SID: 162248115
• PubChem CID: 71311770

CALCULATED PROPERTIES

• Acid pKa: 2.0980444
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.7311063
• LogD (pH = 7.4): -3.382285
• Log P: -1.3836675
• Molar Refractivity: 55.8032 cm^3
• Polarizability: 22.134823 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H13NO4 · xNH3

DETAILS

Sigma Aldrich - B6436

Biochem/physiol Actions
L-β-threo-benzyl-aspartate is a preferential EAAT3 excitatory amino acid transporter antagonist. The product exhibits 10-fold selectivity for EAAT3, Ki = 0.8 μM for EAAT3 in C17.2 neuroprogenitor cells expressing hEAATs (vs. Ki of 8.7 μM for EAAT1 and Ki of 10 μM for EAAT2). L-β-threo-benzyl-aspartate is a useful tool for studying the EAAT2 pharmacophore.