(2S)-2-amino-6-(trifluoroacetamido)hexanoic acid

• ChemBase ID: 94308
• Molecular Formular: C8H13F3N2O3
• Molecular Mass: 242.1956296
• Monoisotopic Mass: 242.08782695
• SMILES: N(C(=O)C(F)(F)F)CCCC[C@@H](C(=O)O)N
• Canonical SMILES: OC(=O)[C@H](CCCCNC(=O)C(F)(F)F)N
• InChI: InChI=1S/C8H13F3N2O3/c9-8(10,11)7(16)13-4-2-1-3-5(12)6(14)15/h5H,1-4,12H2,(H,13,16)(H,14,15)/t5-/m0/s1
• InChIKey: PZZHRSVBHRVIMI-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-(trifluoroacetamido)hexanoic acid
• IUPAC Traditional name: (2S)-2-amino-6-(trifluoroacetamido)hexanoic acid; N6-(trifluoroacetyl)-L-lysine
• Synonyms: H-Lys(Tfa)-OH; N6-Trifluoroacetyl-L-lysine 98%; ε-TFA-lysine; Nε-Trifluoroacetyl-L-lysine; N6-(2,2,2-Trifluoroacetyl)-L-lysine; N6-(Trifluoroacetyl)lysine; Nε-Trifluoroacetyl-L-lysine; Nω-(Trifluoroacetyl)-L-lysine; N6-Trifluoroacetyl-L-lysine

Database IDs

• CAS Number: 10009-20-8
• MDL Number: MFCD00037223
• Beilstein Number: 2122429
• PubChem SID: 24878129; 162080962
• PubChem CID: 7009573

CALCULATED PROPERTIES

• Acid pKa: 2.0008624
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.0956748
• LogD (pH = 7.4): -2.8117821
• Log P: -2.0271525
• Molar Refractivity: 48.2635 cm^3
• Polarizability: 18.425383 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 2 M HCl: soluble10 mg/mL, clear, colorless; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 247-249°C; 258°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Irritant
• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (TLC); 95+%
• Impurities: ≤7% water
• Empirical Formula (Hill Notation): C8H13F3N2O3

DETAILS

Sigma Aldrich - 53604

Biochem/physiol Actions
Nε-Trifluoroacetyl-L-lysine is an inhibitor of L-lysine cyclodeaminase.
Nε-Trifluoroacetyl-L-lysine may be used to create synthetic organic polypeptides useful for nonaqueous capillary electrophoresis (NACE).

Toronto Research Chemicals - T788500

A cysteine conjugate metabolite adduct formation with specific mitochondrial proteins using antibodies raised against halothane metabolite adducts.

REFERENCES

• Hayden, P.J., et al.: J. Biol. Chem., 266, 18415 (1991)