Chemical Properties
Off-White Solid
Uses
A cysteine conjugate metabolite adduct formation with specific mitochondrial proteins using antibodies raised against halothane metabolite adducts.
Definition
ChEBI: An N6-acyl-L-lysine where the N6-acyl group is trifluoroacetyl.
Biological Activity
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).
Synthesis
1. Sodium ethanolate solution was prepared by dissolving sodium metal (4.6 g, 0.2 mol) in 200 mL of anhydrous ethanol.
2. L-lysine hydrochloride (18.25 g, 0.1 mol) was slowly added to the above solution under stirring conditions.
3. The reaction mixture was stirred continuously for 1 hour, followed by filtration to remove the insoluble precipitate.
4. The filtrate was cooled in an ice bath and ethyl trifluoroacetate (21.3 g, 0.15 mol) was added slowly and dropwise with vigorous stirring.
5. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours.
6. Acetic acid (6 g, 0.1 mol) was added to neutralize the reaction system and the resulting precipitate was subsequently collected by filtration.
7. The precipitate was washed sequentially with ethanol and acetone and dried to give the target product trifluoroacetyl lysine.
8. Yield: 15 g (62% yield).
9. MALDI-TOF mass spectrometry (positive ion mode): m/z 242.455 ([M+H]+, relative abundance 67%).
References
[1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 10, p. 1427 - 1431
[2] Patent: WO2009/114809, 2009, A1. Location in patent: Page/Page column 7
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 255 - 258
