Synonym
TrifluoroacetylLysine, TfAcK, Lys(TFA)-OH
IUPAC/Chemical Name
N6-(Trifluoroacetyl)-L-lysine; (2S)-2-Amino-6-[(2,2,2-trifluoroacetyl)amino]hexanoic acid
InChi Key
PZZHRSVBHRVIMI-YFKPBYRVSA-N
InChi Code
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
SMILES Code
FC(F)(F)C(NCCCC[C@H](N)C(O)=O)=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
242.20
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Patel KD, Mohid SA, Dutta A, Arichthota S, Bhunia A, Haldar D, Sarojini V. Synthesis and antibacterial study of cell-penetrating peptide conjugated trifluoroacetyl and thioacetyl lysine modified peptides. Eur J Med Chem. 2021 Jul 5;219:113447. doi: 10.1016/j.ejmech.2021.113447. Epub 2021 Apr 20. PMID: 33892275.
2: Miller GM, Flynn EM, Tom J, Song A, Cochran AG. Trifluoroacetyl Lysine as a Bromodomain Binding Mimic of Lysine Acetylation. ACS Chem Biol. 2022 May 20;17(5):1022-1029. doi: 10.1021/acschembio.2c00016. Epub 2022 Apr 25. PMID: 35467836.
3: Rodríguez-Hernández J, Gatti M, Klok HA. Highly branched poly(L-lysine). Biomacromolecules. 2003 Mar-Apr;4(2):249-58. doi: 10.1021/bm020096k. PMID: 12625719.
4: Forget SM, Robertson AW, Overy DP, Kerr RG, Jakeman DL. Furan and Lactam Jadomycin Biosynthetic Congeners Isolated from Streptomyces venezuelae ISP5230 Cultured with Nε-Trifluoroacetyl-l-lysine. J Nat Prod. 2017 Jun 23;80(6):1860-1866. doi: 10.1021/acs.jnatprod.7b00152. Epub 2017 May 18. PMID: 28520425.
5: Smith BC, Denu JM. Mechanism-based inhibition of Sir2 deacetylases by thioacetyl-lysine peptide. Biochemistry. 2007 Dec 18;46(50):14478-86. doi: 10.1021/bi7013294. Epub 2007 Nov 21. PMID: 18027980.
6: Hughes RM, Waters ML. Effects of lysine acetylation in a beta-hairpin peptide: comparison of an amide-pi and a cation-pi interaction. J Am Chem Soc. 2006 Oct 18;128(41):13586-91. doi: 10.1021/ja0648460. PMID: 17031973.
7: Tsotsou GE, Barbirato F. Biochemical characterisation of recombinant Streptomyces pristinaespiralis L-lysine cyclodeaminase. Biochimie. 2007 May;89(5):591-604. doi: 10.1016/j.biochi.2006.12.008. Epub 2007 Jan 8. PMID: 17291665.
8: Vayaboury W, Giani O, Collet H, Commeyras A, Schué F. Synthesis of Nepsilon- protected-L-lysine and gamma-benzyl-L-glutamate N-carboxyanhydrides (NCA) by carbamoylation and nitrosation. Amino Acids. 2004 Oct;27(2):161-7. doi: 10.1007/s00726-004-0112-6. Epub 2004 Sep 22. PMID: 15378412.
9: Collet H, Souaid E, Cottet H, Deratani A, Boiteau L, Dessalces G, Rossi JC, Commeyras A, Pascal R. An expeditious multigram-scale synthesis of lysine dendrigraft (DGL) polymers by aqueous N-carboxyanhydride polycondensation. Chemistry. 2010 Feb 15;16(7):2309-16. doi: 10.1002/chem.200901734. PMID: 20033966.
10: Ahmed AJ, Millett F. Use of specific lysine modifications to identify the site of reaction between cytochrome c and ferricyanide. J Biol Chem. 1981 Feb 25;256(4):1611-5. PMID: 6257681.
