CAS 42267-27-6

N-Trifluoroacetyl-L-lysine N-carboxyanhydride

Description:

N-Trifluoroacetyl-L-lysine N-carboxyanhydride (CAS 42267-27-6) is a chemical compound that belongs to the class of N-carboxyanhydrides (NCAs), which are important intermediates in the synthesis of polypeptides and proteins. This compound features a trifluoroacetyl group, which enhances its reactivity and solubility in organic solvents. The presence of the lysine residue contributes to its potential for forming peptide bonds, making it useful in polymer chemistry and biochemistry. N-Trifluoroacetyl-L-lysine N-carboxyanhydride is typically characterized by its stability under anhydrous conditions and its ability to undergo polymerization in the presence of nucleophiles, such as amines or alcohols. Its trifluoroacetyl modification can also influence the physical properties of the resulting polymers, such as hydrophobicity and thermal stability. Overall, this compound serves as a valuable tool in the synthesis of functionalized peptides and polymers, with applications in drug delivery, biomaterials, and other fields of materials science.

Formula: C₉H₁₁F₃N₂O₄

InChI: InChI=1/C9H11F3N2O4/c10-9(11,12)7(16)13-4-2-1-3-5-6(15)18-8(17)14-5/h5H,1-4H2,(H,13,16)(H,14,17)/t5-/m0/s1

InChI key: InChIKey=KWNIHCJDDYRQFW-YFKPBYRVSA-N

SMILES: C(CCCNC(C(F)(F)F)=O)[C@H]1C(=O)OC(=O)N1

Synonyms:

• (S)-N-(4-(2,5-dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide
• Acetamide, N-[4-(2,5-dioxo-4-oxazolidinyl)butyl]-2,2,2-trifluoro-, (S)-
• Acetamide, N-[4-[(4S)-2,5-dioxo-4-oxazolidinyl]butyl]-2,2,2-trifluoro-
• H-Lys(Tfa)-Nca
• N-Trifluoroacetyl-<span class="text-smallcaps">L</span>-lysine N-carboxyanhydride
• N-[4-[(4S)-2,5-Dioxo-4-oxazolidinyl]butyl]-2,2,2-trifluoroacetamide
• N-[4-[(4S)-2,5-Dioxooxazolidin-4-Yl]Butyl]-2,2,2-Trifluoro-Acetamide
• N-{4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butyl}-2,2,2-trifluoroacetamide
• N^ε-Trifluoroacetyl-<span class="text-smallcaps">L</span>-lysine N-carboxyanhydride
• N-Trifluoroacetyl-L-lysine N-carboxyanhydride
• Nε-Trifluoroacetyl-L-lysine N-carboxyanhydride
• 4-[(4S)-2,5-DIOXOOXAZOLIDIN-4-YL]BUTYL]-2,2,2-TRIFLUORO-ACETAMIDE
• Lysine-TFA-NCA
• (S)-N-[4-(2,5-Dioxo-4-oxazolidinyl)butyl]-2,2,2-trifluoroacetaMide
• Lys-NCA
• e-Trifluoroacetyl-Lysine, NCA
• L-Lys(TFA)-NCA
• Nepsilon-Trifluoroacetyl-Nalpha-carboxy-L-lysine Anhydride
• -N-(4-(2,5-Dioxooxazolidin-4-yl)
• N6-Trifluoroacetyl-L-lysine N-Carboxyanhydride
• N-(4-(2,5-Dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide
• N-[3-[(4S)-2,5-dioxooxazolidin-4-yl]propyl]-2,2,2-trifluoro-acetaMide
• L-LYS(TFA)-NCA(42267-27-6)
• L-Lysine-N-Trifluoroacetyl-N-Carboxyanhydride
• N-trifluoroacetyl lysine N-carboxyanhydride

N-[4-[(4S)-2,5-DIOXOOXAZOLIDIN-4-YL]BUTYL]-2,2,2-TRIFLUORO-ACETAMIDE

CAS: 42267-27-6

Formula: C₉H₁₁F₃N₂O₄

Purity: 95%

Color and Shape: Solid

Molecular weight: 268.1898

Ref: IN-DA00C0SG

(S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide

CAS: 42267-27-6

(S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide

Purity: 98%

Molecular weight: 268.19g/mol

Ref: 54-PC99772

(S)-N-(4-(2,5-Dioxooxazolidin-4-yl)butyl)-2,2,2-trifluoroacetamide

CAS: 42267-27-6

Formula: C₉H₁₁F₃N₂O₄

Purity: 95%

Color and Shape: Solid

Molecular weight: 268.192

Ref: 10-F225539

N-Trifluoroacetyl-L-lysine N-Carboxyanhydride

CAS: 42267-27-6

Formula: C₉H₁₁F₃N₂O₄

Molecular weight: 268.19

Ref: 4Z-L-138044

N6-Trifluoroacetyl-L-lysine N-Carboxyanhydride

CAS: 42267-27-6

Applications Used in the synthesis of new arborescent architectures of poly(L-lysine), called lysine dendrigraft (DGL) polymers.  DGL polymers were prepd. through a multiple-generation scheme (up to generation 5) in a weakly acidic aq. medium by polycondensing N.vepsiln.-trifluoroacetyl-L-lysine-N-carboxyanhydride (Lys(Tfa)-NCA) onto the previous generation G(n-1) of DGL, which was used as a macroinitiator.
References Svenson, S., et al.: Adv. Drug Delivery Rev., 57, 2106 (2005), Shen, X., et al.: Org. Biomol. Chem., 5, 3674 (2007),

Formula: C₉H₁₁F₃N₂O₄

Color and Shape: Neat

Molecular weight: 268.19

Ref: TR-T788530

N6-Trifluoroacetyl-L-lysine N-carboxyanhydride

CAS: 42267-27-6

Trifluoroacetyl-L-lysine N-carboxyanhydride is an N6-trifluoroacetylated lysine derivative that is used in the synthesis of peptides. It is a racemic mixture of L and D forms, which is hydrolyzed to form L-glutamic acid, NH4Cl, and CO2. Trifluoroacetyl-L-lyside N-carboxyanhydride has been shown to be useful in the formation of bonds between amino acids, such as lysine and dipeptides. The compound is also used for the protection of lysine against oxidation during peptide synthesis.

Formula: C₉H₁₁F₃N₂O₄

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 268.19 g/mol

Ref: 3D-FT28454

(S)-N-[4-(2,5-Dioxooxazolidin-4-yl)butyl]-2,2,2-trifluoroacetamide

CAS: 42267-27-6

Formula: C₉H₁₁F₃N₂O₄

Purity: >98.0%(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 268.19

Ref: 3B-D5600