N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine is a protected lysine derivative bearing an N-α Fmoc (fluorenylmethoxycarbonyl) group and an N-ε tritfluoroacetyl (trifluoroacetyl) group on the side-chain amino functionality, classifying it as an amino acid building block for peptide chemistry. The molecule contains a free carboxyl group and a side-chain carbon skeleton characteristic of lysine, with the α-amino nitrogen substituted by Fmoc and the ε-amino nitrogen acylated by the trifluoroacetyl group, while the L stereochemical designation is specified in the name. In synthesis, the orthogonally protected amines support stepwise peptide assembly by controlling chemoselectivity during coupling and deprotection, and the presence of the electron-withdrawing trifluoroacetyl group provides a protected handle for generating defined lysine-containing peptide intermediates.
CAT No: CP01448
CAS No:76265-69-5
Synonyms/Alias:Fmoc-Lys(Tfa)-OH;76265-69-5;Fmoc-N-epsilon-trifluoroacetyl-L-lysine;Nalpha-Fmoc-Nepsilon-trifluoroacetyl-L-lysine;AC1Q71CY;AC1Q71CZ;47536_ALDRICH;SCHEMBL178772;47536_FLUKA;C23H23F3N2O5;MolPort-003-934-156;CF-483;MFCD00153360;ZINC34781584;AKOS015909869;N|A-Fmoc-N|A-trifluoroacetyl-L-lysine;AJ-90172;AK-44091;K305;AB0014154;FT-0081956;FT-0651238;ST24047291;ST51054885;M-1005
N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine is an L-lysine derivative bearing an Fmoc-protected α-amino group and a trifl uoroacetyl-protected ε-amino side chain, providing two orthogonal nitrogen protecting elements for stepwise peptide assembly. The molecule contains a free carboxylic acid suitable for amide bond formation after activation, while the ε-trifluoroacetamide reduces side-chain nucleophilicity and supports controlled lysine chemistry. The stereogenic α-carbon is retained in the L-configuration, aligning with standard amino acid coupling stereochemical outcomes. The combination of Fmoc and trifl uoroacetyl protection establishes predictable deprotection and functional-group reactivity patterns that make the compound a practical chiral intermediate for protected lysine building blocks and downstream derivatization.
1. Peptide Synthesis
N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine serves as a lysine peptide building block for solid-phase peptide synthesis and solution-phase coupling workflows where orthogonal N-protection is required. The Fmoc group enables base-mediated removal to expose the α-amino function for sequential chain elongation, while the ε-trifluoroacetyl amide suppresses undesired side-chain coupling during lysine incorporation. The free carboxylic acid participates in standard peptide coupling chemistry to form stable amide linkages with incoming amino components. Lysine side-chain preservation under ε-acyl protection supports controlled formation of longer peptides and can be carried through to later selective deprotection steps for side-chain functionalization.
2. Protected Amino Acids
N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine is suitable for protected amino acid synthesis strategies that require orthogonal handling of α- and ε-amino groups. The Fmoc-protected α-amine provides a robust, removable protecting group compatible with common peptide synthesis conditions, whereas the ε-trifluoroacetyl group offers strong acyl protection that can be retained during multiple coupling cycles. The presence of a stereodefined L-lysine backbone supports stereochemically consistent peptide bond formation and downstream chiral integrity in assembled sequences. The compound can be employed as a defined intermediate for manufacturing-grade protected lysine reagents and for preparing custom protected amino acid building blocks used in fine chemical synthesis.
3. Side-Chain Functionalization
N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine supports side-chain modification workflows in peptidomimetics and chemical biology where lysine ε-nitrogen must be unmasked or transformed at a controlled stage. The ε-trifluoroacetamide functionality acts as a protected handle that can be selectively removed to generate a lysine ε-amino group for subsequent derivatization, including formation of urea, carbamate, sulfonamide, or other nitrogen-linked motifs. The Fmoc group can be deprotected independently to enable peptide coupling without premature exposure of the side-chain nucleophile, reducing cross-reactivity during multistep synthesis. The resulting lysine-containing intermediates can be converted into functionalized peptide analogs, enabling systematic exploration of charge, hydrogen-bonding, and conjugation patterns in amino acid chemistry.
4. Chemical Biology Probes
N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine is applicable to chemical biology research that uses lysine-bearing peptides and proteins for controlled labeling and molecular recognition studies. The protected ε-amide and Fmoc α-protection allow incorporation into peptide scaffolds while maintaining a defined, non-reactive side-chain during assembly, which is important for minimizing off-target modifications. Deprotection and subsequent coupling can generate lysine ε-functionalized conjugates compatible with affinity tags, crosslinkers, or reporter-bearing fragments used in biomolecule modification. The stereochemically defined lysine unit supports reproducible conjugate construction for downstream assays, analytical standards, and mechanistic studies of peptide-mediated interactions.
5. Pharmaceutical Manufacturing
N-α-Fmoc-N-ε-tritfluoroacetyl-L-lysine can be used in pharmaceutical manufacturing contexts focused on peptide and peptide-like intermediate preparation where controlled protection of lysine is required for scalable synthesis. The orthogonal Fmoc and trifl uoroacetyl protecting-group set supports predictable deprotection sequencing, enabling reliable conversion from protected building blocks to assembled peptide intermediates and later functionalized derivatives. The carboxylic acid functionality supports incorporation into peptide chains under manufacturing-compatible coupling chemistries, while the protected ε-amide helps manage side reactions during process steps. The compound thus functions as a chiral, protected lysine input for process chemistry intermediate generation and specialty chemical production of defined peptide materials.
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