Boc-D-Lys(Tfa)-OH is a protected amino acid derivative of D-lysine bearing an N-terminal Boc (tert-butoxycarbonyl) protecting group and a side-chain Nε-(trifluoroacetyl) (Tfa) acyl protection on the ε-amino functionality. The molecule contains both a free carboxylic acid group and a protected α-amino group, with the lysine side chain converted from a primary amine into a trifluoroacetamide that modulates nucleophilicity and chemoselectivity during peptide coupling steps. In peptide synthesis workflows, this orthogonally protected lysine analogue is used as a building block to control side-chain reactivity while enabling stepwise assembly of peptides or preparation of further lysine-derived intermediates for structure-activity and labeling studies.
CAT No: CP27613
CAS No:96561-04-5
Synonyms/Alias:96561-04-5;(R)-2-((tert-Butoxycarbonyl)amino)-6-(2,2,2-trifluoroacetamido)hexanoicacid;Boc-D-Lys(TFA)-OH;C13H21F3N2O5;AC1ODTO2;CTK8G1611;MolPort-020-003-801;ZINC1640316;4345AH;KM3426;AJ-28570;AK129316;AB0178400;KB-209691;Nalpha-Boc-Nepsilon-trifluoroacetyl-D-lysine;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[(2,2,2-trifluoroacetyl)amino]hexanoicacid
Boc-D-Lys(Tfa)-OH is a protected, stereodefined lysine building block featuring a Boc-protected alpha-amino group and a side-chain lysine protected as a trifluoroacetyl (Tfa) amide. This combination is commonly used to control chemoselectivity during peptide assembly, enabling stepwise incorporation of D-lysine residues while minimizing side-chain reactivity. The product is routinely selected by peptide chemists and medicinal chemistry teams that require a stable, isolable amino acid derivative for constructing D-amino acid-containing sequences and related pharmaceutical intermediates.
1. D-Lysine Peptide Building Block
Boc-D-Lys(Tfa)-OH is used as a lysine residue input for peptide synthesis workflows where D-configuration is required to probe structure-activity relationships, proteolytic stability, or conformational effects in peptide analogs. Peptide synthesis teams incorporate this protected amino acid into linear peptides and peptide segments to maintain orthogonal control of the side-chain amine via the Tfa protection while the Boc group enables selective activation/condensation under standard peptide assembly conditions. The derivative form is particularly valued when downstream purification and handling benefit from a protected, non-zwitterionic building block rather than a free amino acid.
2. Solid-Phase Peptide Segment Assembly
Boc-D-Lys(Tfa)-OH is frequently employed in custom peptide manufacturing and research-grade solid-phase peptide synthesis campaigns that require controlled lysine side-chain protection during iterative chain elongation. By keeping the lysine side-chain amide-protected, the reagent supports reliable coupling steps and reduces the likelihood of side reactions associated with unprotected ε-amines, which is important when synthesizing longer sequences or libraries containing multiple basic residues. Medicinal chemistry groups also use this building block to prepare D-lysine-containing segments that can be further modified after peptide assembly, depending on the selected deprotection and functionalization strategy.
3. Peptidomimetic and SAR Intermediate
Boc-D-Lys(Tfa)-OH supports the preparation of peptidomimetic scaffolds and structure-activity relationship (SAR) intermediates where a D-lysine motif is introduced as part of a defined synthetic sequence. Pharmaceutical intermediate development teams use this protected amino acid derivative to standardize the introduction of a basic side chain in a controlled fashion, enabling consistent downstream transformations during lead optimization. The Boc/Tfa protection pattern helps provide a predictable handle set for subsequent processing steps after peptide or peptidomimetic assembly, aligning with workflows that prioritize reproducible intermediate quality for scale-up and analog generation.
4. Stereocontrolled Amino Acid Derivative Synthesis
Boc-D-Lys(Tfa)-OH is also used as a stereocontrolled starting material for generating lysine-based derivatives that retain the D-configuration at the alpha carbon. Chemical biology and medicinal chemistry laboratories leverage such protected, stereodefined amino acid derivatives when they need a non-natural stereochemical element embedded into a larger synthetic target, such as D-lysine-containing conjugation precursors or specialized peptide fragments. The protected form simplifies handling and integration into multi-step synthetic routes, where isolable intermediates and minimized side-chain reactivity are essential for efficient downstream processing.
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