Boc-L-Lys(N3)-OH*CHA is a protected, amino acid derivative featuring the lysine backbone bearing a Boc (tert-butoxycarbonyl) protecting group on the α-amino functionality and an azido substituent on the ε-amino side chain, with the "L" stereochemical designation indicating the chiral configuration at the α-carbon. The molecule contains both an α-carboxylic acid group and a side-chain azide (N3) functional handle, while the Boc group masks the α-amino to control chemoselectivity during stepwise coupling and to suppress side reactions involving the amine. In peptide chemistry and chemical biology workflows, the azide-bearing lysine analogue is used as a precursor for introducing a bioorthogonal azide handle for subsequent conjugation, labeling, or crosslinking steps, and the protected format supports incorporation into protected peptide intermediates under standard amino-acid coupling conditions.
CAT No: CP26071
CAS No:846549-33-5
Synonyms/Alias:846549-33-5;Boc-Lys(N3)-OH;SCHEMBL14439650;CTK2I5450;C11H20N4O4;0492AF;ZINC38528731;Hexanoicacid,6-azido-2-[[(1,1-dimethylethoxy)carbonyl]amino]-,(2S)-
Chemical Name:N-alpha-t-Butyloxycarbonyl-epsilon-azido-L-lysine, N-alpha-t-Butyloxycarbonyl-epsilon-azido-L-norleucine, (S)-2-t-Butyloxycarbonylamino-6-azidohexanoic acid cyclohexylamine
Boc-L-Lys(N3)-OH*CHA is a protected lysine derivative designed for peptide and chemical biology workflows, featuring an N3 (azide) functional group on the lysine side chain while the alpha-amino group is protected as a Boc carbamate. The presence of the azide enables downstream chemoselective labeling and conjugation chemistry, while the Boc protection supports controlled incorporation during peptide assembly. The "*CHA" component indicates an associated counterion/complex form that is commonly used to support handling and reactivity in synthetic and manufacturing settings.
1. Azide-Enabled Peptide Synthesis
Boc-L-Lys(N3)-OH*CHA is used as a lysine building block for assembling peptides where an azide handle is required for later functionalization. Peptide synthesis teams rely on the Boc-protected amino group to maintain compatibility with protected-amino-acid coupling strategies, while the side-chain azide provides a convenient functional group for post-synthetic modification. This makes the reagent particularly valuable for producing azide-bearing peptide segments for mapping studies, affinity reagents, and modular peptide constructs that need orthogonal downstream labeling without altering the peptide backbone.
2. Click Conjugation Labeling
Boc-L-Lys(N3)-OH*CHA is widely selected for preparing azide-functional peptides and peptide conjugates that undergo azide-alkyne cycloaddition to install dyes, affinity tags, or biophysical reporters. Chemical biology groups use the lysine side-chain azide as a stable, transportable reactive handle that can be introduced during peptide synthesis and then converted under click conditions to generate labeled biomolecules for assay development and reagent screening. This approach supports streamlined workflows where the azide is introduced at the building-block stage, reducing the need for late-stage modification of complex peptide mixtures.
3. Bioconjugate and Surface Functionalization
Boc-L-Lys(N3)-OH*CHA serves as a practical precursor for building azide-containing peptide linkers used in bioconjugation and immobilization strategies. Materials and protein engineering laboratories use azide-bearing lysine-containing peptides to generate conjugates for attaching biomolecules to surfaces or polymers through click-compatible chemistries, enabling controlled presentation of ligands or capture elements. The combination of a protected amino acid for synthesis and a side-chain azide for coupling helps teams design modular constructs where the peptide provides the targeting or recognition motif while the azide enables subsequent attachment to a chosen material platform.
4. Pharmaceutical Intermediate Building Block
Boc-L-Lys(N3)-OH*CHA is also used as an intermediate building block in medicinal chemistry and process development programs that require an azide-functional lysine unit for constructing larger molecules. Synthetic teams incorporate this reagent into protected frameworks to introduce a handle for later derivatization, allowing flexible routing toward peptidomimetic scaffolds, linker systems, or other azide-to-functional-group transformations. The protected lysine scaffold supports controlled assembly of complex intermediates, while the azide functionality provides a downstream "conversion point" for generating final structures used in research-scale lead optimization and specialty chemical manufacturing.
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