Boc-Lys(4-nitro-Z)-OH is a protected lysine derivative featuring a Boc-protected α-amino group and a side-chain ε-amino group capped with a 4-nitro-Z substituent, where the "Z" group denotes a benzyloxycarbonyl-type carbamate. The molecule contains a free carboxylic acid functionality and bears the lysine backbone with the side chain presenting the protected ε-nitrogen, while the benzyloxycarbonyl-derived substituent and the Boc group control chemoselectivity by suppressing undesired amine reactivity during stepwise coupling. In peptide synthesis workflows, it functions as a protected amino acid building block for introducing a lysine residue bearing a nitro-substituted Z-protected side-chain handle for downstream derivatization, conjugation, or analytical labeling strategies.
CAT No: CP26823
CAS No:22601-53-2
Synonyms/Alias:22601-53-2;(S)-2-((tert-Butoxycarbonyl)amino)-6-((((4-nitrobenzyl)oxy)carbonyl)amino)hexanoicacid;Boc-Lys(4-nitro-Z)-OH;SCHEMBL10077062;MolPort-027-836-732;C19H27N3O8;1372AB;ZINC15722340;AKOS016011453;AJ-67851;AK120850;KB-210907
Boc-Lys(4-nitro-Z)-OH is a protected lysine derivative designed for peptide synthesis workflows, featuring an N-terminal Boc protecting group and a side-chain-protected lysine with a 4-nitro-Z protecting motif. The lysine ε-amino functionality is masked to preserve chemoselectivity during chain assembly, while the nitro-substituted Z-type side-chain protection supports downstream deprotection strategies used in the preparation of lysine-containing peptides and peptide segments. This reagent is typically handled as a stable, solid building block for stepwise synthesis where controlled liberation of the lysine side chain is required for subsequent coupling, modification, or final peptide assembly.
1. Solid-Phase Peptide Synthesis
Boc-Lys(4-nitro-Z)-OH is used as an Fmoc-free, Boc-protected lysine building block for constructing lysine-containing peptide sequences in solid-phase peptide synthesis, especially when the synthesis strategy relies on Boc compatibility and controlled deprotection timing. Peptide synthesis groups employ this reagent to ensure that the ε-amino group remains inactive during backbone elongation, allowing selective coupling at the growing peptide N-terminus without side reactions from free lysine. The presence of the 4-nitro-Z side-chain protection supports workflows where lysine functionality must be preserved through multiple coupling/deprotection cycles and revealed at a defined stage for subsequent transformations or final product generation.
2. Lysine Side-Chain Functional Peptides
Boc-Lys(4-nitro-Z)-OH is applied in the preparation of peptides that require later lysine side-chain derivatization, including peptide segments intended for chemical modification after assembly. In peptide chemistry and chemical biology development, researchers often protect lysine during synthesis to prevent heterogeneous outcomes, then introduce side-chain reactivity in a controlled manner after the peptide backbone is completed. This reagent's protected ε-amino group enables the production of defined lysine-containing intermediates that can be carried forward into downstream derivatization steps, such as generating lysine-bearing conjugation handles or preparing peptide variants for structure-activity relationship studies where side-chain chemistry is varied systematically.
3. Pharmaceutical Intermediate Peptide Segments
Boc-Lys(4-nitro-Z)-OH is frequently selected by teams developing peptide-based pharmaceutical intermediates and custom peptide manufacturing programs that require robust control over lysine protection during multi-step synthesis. Pharmaceutical intermediate development commonly emphasizes reproducibility of protected amino acid incorporation and minimized side reactions during segment assembly, particularly for sequences containing lysine residues. By using this Boc-protected lysine building block with a defined side-chain protection pattern, developers can streamline the preparation of lysine-containing peptide segments that later undergo standardized deprotection and coupling operations to reach target intermediate structures used in larger synthesis campaigns.
4. Peptide Library Building Blocks
Boc-Lys(4-nitro-Z)-OH supports parallel synthesis and peptide library construction where lysine positions must be kept consistent across many analogs while allowing controlled variation in later stages. In academic peptide engineering and screening-oriented chemistry, this reagent helps maintain uniform protection of the lysine side chain during library assembly, reducing sequence-dependent heterogeneity caused by premature ε-amino reactivity. Researchers use it to generate lysine-containing peptide precursors that can be processed into multiple analogs with defined side-chain states, enabling systematic exploration of how lysine chemistry impacts peptide properties such as stability, solubility, or binding behavior in non-clinical assay contexts.
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