Ac-Lys(Boc)-OH is an N-acetylated ε-Boc-protected lysine derivative bearing both an amino acid backbone and a protected side-chain amine, placing it in the class of protected amino acid derivatives used for peptide-related synthesis. The molecule contains a terminal carboxylic acid functional group and a free α-amino group while the lysine ε-amino is masked as a tert-butoxycarbonyl (Boc) carbamate, which suppresses side reactions from the side-chain nucleophile during coupling steps. In synthetic workflows, this protected analogue functions as a precursor for stepwise incorporation of lysine residues into peptides and for preparing more complex lysine-containing amino acid and peptide derivatives under chemoselective conditions.
CAT No: CP26838
CAS No:23500-04-1
Synonyms/Alias:23500-04-1;(S)-2-Acetamido-6-((tert-butoxycarbonyl)amino)hexanoicacid;Ac-Lys(Boc)-OH;Acetyl-Nepsilon-Boc-L-lysine;SCHEMBL10254699;CTK8B2977;MolPort-020-003-824;ZINC2560346;ANW-41536;AKOS015999018;AJ-40558;AK-90640;KB-211049;TC-130281;ST24020809;V4567;B-8056
Ac-Lys(Boc)-OH is an N-acetyl protected lysine building block featuring a Boc-protected side-chain amino group, providing orthogonal protection patterns commonly leveraged in peptide and intermediate synthesis workflows. The free carboxylic acid makes it a practical precursor for downstream coupling steps, while the protected ε-amino functionality helps control chemoselectivity during multistep assembly of lysine-containing sequences. Researchers typically select this protected lysine derivative when they need to introduce lysine residues with suppressed side-chain reactivity and controlled N-terminus behavior in segment condensation or protected-amino-acid chemistry.
1. Peptide Segment Coupling
Ac-Lys(Boc)-OH is used as a protected lysine unit in peptide assembly where the N-acetyl group and Boc-protected ε-amino group help minimize side reactions during coupling and purification. Peptide synthesis groups that build lysine-containing segments for custom peptide manufacturing often rely on this derivative to maintain side-chain protection integrity through iterative bond-forming steps, supporting reliable incorporation of lysine in protected form. The presence of a free C-terminal carboxylic acid enables it to be converted into activated coupling partners within standard peptide workflows used in academic and industrial peptide chemistry.
2. Lysine Side-Chain Controlled Synthesis
Ac-Lys(Boc)-OH supports chemoselective handling of lysine in solution-phase or convergent synthesis strategies by keeping the ε-amino group masked as a Boc carbamate. Medicinal chemistry teams preparing lysine-rich intermediates and peptide analogs frequently choose this protection scheme to prevent premature side-chain amide formation or cross-reaction when assembling adjacent residues or performing selective functional group manipulations. By retaining the side-chain in a protected state, the reagent helps maintain reaction selectivity across multistep sequences where lysine's two amino functionalities would otherwise complicate downstream transformations.
3. Pharmaceutical Intermediate Building Block
Ac-Lys(Boc)-OH is frequently used in the preparation of protected lysine-containing pharmaceutical intermediates, including advanced fragments that later require controlled deprotection and functionalization. Process development and specialty chemical manufacturers value this type of protected amino acid derivative because it provides a defined, stable intermediate form for further derivatization while keeping reactive amino groups protected until the intended stage of synthesis. The combination of N-acetyl protection and Boc-protected ε-amino functionality aligns with common intermediate design practices that prioritize stepwise control over reactivity and purification robustness.
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