Ac-Lys(Ac)-OH is an N-acetylated lysine derivative in which the ε-amino group is additionally acetylated, yielding a protected, substituted amino acid bearing a side-chain with an acetylated primary amide rather than a free amine. The molecule contains an N-acetylated α-amino functionality and a carboxylic acid (-COOH) at the α-position, with both amino groups converted to amide linkages that suppress typical amine reactivity and reduce opportunities for undesired side reactions during coupling chemistry. As a defined, doubly acylated lysine building block, it is used in peptide-related synthesis and analytical workflows where controlled handling of lysine's ε-position and minimized free amine behavior are required, such as preparing protected lysine-containing intermediates or reference standards for amino acid derivative characterization.
CAT No: CP27153
CAS No:499-86-5
Synonyms/Alias:AC-LYS(AC)-OH;499-86-5;N,N'-diacetyl-L-lysine;Lysine,N2,N6-diacetyl-;SCHEMBL1200060;CHEMBL1221839;CTK1C1071;ZHZUEHHBTYJTKY-VIFPVBQESA-N;(S)-2,6-DiacetamidohexanoicAcid;ZINC2560345;6097AH;AKOS025289480;AK170239;K-9257
Ac-Lys(Ac)-OH is an N-acetylated lysine derivative bearing an additional acetyl group on the side-chain amino functionality, providing a doubly acylated, non-free amine amino acid suitable for downstream peptide and amide-forming chemistry. This protected lysine form reduces undesired amine reactivity during coupling steps and is commonly handled as a stable, well-defined building block for preparing acetylated peptide segments and lysine-containing amide derivatives. Researchers use it when maintaining an acetylated lysine motif is important for controlling charge state, minimizing side reactions, or matching the chemistry of acetyl-lysine-like patterns in synthetic targets.
1. Acetylated Peptide Building Blocks
Ac-Lys(Ac)-OH is used as a lysine-containing building block for assembling peptides or peptide fragments that require acetylated amine functionalities at both the α-amino terminus and the lysine side chain. Peptide synthesis groups and custom peptide manufacturers select this reagent when they need to preserve an acetylated lysine motif through the coupling workflow, reducing the chance of side-chain deprotection or uncontrolled amine participation. The doubly acylated structure also supports cleaner segment condensation and downstream purification by limiting free amine reactivity.
2. Amide-Linked Intermediate Synthesis
Ac-Lys(Ac)-OH serves as a defined amino acid intermediate for preparing amide-linked derivatives where lysine's amine groups must be masked as acetyl amides during the key bond-forming step. Process development chemists and medicinal chemistry teams often incorporate such protected lysine units into larger scaffolds by converting the carboxyl group into activated coupling partners while retaining the acetylated nitrogen functionalities to control chemoselectivity. This makes the reagent useful for constructing acetylated lysine analogs, side-chain-modified amide linkers, and other intermediate structures that require predictable reactivity profiles.
3. Chemical Biology Reference Materials
Ac-Lys(Ac)-OH is commonly used in chemical biology and analytical method development contexts where acetyl-lysine-like chemistry needs to be represented in a synthetic standard or probe precursor. Researchers may prepare acetylated lysine-containing peptides or small molecules from this building block to support comparative LC-MS workflows, calibration strategies, or method qualification studies that track amide-stable, acylated nitrogen patterns. The reagent's protected amine functionality helps ensure that the synthetic reference maintains the intended acetylated motif without introducing competing reactive amine sites during derivatization and analysis.
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