Ac-DL-Lys(Ac)-OH is an amino acid derivative of lysine bearing an N-terminal acetyl (Ac) group and an additional acetylated side-chain amide, placing it in the class of protected/derivatized lysine analogues used for peptide-related chemistry. The molecule contains an amino functionality and a carboxyl group while the ε-amino side chain is modified as an acetamide, and the "DL" designation indicates a racemic mixture of stereochemical forms at the α-carbon. Ac-DL-Lys(Ac)-OH is used as a defined, acetylated lysine building block or intermediate in peptide synthesis and in chemical labeling or analytical workflows where controlled side-chain acylation and reduced side-chain basicity are required.
CAT No: CP27046
CAS No:35436-74-9
Synonyms/Alias:2,6-diacetamidohexanoicacid;ZHZUEHHBTYJTKY-UHFFFAOYSA-N;35436-74-9;DL-Lysine,N2,N6-diacetyl-;Ac-DL-Lys(Ac)-OH;AC-DL-LYS-OH;N,N'-diacetyl-DL-lysine;AC-LYS(AC)-OH;AC1L3MW4;SCHEMBL2735591;Lysine,N2,N6-diacetyl-,DL-;N.alpha.,N.epsilon.-Diacetyl-DL-lysine;AM004860
Ac-DL-Lys(Ac)-OH is an acetylated lysine derivative supplied as a free amino acid building block in which the alpha-amino group is acetylated and the side-chain epsilon-amino group is also acetylated, giving a doubly N-acetylated, DL-configured lysine scaffold. This protected, acylated form is commonly used to introduce a lysine residue in peptide-related syntheses and to prepare lysine-containing intermediates where unprotected amines would otherwise interfere with coupling, derivatization, or analytical workflows.
1. Lysine-Residue Peptide Building
Ac-DL-Lys(Ac)-OH is used as a lysine-containing amino acid building block for preparing peptide fragments and peptide-like structures where both the alpha and epsilon amines must remain masked during assembly. Researchers in custom peptide synthesis and peptide chemistry often select this doubly acetylated lysine to avoid side reactions associated with free amine functionality while maintaining the correct lysine carbon framework for downstream coupling strategies. The DL stereochemical form supports workflows that do not require strict enantiopurity at the lysine center, such as exploratory structure-property studies, library synthesis, and intermediate generation for subsequent purification and characterization.
2. Amine-Blocked Derivatization Standard
Ac-DL-Lys(Ac)-OH is frequently employed as a chemically defined, amine-blocked lysine reference in analytical method development and derivatization optimization, particularly when acetylated lysine species are expected or when derivatization reagents target primary amines. Analytical chemists use such standards to validate derivatization efficiency, monitor recovery, and benchmark LC-MS or GC-MS behavior for lysine-containing analytes where uncontrolled amine reactivity would complicate quantitation. The presence of two acetyl groups provides a predictable chemical environment compared with free lysine, improving reproducibility when preparing calibration materials and troubleshooting derivatization conditions.
3. Pharmaceutical Intermediate Scaffold
Ac-DL-Lys(Ac)-OH serves as a practical intermediate scaffold for pharmaceutical intermediate development and specialty chemical manufacturing steps that require a lysine backbone while keeping amine groups protected as acetamides. Process and R&D teams use this type of building block to assemble larger molecules through reactions that are compatible with acylated amide functionality, while deferring introduction of reactive amines to later stages. In medicinal chemistry and process development, the doubly acetylated pattern helps control chemoselectivity by reducing competing nucleophilicity from the lysine side chain during the early stages of intermediate construction.
4. Protected Side-Chain Control
Ac-DL-Lys(Ac)-OH is used to control lysine side-chain reactivity in synthetic sequences and materials-related chemistry where the epsilon-amino group must not participate in side reactions. By keeping the lysine side chain as an acetylated amide, the compound supports more selective functionalization of other handles in multi-component syntheses, including orthogonal derivatization strategies that rely on the absence of free primary amines. This makes it a useful reagent for preparing lysine-containing intermediates for subsequent transformations, including stages where selective deprotection or later functional group installation is planned after the main coupling or assembly step.
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