Ac-Dab(Boc)-OH contains an N-acetylated 2,4-diaminobutyric acid (Dab) core bearing a Boc-protected amino group, placing it in the class of protected amino acid derivatives used for peptide-related synthesis. The molecule presents a free carboxylic acid functionality alongside an N-acetylated amide and a Boc carbamate, with the remaining amino functionality providing a chemoselective handle for further coupling chemistry while the Boc group suppresses undesired reactions of that side-chain nitrogen. In synthetic workflows, it is employed as a protected amino acid building block to introduce Dab residues into peptides or peptide analogues under conditions that require orthogonal protection and controlled reactivity of the amine groups.
CAT No: CP26710
CAS No:201351-32-8
Synonyms/Alias:AC-DAB(BOC)-OH;201351-32-8;Nalpha-Ac-Ngamma-Boc-L-2,4-diaminobutyricacid;SCHEMBL16945135;CTK8E7036;BUTANOICACID,2-(ACETYLAMINO)-4-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-,(2S)-;ZINC2560342;6079AH;AKOS025294842;RT-014642;K-5888
Ac-Dab(Boc)-OH is an N-acetylated, Boc-protected derivative of 2,3-diaminobutyric acid (Dab), supplied as a protected amino acid building block for peptide and peptidomimetic synthesis workflows. The N-acetyl group and Boc protection provide controlled reactivity during stepwise assembly, while the diamino side-chain functionality supports downstream derivatization or incorporation into defined peptide segments. This protected format is commonly used when a stable, non-gelling intermediate is needed for reliable coupling and for maintaining side-chain protection throughout multi-step synthesis and purification.
1. Peptide Segment Building
Ac-Dab(Boc)-OH is used by custom peptide synthesis groups and medicinal chemistry teams as a protected amino acid building block to assemble peptide segments that require a protected Dab residue. The N-acetylation and Boc protection help maintain chemoselectivity during coupling steps, enabling consistent incorporation into solution-phase or solid-phase workflows where side-chain reactivity must be suppressed until the intended stage of synthesis. Researchers rely on this derivative to prepare defined peptidomimetics and peptide analogs for structure-activity relationship studies, where precise control over protecting-group patterns is critical for reproducible purification and fragment coupling.
2. Peptidomimetic Intermediate Development
Ac-Dab(Boc)-OH is frequently selected as a pharmaceutical intermediate building block for constructing peptidomimetic scaffolds that incorporate Dab-like diamino functionality. Process and development chemists use N-acetylated, Boc-protected derivatives to manage reactivity during intermediate elaboration, particularly when the target synthesis requires selective deprotection at a later stage to reveal the diamino functionality for subsequent transformations. This makes the compound a practical choice for preparing advanced intermediates used in library synthesis, analog generation, and downstream derivatization strategies that depend on controlled exposure of the side-chain amines.
3. Protected Side-Chain Functionalization
Ac-Dab(Boc)-OH supports workflows where the protected diamino side-chain must be carried through early synthetic steps and then converted into a specific functionalized form. Chemical biology and peptide engineering groups use this derivative to prepare defined intermediates for later modification of the Dab side-chain, enabling controlled attachment of additional substituents or incorporation into specialized peptide constructs. The protected format helps reduce side reactions during earlier coupling and purification operations, improving reproducibility when the downstream plan requires selective side-chain manipulation after the peptide framework is assembled.
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