Boc-Dab-OtBu · HCl is a protected amino acid derivative of 2,4-diaminobutyric acid (Dab), featuring a Boc-protected amino group and a tert-butyl ester at the carboxyl terminus. The molecule presents two amino functionalities on the side chain, while the "· HCl" indicates formation of a hydrochloride salt that protonates one or more basic nitrogens to control solubility and handling during synthesis. In peptide chemistry and related amide-bond construction, this protected Dab building block supports stepwise incorporation of the diamino side chain into larger peptide or peptidomimetic frameworks while reducing undesired side reactions from free amines and the carboxyl group.
CAT No: CP26584
CAS No:190447-69-9
Synonyms/Alias:190447-69-9;(S)-tert-Butyl4-amino-2-((tert-butoxycarbonyl)amino)butanoate;SCHEMBL2620497;VTAQKRDOQHUEKC-VIFPVBQESA-N;ZINC2392269;AKOS025287081;AK167048;Butanoicacid,4-amino-2-[[(1,1-dimethylethoxy)carbonyl]amino]-,1,1-dimethylethylester,(2S)-;(S)-tert-butyl4-amino-2-(tert-butoxycarbonylamino)butanoate
Boc-Dab-OtBu · HCl is a protected, stereochemically defined amino acid derivative featuring a tert-butyl ester (OtBu) and a Boc-protected amino group, supplied as the hydrochloride salt for improved handling and compatibility with peptide synthesis workflows. The side chain of Dab (2,4-diaminobutyric acid motif) makes it a practical building block for assembling polyamide frameworks where the protected functionality is carried through condensation steps and later unveiled under controlled deprotection conditions. This protected format is commonly selected by peptide and medicinal chemistry teams when they need a robust intermediate that can be incorporated into larger protected sequences with minimized side reactions.
1. Solid-Phase Peptide Synthesis
Boc-Dab-OtBu · HCl is used in solid-phase peptide synthesis by peptide chemists who require a protected Dab residue that remains stable under standard coupling conditions while the Boc group and tert-butyl ester protect the functional sites during chain assembly. The hydrochloride salt form supports reliable reagent handling and can simplify preparation of coupling-ready solutions for automated or semi-automated workflows. This product is particularly relevant when building protected peptide segments for subsequent global deprotection and purification, enabling consistent incorporation of the Dab-derived functionality into target peptides or peptide-like scaffolds.
2. Peptide Segment Building Block
Boc-Dab-OtBu · HCl serves as a peptide segment building block for solution-phase peptide synthesis and fragment condensation strategies, where protected amino acid derivatives are assembled into longer sequences prior to final deprotection. Researchers in medicinal chemistry and custom peptide manufacturing often select this specific protection pattern to manage reactivity during intermediate formation, especially when the sequence design requires careful control over amide bond formation and ester handling. The protected amino and carboxyl functionalities allow the Dab residue to be carried through condensation steps as a defined unit, supporting reproducible synthesis of protected intermediates for downstream purification and characterization.
3. Pharmaceutical Intermediate Development
Boc-Dab-OtBu · HCl is frequently employed as a pharmaceutical intermediate in the preparation of protected peptidomimetic structures and backbone-modified building blocks used in lead optimization programs. Process development groups and synthetic chemistry teams value the defined protection scheme for integrating the Dab-derived motif into larger scaffolds while maintaining functional-group compatibility during stepwise assembly. The hydrochloride salt form is also helpful for workflow practicality in intermediate manufacturing, where consistent reagent handling and reduced variability in reactive species can support scalable synthesis of protected intermediates destined for later functionalization or deprotection.
4. Protected Amino Acid Derivative Libraries
Boc-Dab-OtBu · HCl is used to expand protected amino acid derivative libraries for structure-activity relationship studies, where chemists generate series of related peptide-like compounds that differ by residue composition and protected-group patterns. In research settings, this building block enables systematic variation of the Dab-containing segment while keeping the reactive sites masked during parallel synthesis and purification. Teams performing combinatorial peptide assembly or iterative analogue synthesis rely on such protected derivatives to maintain uniformity across analogs, improving comparability of downstream analytical characterization and structure-property evaluation.
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