Boc-D-Dap(Boc)-OH*DCHA is a protected amino acid derivative featuring a diaminopropyl (Dap) backbone in which both the alpha-amino group and the side-chain amino functionality are masked as Boc (tert-butoxycarbonyl) carbamates, while the carboxyl group remains present as a free acid (-CO2H). The molecule bears the stereochemical designation "D" for the Dap center as indicated in the name, and the "*DCHA" denotes association with dicyclohexylamine (DCHA) as a salt form that modulates handling and physicochemical properties relative to the free base. In peptide chemistry, the dual Boc protection pattern provides orthogonal chemoselectivity for stepwise construction of peptide chains or for preparing more complex amino acid building blocks, where controlled deprotection can expose the primary amines for subsequent coupling, conjugation, or labeling workflows.
CAT No: CP25411
CAS No:159652-30-9
Synonyms/Alias:N-alpha-N-beta-Bis-Boc-D-2,3-diaminopropionic acid*DCHA;Boc-D-Dpr(Boc)*DCHA;Boc-D-Dapa(Boc)*DCHA
Chemical Name:N-alpha,N-beta-Bis-t-butyloxycarbonyl-D-2,3-diaminopropionic acid cyclohexylamine
Boc-D-Dap(Boc)-OH*DCHA is a protected, stereochemically defined diaminopropionic acid derivative bearing Boc-protected amino functionalities and a DCHA counterion, provided as a salt form to support handling and downstream peptide synthesis workflows. The presence of two Boc groups and the defined D-configuration makes this reagent particularly useful for assembling protected peptide segments where controlled deprotection and amide bond formation are required. In practice, it is selected by peptide chemists and process developers to introduce a protected Dap residue with predictable reactivity and compatibility with standard protected-amino-acid coupling strategies.
1. Solid-Phase Peptide Synthesis
Boc-D-Dap(Boc)-OH*DCHA is used by peptide synthesis groups to incorporate a protected Dap unit into peptide chains while maintaining orthogonal control over the amine functionality during chain assembly. The Boc-protected side-chain amine and Boc-protected backbone amino group help prevent undesired branching or side reactions during coupling cycles, enabling cleaner formation of the target amide linkages. Peptide manufacturers and academic peptide cores often select this salt form to improve practical reagent handling and reproducible coupling performance in automated solid-phase peptide synthesis workflows.
2. Protected Segment Building Block
Boc-D-Dap(Boc)-OH*DCHA serves as a reliable protected amino acid building block for solution-phase segment condensation and the preparation of intermediate peptide fragments containing a Dap motif. The dual Boc protection pattern supports controlled downstream deprotection strategies when the Dap side-chain needs to be unveiled at a later stage for further functionalization, conjugation, or to generate a specific reactive amine in the assembled intermediate. Pharmaceutical intermediate development teams frequently use such protected diaminopropionic reagents to manage chemoselectivity across multi-step peptide assembly and purification workflows.
3. Amine-Functionalized Peptide Derivatives
Boc-D-Dap(Boc)-OH*DCHA is commonly selected when the final target requires a defined, amine-rich peptide architecture that can be further modified after peptide assembly. The protected Dap residue provides a handle for later conversion to free amines under deprotection conditions, supporting downstream preparation of amine-functionalized peptide derivatives used in chemical biology and materials-oriented labeling strategies. Researchers developing peptide-based scaffolds for surface immobilization or for constructing multivalent binding/interaction motifs often rely on this reagent to ensure that the Dap functionality is introduced in a controlled, protected form during synthesis rather than as an unprotected diamine that would complicate assembly.
4. Peptide Library and SAR Intermediates
Boc-D-Dap(Boc)-OH*DCHA is also applied in peptide library construction and structure-activity relationship intermediate preparation where a consistent protected Dap unit is needed across multiple analogs. By standardizing the incorporation of a Boc-protected Dap building block, synthesis teams can reduce variability in side-chain reactivity and improve comparability of analogs that differ at other positions. Medicinal chemistry and process development groups use this type of protected amino acid reagent to streamline parallel synthesis of Dap-containing peptide candidates and to generate well-defined intermediates for subsequent derivatization steps.
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