Boc-D-Dab(Z)-OH DCHA is a Boc-protected D-configured amino acid derivative of 2,4-diaminobutyric acid bearing a Z (benzyloxycarbonyl) protecting group on one side-chain amino functionality, with a free carboxylic acid group and the backbone amino protected as a carbamate. The molecule contains a tert-butoxycarbonyl (Boc) group on the α-amino position, a Z-protected side-chain amine that reduces undesired nucleophilicity during coupling steps, and a D-configuration at the stereogenic center as indicated by the name, while DCHA denotes formation as a dicyclohexylamine salt that can modulate handling and solubility. In peptide chemistry, this protected amino acid salt is employed as a stepwise building block for incorporating a diamino side chain into protected peptide intermediates and for preparing peptide analogues and chemical probes where controlled side-chain deprotection and orthogonal amine reactivity are required.
CAT No: CP05317
CAS No:101854-42-6
Synonyms/Alias:N-α-Boc-N-γ-Z-D-2,4-diaminobutyric acid dicyclohexylamine salt;
Boc-D-Dab(Z)-OH DCHA is a Boc-protected D-2,4-diaminobutyric acid derivative bearing a Z-configured side-chain protection and supplied as a dicyclohexylamine (DCHA) salt. The molecule contains a stereogenic center at the D-Dab backbone, a tert-butoxycarbonyl (Boc) group that modulates the α-amino reactivity during peptide coupling, and a protected side-chain functionality that can be unmasked or transformed under controlled conditions. The carboxylic acid (-CO2H) enables conversion to activated esters or coupling-ready forms, while the salt form improves handling characteristics for synthetic workflows. The combination of defined stereochemistry, orthogonal protection, and acid functionality makes the compound suitable as a chiral amino acid intermediate and peptide building block for downstream derivatization and analog construction.
1. Peptide Synthesis
Boc-D-Dab(Z)-OH DCHA is applied in peptide synthesis workflows where orthogonally protected amino acid building blocks are required for controlled amide bond formation. The Boc group on the α-amino functionality supports selective peptide coupling while limiting side reactions from the amino-bearing Dab core, and the protected side-chain motif can be carried through coupling steps to preserve chemoselectivity. The free carboxylic acid enables standard peptide coupling strategies after conversion to an activated carboxylate, supporting incorporation of the D-configured Dab residue into peptide chains. The resulting peptides and peptide fragments can be used for library generation, structure-activity relationship studies, and mechanistic investigations in peptide science and chemical biology.
2. Peptidomimetic Construction
Boc-D-Dab(Z)-OH DCHA serves in peptidomimetic and constrained scaffold design where the D-Dab stereocenter and side-chain nitrogen architecture can tune conformational preferences and binding interactions. The protected amine/side-chain functionality enables stepwise unveiling or functional group transformation to introduce amide, urea, or other nitrogen-containing motifs during analog assembly. The Boc-protected amino acid format supports sequential coupling and late-stage diversification, enabling access to peptidomimetic series with controlled stereochemistry and defined functional group placement. Downstream, the compound can be used to generate fragment-like building blocks for medicinal chemistry exploration and for constructing amino acid-derived molecular scaffolds with reproducible substitution patterns.
3. Side-Chain Functionalization
Boc-D-Dab(Z)-OH DCHA is utilized for side-chain functionalization strategies that rely on orthogonal protection of amino functionalities on the Dab backbone. The Z-protected side-chain element can be manipulated to introduce reactive handles for further derivatization, including conversion to additional amide linkages, incorporation into heterocycle-forming intermediates, or preparation of conjugation-ready derivatives. The presence of a carboxylic acid group allows formation of activated intermediates that can be used to append functional groups while maintaining stereochemical integrity at the D-center. The DCHA salt form can also support reproducible handling and consistent reactivity profiles during multi-step synthesis of functionalized amino acid derivatives.
4. Chemical Biology Probes
Boc-D-Dab(Z)-OH DCHA is suitable for chemical biology research that requires amino acid-based probes with defined stereochemistry and protected functional groups for controlled conjugation. The Boc-protected α-amino group and the side-chain protection enable assembly of peptide-like constructs that can later be converted into labeling reagents or affinity handles under conditions compatible with other functional groups. The carboxylic acid functionality supports incorporation into probe scaffolds through peptide coupling chemistry, enabling attachment to targeting motifs or reporter-bearing fragments. The stereodefined D-Dab residue can be incorporated into probe designs to probe recognition, binding specificity, or structure-dependent interactions in biological systems while maintaining synthetic control over functional group exposure.
5. Pharmaceutical Manufacturing Intermediates
Boc-D-Dab(Z)-OH DCHA is relevant to pharmaceutical intermediate preparation where protected amino acid derivatives are manufactured as controlled, coupling-ready inputs for downstream API or intermediate synthesis. The Boc-protected amino functionality supports predictable behavior under peptide coupling and deprotection sequences, and the defined D-configuration helps ensure stereochemical consistency across batch-to-batch manufacturing. The carboxylic acid enables conversion to activated forms used in industrial peptide chemistry, while the orthogonal side-chain protection supports stepwise processing without premature crosslinking or undesired side reactions. The DCHA salt form can be applied to improve solid-state handling and facilitate consistent formulation of the intermediate for process chemistry routes.
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