Boc-D-Dap(Z)-OH·DCHA is a protected, stereochemically specified amino acid derivative of diaminopropionic acid (Dap) in which the α-amino group is masked as a Boc carbamate and the side-chain amino group is protected as a Z (benzyloxycarbonyl) carbamate. The molecule contains a free C-terminal carboxylic acid (-CO2H) and bears a Dap backbone configured as D at the stereocenter indicated by the product name, while the "·DCHA" denotes association with dicyclohexylamine (DCHA) as a salt form that can influence handling and solubility. In peptide synthesis workflows, the orthogonal Boc and Z protections support stepwise chemoselective deprotection and coupling strategies to incorporate the protected diamino acid residue into peptide and peptidomimetic targets, and the protected diamine functionality provides a controlled handle for downstream functionalization after deprotection.
CAT No: CP05822
CAS No:81306-94-7
Synonyms/Alias:N-α-Boc-N-β-Z-D-2,3-diaminopropionic acid dicyclohexylamine salt;81306-94-7;Dicyclohexylamine3-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoate;SCHEMBL7740099;CTK8C0034;MolPort-023-331-552;RPWGTQRQPVPFKR-UHFFFAOYSA-N;ANW-63920;AKOS016003876;AK-61278;AM006439;TC-152665;4CH-024001;N-a-Boc-N-b-Z-D-2,3-diaminopropionicaciddicyclohexylaminesalt;3-{[(BENZYLOXY)CARBONYL]AMINO}-2-[(TERT-BUTOXYCARBONYL)AMINO]PROPANOICACID;DICHA;3-benzyloxycarbonylamino-2-tert-butoxycarbonylaminopropionicaciddicyclohexylamine
Boc-D-Dap(Z)-OH·DCHA is a chiral, N-Boc-protected amino acid derivative of D-2,3-diaminopropanoic acid (D-Dap) bearing a Z-protected side-chain amino functionality and supplied as a salt complex with DCHA. The molecule contains a stereogenic center at the alpha carbon, a tert-butoxycarbonyl (Boc) carbamate on the alpha amine, and a benzyloxycarbonyl-type (Z) protection pattern on the additional amino group, together with a free carboxylic acid that supports peptide coupling chemistry. The salt form with dicyclohexylamine (DCHA) can influence crystallinity and handling while preserving the underlying protected amino acid reactivity profile. Boc and Z protection strategies enable orthogonal deprotection logic for sequential functionalization, peptide assembly, and downstream conversion into amino acid building blocks or side-chain modified derivatives.
1. Peptide Synthesis
Boc-D-Dap(Z)-OH·DCHA is used in peptide building block preparation where orthogonally protected diamino acid functionality supports controlled peptide coupling and selective deprotection. The Boc-protected alpha amine and Z-protected side-chain amino group allow installation of the residue into peptide chains while minimizing side reactions from the diamine during coupling and activation steps. The free carboxylic acid participates in standard peptide coupling chemistries to form amide bonds, enabling construction of peptides containing D-configured diamino motifs for conformational control and stability. The protected diamine architecture can be carried through iterative synthesis before unmasking to generate cationic or functional side-chain variants for subsequent conjugation or structure-function studies.
2. Side-Chain Functionalization
Boc-D-Dap(Z)-OH·DCHA is suitable for amino acid derivatization and side-chain functionalization workflows that require selective exposure of one amine under controlled protecting-group removal. The presence of two protected amino sites, one as a Boc carbamate and the other as a Z-protected group, enables stepwise conversion into mono-functionalized or bifunctional Dap derivatives for crosslinking, linker installation, or attachment of electrophiles. The stereochemical integrity of the D-center supports reproducible spatial presentation of the diamine side chain in downstream conjugates. The resulting deprotected or partially deprotected intermediates can be applied to generate peptide analogs, chemical probes, and reactive handles for biomolecule modification and synthetic scaffold diversification.
3. Chemical Biology Probes
Boc-D-Dap(Z)-OH·DCHA supports chemical biology research where protected diamino acid residues serve as incorporation points for fluorescent tags, affinity handles, or reactive groups in peptide-based probes. The orthogonal protection pattern helps manage chemoselectivity when preparing labeled peptide conjugates, since the diamine functionality can be unmasked in a planned sequence to match labeling chemistry. The D-configuration can be leveraged to tune resistance to proteolysis and to modulate binding conformations in probe scaffolds, while the carboxylic acid enables straightforward integration into peptide sequences. Downstream derivatives generated from deprotected amines can function as coupling partners for bioconjugation reagents, enabling targeted labeling strategies in biochemical assays and molecular recognition studies.
4. Protected Amino Acid Chemistry
Boc-D-Dap(Z)-OH·DCHA is employed as a chiral, protected amino acid intermediate for protected amino acid synthesis and orthogonal deprotection planning in fine chemical and peptide manufacturing contexts. The Boc carbamate and Z-protection pattern provide a practical framework for sequential unmasking, allowing selective generation of a free amine for subsequent derivatization while retaining the other protection as a temporary safeguard. The free carboxylic acid supports conversion to activated esters or coupling-ready forms during process design, while the DCHA salt form can aid handling and reproducible material preparation. The compound's protected diamino acid structure makes it a useful intermediate for producing a range of Dap-containing building blocks, including C-terminal modified residues and side-chain functional amino acid analogs.
5. Pharmaceutical Intermediate Preparation
Boc-D-Dap(Z)-OH·DCHA can be applied in pharmaceutical intermediate preparation where diamino acid motifs are incorporated into peptidomimetic or peptide-like structures used in medicinal chemistry programs. The protected amine set supports controlled assembly of amide-linked fragments and reduces undesired polymerization or overreaction during synthetic steps that involve electrophilic activation of the carboxyl group. The stereogenic D-center and the orthogonality between Boc and Z protection enable route designs that align with sequential functional group transformations, including late-stage side-chain installation. The resulting intermediates can feed into downstream synthesis of cationic or functionalized peptidomimetic scaffolds and related research-grade materials used for SAR studies and process development.
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