Boc-D-Aza-OH*CHA is a Boc-protected amino acid derivative featuring a D-configuration at the amino acid center and a non-proteinogenic "aza" motif that replaces a conventional carbon atom within the side-chain framework. The molecule bears a tert-butoxycarbonyl (Boc) carbamate protecting group on the amino functionality and a free carboxylic acid, with the aza-containing side chain providing altered hydrogen-bonding and steric properties relative to standard amino acids. In peptide and peptidomimetic synthesis, it is used as a protected building block to introduce the aza-modified residue into stepwise coupling workflows while the Boc group helps control chemoselectivity by preventing unprotected amine reactivity during assembly.
CAT No: CP25636
CAS No:225780-77-8
Synonyms/Alias:Boc-D-Dap(N3)-OH*CHA;Boc-D-beta-azidoalanine cyclohexylamine;N-alpha-t-Butyloxycarbonyl-3-azido-D-alanine cyclohexylamine
Chemical Name:Boc-D-Aza-OH, Boc-D-beta-azidoalanine, N-alpha-t-Butyloxycarbonyl-3-azido-D-alanine, (R)-2-t-Butyloxycarbonylamino-3-azidopropanoic acid cyclohexylamine
Boc-D-Aza-OH*CHA is a D-configured, aza-substituted amino acid building block supplied as a Boc-protected derivative, with an additional CHA component indicated by the product naming convention. This protected amino acid form is designed for controlled incorporation into peptide and peptidomimetic synthesis workflows, where the Boc group provides compatibility with standard amino-protection strategies and the aza functionality enables downstream structural diversification. Researchers commonly select this type of protected, stereodefined aza amino acid intermediate when building non-natural backbones, conformationally distinct peptide analogs, or medicinal-chemistry fragments that require reliable handling and defined stereochemistry.
1. Peptidomimetic Building Blocks
Boc-D-Aza-OH*CHA is used by peptide and peptidomimetic development groups to assemble D-configured, aza-containing segments that are not accessible through standard proteinogenic amino acids. In custom peptide synthesis and medicinal chemistry programs, the Boc-protected amino functionality supports stepwise coupling strategies for generating non-natural peptide analogs used in structure-activity relationship studies. The aza substitution provides a distinct backbone or side-chain electronic/steric profile that can be leveraged to probe binding-site tolerance and to tune physicochemical properties during lead optimization.
2. Pharmaceutical Intermediate Synthesis
Boc-D-Aza-OH*CHA is frequently positioned as a chiral amino acid intermediate for downstream synthesis of aza-bearing fragments used in pharmaceutical intermediate development. Process and synthetic chemistry teams employ this type of protected building block to construct stereochemically defined units that later serve as precursors for larger heterocycle-containing scaffolds or constrained peptidomimetic motifs. The defined D-stereochemistry and protected amine help maintain control over chemoselectivity during multi-step assembly, which is particularly valuable when preparing libraries of analogs for screening campaigns.
3. Non-Natural Peptide Segment Assembly
Boc-D-Aza-OH*CHA supports the preparation of non-natural peptide segments where a protected D-aza amino acid is required to introduce a specific stereochemical element into an assembled sequence. Peptide manufacturing and research laboratories use this building block to generate modified peptide libraries, including analogs intended for biochemical characterization where backbone modifications are used to study structure, stability, or interaction patterns. The Boc protection pattern enables consistent handling during iterative coupling and purification workflows typical of custom peptide synthesis, helping ensure that the aza-containing residue is introduced as a defined, protected intermediate rather than as a reactive free amino acid.
4. Analytical Reference Fragment Preparation
Boc-D-Aza-OH*CHA is also used in analytical method development and reference-material preparation when aza-containing, D-configured peptide fragments are required as standards or calibration components. Analytical chemists preparing LC-MS or method-development samples rely on protected, stereodefined intermediates to generate reproducible fragment standards that reflect the exact chemical identity used in downstream synthesis. This is particularly relevant for laboratories building workflows to monitor incorporation of non-natural residues into larger peptidomimetic constructs, where consistent starting material identity improves traceability between synthesis batches and analytical readouts.
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