Boc-D-Orn(Z)-OH is a protected, non-natural amino acid derivative of ornithine in which the α-amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the side-chain terminal amine is protected as a benzyloxycarbonyl (Z/Cbz-type) carbamate. The molecule contains both an α-carboxylic acid functional group and two protected nitrogen sites, with the D designation indicating the stereochemical configuration at the α-carbon center as specified by the product name. In peptide chemistry, this orthogonally protected ornithine analogue is used as a protected amino acid building block that supports stepwise coupling while suppressing undesired side reactions from the unprotected amino functionalities during synthesis and subsequent deprotection workflows.
CAT No: CP26485
CAS No:16937-92-1
Synonyms/Alias:Boc-D-Orn(Z)-OH;16937-92-1;(R)-5-(((Benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanoicacid;N-Boc-N'-Cbz-D-Ornithine;Nalpha-Boc-Ndelta-Z-D-ornithine;Ndelta-Z-Nalpha-Boc-D-ornithine;AC1OJOQD;KSC918O2R;15193_ALDRICH;N|A-Boc-N|A-Z-D-ornithine;N|A-Z-N|A-Boc-D-ornithine;SCHEMBL2369249;15193_FLUKA;CTK8B8728;MolPort-003-926-699;ZINC4534254;ANW-61132;CB-906;AN-7820;RTR-007395;AJ-51588;AK-60112;KB-210211;FT-0659940;ST24035499
Boc-D-Orn(Z)-OH is a protected D-ornithine derivative designed for peptide and peptidomimetic assembly, featuring a Boc-protected alpha-amino group and a side-chain Z (benzyloxycarbonyl) protection on the ornithine functionality. This stereochemically defined, orthogonally protected amino acid building block supports controlled incorporation of an ornithine residue into longer sequences while minimizing side reactions during coupling and deprotection steps. Its protected guanidino-equivalent side-chain functionality makes it particularly useful for constructing polycationic or highly functionalized peptide segments in solid- or solution-phase workflows.
1. Solid-Phase Peptide Synthesis
Boc-D-Orn(Z)-OH is used by peptide synthesis groups to introduce a D-Ornithine residue into protected peptide sequences where the side-chain must remain masked through repeated coupling cycles. The Boc group on the alpha-amino terminus and the Z protection on the side-chain enable sequential deprotection and coupling strategies, supporting the preparation of D-amino-acid-containing peptides for structure-function studies and chemical biology tool development. Researchers commonly select this building block when they need a defined D-configuration and a protected ornithine side-chain to reduce uncontrolled side reactions during automated or manual peptide assembly.
2. D-Amino Acid Peptide Libraries
Boc-D-Orn(Z)-OH supports peptide library construction in medicinal chemistry and protein engineering research by providing a stereochemically defined ornithine unit that can be incorporated into diverse analogs. The protected format is valuable for generating series of peptidomimetics and sequence variants where the D-ornithine position is systematically varied to probe conformational effects, backbone stereochemistry, and sequence-dependent properties. By keeping both the alpha-amino and side-chain functionalities protected during synthesis, this building block helps maintain consistency across library members and simplifies downstream purification and characterization workflows.
3. Pharmaceutical Intermediate Building Block
Boc-D-Orn(Z)-OH is also used as a pharmaceutical intermediate in the synthesis of ornithine-derived peptidomimetic fragments and protected amino acid intermediates for downstream coupling chemistry. Process and development chemists rely on the protected, isolable amino acid form to manage functional-group compatibility in multi-step routes, particularly when the target structure requires controlled unveiling of the ornithine functionality at a later stage. This makes the compound relevant to custom intermediate development where robust handling during scale-up and predictable deprotection sequencing are important for manufacturing-ready synthetic planning.
4. Protected Ornithine Segment Synthesis
Boc-D-Orn(Z)-OH is applied for the preparation of ornithine-containing peptide segments and protected oligomer fragments used in convergent assembly strategies. Peptide chemists often choose this derivative when they need to build a defined, protected D-ornithine motif that can later be condensed with other peptide segments under conditions that preserve sensitive functionalities elsewhere in the molecule. The dual protection pattern supports compatibility with fragment coupling workflows by keeping the reactive amine functionality restrained until the intended stage of synthesis, enabling more reliable construction of complex, highly functionalized peptide architectures.
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