Boc-D-Orn-OH is a protected amino acid derivative of ornithine, featuring an N-terminal Boc (tert-butoxycarbonyl) carbamate that masks the amino functionality while retaining the amino acid backbone with a free carboxylic acid. The side chain is a straight-chain aliphatic segment ending in a primary amine, and the "D" designation indicates the D stereochemical configuration at the α-carbon. This molecule is used as a stepwise building block in peptide synthesis workflows where chemoselective coupling of the free carboxyl group and controlled handling of the protected α-amino group support the preparation of ornithine-containing peptide and amino-acid-derived structures.
CAT No: CP25414
CAS No:159877-12-0
Synonyms/Alias:159877-12-0;(R)-5-Amino-2-((tert-butoxycarbonyl)amino)pentanoicacid;BOC-D-ORN-OH;(R)-5-amino-2-(tert-butoxycarbonylamino)pentanoicacid;Boc-D-Ornithine;AmbotzBAA1185;PubChem20975;SCHEMBL205184;AMPVNPYPOOQUJF-SSDOTTSWSA-N;MolPort-008-267-394;ZINC2560689;AJ-40624;AK119671;KB-210226;Y0538;K-5012
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-ornithine
Boc-D-Orn-OH is a protected D-ornithine building block featuring a Boc-protected alpha-amino group and a free side-chain primary amine on the ornithine backbone. As a D-configured amino acid derivative, it is commonly used in peptide and peptidomimetic synthesis where stereochemical control and orthogonal functional-group availability are important. The combination of Boc protection for controlled coupling and an unprotected side-chain amine for downstream functionalization makes this reagent valuable for constructing modified peptide motifs and for preparing ornithine-derived intermediates.
1. Peptide Synthesis Building Block
Boc-D-Orn-OH is used as an amino acid building block for assembling D-ornithine-containing peptides and peptidomimetics, particularly when the side-chain needs to remain available for later derivatization. In custom peptide synthesis workflows, peptide chemists rely on the Boc-protected alpha-amino group to enable stepwise coupling while preserving the side-chain primary amine for subsequent transformations such as acylation, alkylation, or attachment of solubilizing or recognition groups. The D-configuration supports stereochemical diversification in sequence design, which is frequently leveraged in stability-focused peptide engineering and structure-activity relationship studies where stereochemistry at the residue level is a key variable.
2. Side-Chain Functionalization Intermediates
Boc-D-Orn-OH is widely used to generate ornithine-derived intermediates where the free side-chain amine serves as a handle for installing functional substituents after the protected residue has been incorporated or isolated. Medicinal chemistry and chemical biology groups use this functionality to prepare N-substituted ornithine derivatives, including amide and urea analogs, as well as linkers for attaching small molecules to peptides or other scaffolds. The Boc protection at the alpha-amino position helps maintain chemoselectivity during intermediate preparation, allowing the side-chain amine to be selectively targeted while minimizing unwanted reactions at the backbone nitrogen.
3. Peptidomimetic Linker Development
Boc-D-Orn-OH supports the development of peptidomimetic architectures that require a basic, primary-amine-containing side chain for tuning charge, solubility, and conjugation chemistry. In research programs that build modular peptide-like compounds, the reagent's free side-chain amine enables straightforward incorporation into linker strategies for attaching payloads, affinity tags, or solubilizing groups without requiring additional side-chain introduction steps. This makes Boc-D-Orn-OH a practical choice for designing D-ornithine motifs within larger synthetic sequences, where controlling the position and availability of the primary amine is essential for reliable downstream assembly and purification.
4. Pharmaceutical Intermediate Synthesis
Boc-D-Orn-OH is used as a protected amino acid intermediate in the synthesis of ornithine-related chemical entities for pharmaceutical intermediate development. Process and development chemists value the Boc-protected alpha-amino group for managing reactivity during multi-step sequences, while the side-chain primary amine provides a direct site for conversion into more stable or protected forms needed for further elaboration. This combination aligns with workflows that require a stereochemically defined ornithine derivative as a starting point for generating N-functionalized intermediates used in the construction of larger molecules, including amine-bearing fragments and backbone-modified building blocks.
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