N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine is a protected, non-natural amino acid derivative of ornithine in which the α-amino group is carbamated with a Boc group and the δ-amino group on the side chain is masked as an allyloxycarbonyl (Alloc) carbamate. The molecule contains a free carboxyl group and a D-stereocenter as indicated by the product name, while the remaining functionalities are the two orthogonally protected amines that control chemoselectivity during stepwise coupling chemistry. In peptide and amino acid derivative synthesis, this orthogonally protected ornithine analogue functions as a precursor for constructing side-chain functionalized peptide motifs and for generating selectively deprotected intermediates for further derivatization or conjugation workflows.
CAT No: CP08706
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine is a D-configured ornithine derivative bearing two orthogonal nitrogen-protecting groups: an α-amino Boc carbamate and a δ-side-chain allyloxycarbonyl (Alloc) carbamate. The molecule retains the free carboxylate functionality as an amino acid backbone handle for peptide coupling, while the protected side-chain amine is masked as an Alloc carbamate that can be selectively removed under mild conditions. The presence of a stereogenic center at the ornithine α-carbon provides defined chiral recognition in downstream peptide synthesis and chiral intermediate preparation. The combination of Boc and Alloc protection supports controlled deprotection sequencing, enabling selective functionalization at the δ-position for side-chain modification, peptidomimetic construction, and process-compatible intermediate generation.
1. Peptide Synthesis
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine is applied as a protected amino acid building block for stepwise peptide assembly where orthogonal N-protection is required for selective coupling and later side-chain elaboration. The Boc-protected α-amino group supports standard peptide coupling chemistry to form amide bonds at the N-terminus, while the δ-Alloc carbamate masks the side-chain amine to prevent undesired branching or crosslinking during chain elongation. Selective Alloc deprotection enables subsequent δ-functionalization, including conversion to free ornithine side-chain amines or derivatization into side-chain constrained motifs. The D-configuration can be incorporated into peptides to probe stereochemical effects on folding, receptor recognition, or enzymatic processing, supporting structure-activity relationship studies and peptide analog generation.
2. Side-Chain Functionalization
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine serves in amino acid modification workflows that target the δ-amine for controlled functional group installation without disturbing the α-amide-forming site. The Alloc group provides a chemically addressable protecting strategy for orthogonal deprotection, allowing δ-position activation after peptide coupling or intermediate assembly. The δ-amine can be liberated to enable formation of urea, sulfonamide, carbamate, or acylated derivatives, supporting downstream synthesis of polyamine mimetics and ornithine-derived scaffolds. The resulting functionalized products can be used to generate libraries for chemical biology research and to prepare defined, stereochemically controlled intermediates for fine chemical synthesis.
3. Protected Amino Acid Chemistry
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine is suitable for protected amino acid synthesis and protecting-group strategy development in chiral building block manufacturing. The Boc carbamate and Alloc carbamate represent an orthogonal protection pair that can be sequenced to expose either the α-amino functionality or the δ-side-chain amine as required by the synthetic plan. The stable carbamate frameworks support handling through coupling and purification steps, while the Alloc handle enables selective transformations that reduce protection scrambling in multi-step routes. Defined D-stereochemistry makes the compound a practical chiral intermediate for producing ornithine-containing peptide fragments, peptidomimetic backbones, and stereochemically defined research reagents.
4. Chemical Biology Conjugation
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine can be used to prepare amino acid-derived handles for chemical biology workflows that require controlled attachment points on polyamine-like motifs. The δ-amine, once unmasked from the Alloc carbamate, can participate in conjugation chemistries that connect biomolecule-reactive moieties such as activated esters, isothiocyanates, or electrophilic acylating agents. The Boc-protected α-amino group supports incorporation into peptide linkers that maintain defined spacing and orientation of the conjugation site. D-ornithine incorporation can further modulate recognition and stability of resulting conjugates, enabling reagent construction for biomolecule labeling, affinity probe development, and mechanistic studies of amino acid-containing linkers.
5. Pharmaceutical Intermediate Preparation
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine is relevant to pharmaceutical intermediate preparation where ornithine-based fragments are used to build peptide-like or polyamine-containing structures. The protected α-amino group and carboxyl functionality enable conversion into coupling-ready intermediates that can be assembled into larger synthetic sequences for peptidomimetic or constrained peptide scaffolds. Orthogonal Boc/Alloc protection supports scalable route design by allowing selective exposure of the δ-amine for late-stage functionalization, reducing the number of protection-deprotection cycles. The compound's chiral amino acid framework supports the preparation of stereodefined intermediates used in medicinal chemistry campaigns and in manufacturing-oriented fine chemical synthesis of ornithine-containing building blocks.
6. Process Chemistry Intermediate
N-α-Boc-N-δ-allyloxycarbonyl-D-ornithine is applicable to process chemistry intermediate development where reproducible protection management and selective deprotection are central to route robustness. The dual nitrogen protection pattern allows chemoselective transformations aligned with manufacturing sequences: Boc can protect the α-amino site during coupling operations, while Alloc can be used as a controlled handle for δ-functionalization at a chosen stage. The amino acid backbone supports downstream conversion into activated derivatives for peptide coupling or for incorporation into longer-chain intermediates used in industrial peptide and peptidomimetic production. The stereochemically defined D-ornithine core supports consistent material generation for research-grade and production-scale synthesis of chiral amino acid derivatives and peptide building blocks.
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