N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt

N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt is a D-ornithine-based, orthogonally protected diamino acid derivative featuring an Nα-allyloxycarbonyl (Alloc) protecting group and an Nδ-Boc protecting group, together with a free side-chain carboxyl functionality and a salt-forming dicyclohexylamine counterion. The compound contains a defined stereocenter at the D-ornithine backbone, enabling stereochemically controlled incorporation into peptide and peptidomimetic scaffolds. Orthogonal protection of the two amino sites supports stepwise deprotection and selective functionalization, while the Alloc and Boc groups provide predictable reactivity under standard peptide-protection strategies. The salt form can improve handling and downstream coupling readiness in synthetic workflows that require stable, isolable amino acid intermediates for fine chemical synthesis and research-grade building block preparation.

1. Orthogonal Peptide Coupling

N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt is applied in peptide synthesis workflows where orthogonally protected diamino acid building blocks enable controlled Nα- and Nδ-functionalization sequences. The Alloc group on the α-amino site and the Boc group on the δ-amino site allow selective deprotection and subsequent peptide coupling chemistry that distinguishes terminal versus internal nitrogen reactivity. The D-ornithine backbone provides a stereodefined scaffold for constructing peptide bonds with predictable side-chain positioning, while the carboxyl functionality participates in standard amide-forming transformations. The resulting protected ornithine derivatives can be used to assemble multi-nitrogen peptide segments and to generate peptide analogs with controlled regiochemistry at the side-chain amino positions.

2. Peptidomimetic Side-Chain Engineering

N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt supports peptidomimetic construction and side-chain functionalization strategies that exploit the protected diamine architecture. The orthogonal nitrogen protection pattern enables sequential conversion of one amino site into conjugation handles while the other remains masked during scaffold assembly. The δ-amino functionality, protected as Boc, can be selectively revealed for downstream derivatization such as amide formation, urea/thiourea generation, or attachment of heteroaryl fragments, while the Alloc-protected α-amino site can be managed via orthogonal deprotection logic. The stereodefined D-ornithine framework can then be incorporated into molecular designs used for structure-activity relationship studies and for creating constrained analogs that probe binding-site interactions.

3. Chemical Biology Conjugation Handles

N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt is suitable for chemical biology research requiring amino acid-derived conjugation handles with controlled chemoselectivity. The presence of two protected amino sites supports staged unveiling of reactive nitrogens, enabling attachment of labels, affinity tags, or reactive moieties without uncontrolled cross-reactivity during biomolecule modification. The carboxyl group can be converted into activated intermediates for coupling to amine-bearing biomolecules or to engineered linkers, while the orthogonal protecting groups help maintain compatibility with labeling chemistries that tolerate amide-forming steps. The D-configuration can be leveraged to modulate conformational preferences in labeled peptides or protein-interaction probes, supporting downstream experiments that map molecular recognition features.

4. Pharmaceutical Intermediate Preparation

N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt can be used as a manufacturing-oriented intermediate for the preparation of protected ornithine derivatives entering peptide-like active ingredient synthesis. The orthogonal Alloc/Boc protection strategy aligns with process chemistry needs for predictable protection-deprotection cycles and for isolable intermediates that minimize nitrogen scrambling during scale-up. The salt-forming dicyclohexylamine counterion can improve crystallinity and handling characteristics in synthetic sequences where amino acid salts are preferred feed forms. The compound's defined functional group set supports downstream conversion into coupling-ready building blocks for constructing amide-rich intermediates used in fine chemical production and pharmaceutical intermediate generation.

5. Solid-Phase Building Block Use

N-α-Allyloxycarbonyl-N-δ-Boc-D-ornithine dicyclohexylamine salt is compatible with solid-phase peptide synthesis and related stepwise assembly methods that benefit from orthogonal protecting groups. The Alloc and Boc groups provide a protection pattern that can be selectively removed to expose one nitrogen at a time, supporting controlled sequential coupling and minimizing side reactions from the diamino side chain. The D-ornithine stereocenter contributes to reproducible spatial arrangement of the side-chain amines within the growing peptide chain, which is relevant for generating defined peptide architectures and for producing stereochemically consistent analog libraries. The compound can function as a protected amino acid building block for constructing multi-amino segments and for producing ornithine-containing peptides used in analytical reference preparation and method development.

1. Zeta-potential-changing nanoparticles conjugated with cell-penetrating peptides for enhanced transfection efficiency

2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate

3. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die

4. Investigating Potential Interactions Between Neurohypophyseal Peptides, their Drug Analogs, and Coagulation Factor VIII

5. The effect of B-type allatostatin neuropeptides on crosstalk between the insect immune response and cold tolerance