N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt is a protected, amino acid derivative of L-ornithine featuring an N-allyloxycarbonyl (Alloc) group at the α-amino position and an N-Boc group at the δ-amino side-chain position, with the remaining carboxyl group present as part of a salt form. The molecule contains both an α-carboxyl functional group and two nitrogen atoms bearing orthogonally removable protecting groups, where the Alloc and Boc groups control chemoselectivity by suppressing undesired amine reactivity during stepwise assembly of peptide or peptidomimetic structures. As a dicyclohexylamine salt, it is commonly used as a protected building block in synthetic peptide chemistry and related chemical biology workflows that require orthogonal deprotection of the α- and δ-amino functionalities for controlled incorporation into more complex amino acid and peptide derivatives.
CAT No: CP08704
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt is an L-ornithine-derived amino acid salt bearing two orthogonally removable protecting groups: an N-α allyloxycarbonyl (Alloc) group and an N-δ Boc group on the side-chain terminal amine. The molecule contains a stereogenic α-carbon consistent with L-configuration, a protected α-amino functionality, and a protected δ-amino functionality that can participate in selective peptide coupling after deprotection. The dicyclohexylamine salt form improves handling and can influence crystallization behavior during protected amino acid synthesis and downstream intermediate preparation. The presence of Alloc and Boc chemistries enables controlled orthogonal deprotection sequences, while the remaining carboxyl group is positioned for conversion into activated derivatives used in peptide building block workflows.
1. Peptide Synthesis
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt supports peptide building block preparation for segments containing protected ornithine residues, where orthogonal N-protection is required to control which nitrogen participates in coupling. Alloc on the α-nitrogen and Boc on the δ-nitrogen provide a protection strategy compatible with stepwise N-deprotection, enabling sequential formation of amide bonds at distinct positions. The protected amines can be converted into coupling-ready forms after selective removal of Alloc under conditions that preserve Boc, allowing controlled incorporation into linear peptides and protected peptide fragments. The resulting ornithine-containing peptides can be used as research-grade intermediates for structure-activity relationship studies and for generating peptidomimetic scaffolds with defined side-chain functionality.
2. Side-Chain Functionalization
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt is suitable for side-chain functionalization workflows that rely on the orthogonality of Alloc and Boc to expose one amine while keeping the other masked. The δ-amino group, protected as Boc, can be selectively deprotected to generate a nucleophilic handle for subsequent derivatization such as acylation, sulfonylation, or attachment of linkers used in peptide conjugation chemistry. Alloc removal can expose the α-amino site for controlled coupling or for installing additional substituents without uncontrolled cross-reactivity at the side-chain amine. Downstream derivatives prepared from this protected ornithine salt can serve as intermediates for chemical biology probes, linker-bearing peptide analogs, and functionalized amino acid derivatives used in synthetic organic chemistry.
3. Chemical Biology Probes
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt can be applied in chemical biology research where ornithine-based motifs are incorporated into labeled or affinity-tagged constructs. The protected α- and δ-amines enable stepwise assembly of peptide or peptidomimetic backbones, allowing attachment of fluorophores, biotin-like handles, or other recognition elements through amide or amine coupling after orthogonal deprotection. The L-configuration and defined side-chain amine positioning support consistent stereochemical outcomes in molecular recognition studies, including fragment screening libraries built from amino acid-derived scaffolds. The salt form and orthogonal protecting groups facilitate reproducible intermediate handling when generating probe candidates and their downstream conjugation products.
4. Peptidomimetics And SAR
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt is suitable for peptidomimetic construction and structure-activity relationship studies that require ornithine-like spacing and controlled functional group placement. Alloc/Boc orthoprotection supports selective introduction of substituents at either the α-amino position or the δ-side-chain amine, enabling systematic variation of linker length, charge distribution, and hydrogen-bonding patterns across analog series. The protected carboxyl functionality aligns with peptide coupling chemistry used to generate amide-linked scaffolds that can be further transformed into constrained or substituted analogs. The resulting ornithine-containing intermediates can be employed to build SAR-focused libraries, generate reference standards for analytical evaluation, and support iterative medicinal chemistry synthesis around amino acid-derived motifs.
5. Pharmaceutical Intermediate Preparation
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt is relevant to pharmaceutical intermediate preparation where orthogonally protected amino acid derivatives are used to control impurity formation during multi-step assembly. The Alloc group provides a chemically distinct deprotection handle relative to Boc, enabling manufacturing route design that separates protection removal steps and reduces the risk of premature exposure of both nitrogens. The dicyclohexylamine salt form can be leveraged for improved physical handling during scale-up of protected amino acid intermediates, supporting downstream conversion into activated coupling derivatives used in peptide-like synthesis. The compound's defined stereochemistry and protected functional groups make it suitable for producing ornithine-based intermediates that feed into fine chemical synthesis and controlled synthesis of complex nitrogen-rich building blocks.
6. Process Chemistry And Fine Chemical Synthesis
N-α-Allyloxycarbonyl-N-δ-Boc-L-ornithine dicyclohexylamine salt can be employed in process chemistry for producing nitrogen-functionalized chiral intermediates with predictable protection-group behavior. The combination of Alloc and Boc enables orthogonal protection/deprotection sequences that can be integrated into stepwise manufacturing operations, including selective activation of the carboxyl group for amide bond formation while maintaining one nitrogen protected. The side-chain terminal amine protection supports controlled derivatization without uncontrolled oligomerization, which is particularly relevant for industrial fine chemical synthesis of amino acid derivatives and peptide intermediates. The salt form and robust protecting-group framework support scalable preparation of ornithine-containing building blocks used across chemical manufacturing and applied amino acid chemistry workflows.
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