Boc-D-Arg(Z)2-OH is a protected amino acid derivative of D-arginine, featuring the guanidinium-containing arginine side chain and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The side-chain guanidinium is protected as a Z-type (benzyloxycarbonyl) group indicated by "(Z)2," while the molecule retains the free carboxylic acid functionality and the D stereochemical configuration specified by the product name. This compound is used as a stepwise building block in peptide synthesis workflows, where the orthogonal protection pattern supports controlled coupling chemistry for assembling arginine-containing peptide sequences and for preparing more complex amino acid derivatives.
CAT No: CP26397
CAS No:145881-13-6
Synonyms/Alias:BOC-D-ARG(Z)2-OH;145881-13-6;C27H34N4O8;6313AH;ZINC71788039;AKOS015909660;K-4666;I14-32631;Nalpha-(tert-Butoxycarbonyl)-omega,omega'-bis(benzyloxycarbonyl)-D-arginine
Boc-D-Arg(Z)2-OH is a protected D-arginine building block designed for peptide and peptidomimetic assembly, featuring a Boc-protected amino group and an arginine side chain protected as a benzyloxycarbonyl-type (Z) derivative. The D-configuration supports stereochemical control in non-native peptide designs where resistance to proteolysis and altered conformational behavior are often key development goals. Its protected guanidinium functionality and carboxylic acid enable downstream coupling strategies commonly used in research-grade synthesis workflows.
1. Stereocontrolled Peptide Synthesis
Boc-D-Arg(Z)2-OH is used by peptide chemists to incorporate a D-arginine residue at defined positions during custom peptide synthesis, including solution-phase and solid-phase workflows where orthogonal side-chain protection and controlled reactivity are required. The Boc group provides an established N-terminal protection strategy for stepwise assembly, while the protected arginine side chain prevents undesired side reactions during chain elongation. Researchers developing D-amino-acid-containing peptides, cyclic or constrained analogs, and protease-resistant peptide scaffolds rely on this type of protected building block to maintain sequence fidelity and minimize protecting-group scrambling during coupling and deprotection cycles.
2. Non-Native Residue Peptidomimetics
Boc-D-Arg(Z)2-OH supports medicinal chemistry and chemical biology programs that build peptidomimetic libraries with non-proteinogenic stereochemistry. Incorporating a D-arginine analog is a common strategy for probing structure-activity relationships, tuning charge presentation, and evaluating how stereochemical inversion impacts peptide folding and receptor/biomolecular recognition in assay systems. Development groups preparing analog series for SAR studies typically choose a protected arginine derivative to ensure reliable coupling performance and to keep the side-chain functionality masked until the target stage of synthesis, enabling consistent library generation and purification workflows.
3. Complex Segment Coupling
Boc-D-Arg(Z)2-OH is frequently selected for assembling larger peptide segments where protected arginine residues must remain chemically stable throughout multiple reaction steps. Peptide synthesis teams use this building block when preparing difficult sequences that require careful control of protecting-group compatibility, especially in late-stage fragment coupling or iterative elongation toward longer constructs. The combination of Boc protection on the alpha-amino group and side-chain protection on arginine supports reproducible intermediate handling, helping teams maintain clean reaction profiles and reduce the risk of side reactions associated with free guanidinium under peptide-manufacturing conditions.
4. Pharmaceutical Intermediate Development
Boc-D-Arg(Z)2-OH also finds use as a protected amino acid intermediate for downstream synthesis of arginine-containing intermediates used in research and industrial chemical development. Process and R&D chemists incorporate this type of protected D-arginine derivative when preparing specialized building blocks for peptide-based candidates, cyclic peptide precursors, or stereochemically defined intermediates required for further functionalization. The presence of a masked side-chain functionality and a protected amino group makes it convenient for controlled conversion into activated coupling partners or for integration into multi-step synthetic sequences where protecting-group strategy is central to yield and reproducibility.
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