Boc-D-Arg(Pbf)-OH is a protected amino acid derivative based on D-arginine bearing a guanidinium side chain, where the amino acid backbone is protected as the Boc carbamate and the arginine side chain is protected as a Pbf (2,2,4,6,7-pentamethyl-dihydrobenzofuran) ether-like protecting group. The molecule contains a Boc-protected α-amino group and a carboxylic acid functionality while the guanidinium functionality is masked by the Pbf group, and the stereochemical form is indicated as D by the product name. In peptide synthesis workflows, this protected analogue is used as a stepwise building block to control chemoselectivity by preventing unwanted side reactions of the guanidinium during coupling and deprotection steps, and it is also employed in structure-activity studies and analytical preparations where arginine side-chain protection is required.
CAT No: CP25499
CAS No:186698-61-3
Synonyms/Alias:Boc-D-Arg(Pbf)-OH;186698-61-3;Boc-Nw-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine;C24H38N4O7S;Nalpha-Fmoc-Nomega-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine;AmbotzBAA1021;47348_ALDRICH;47348_FLUKA;CTK8F0143;ZINC15721600;AKOS025289352;AK170037;RT-011789;FT-0660780;FT-0696161;X5184
Chemical Name:N-alpha-(t-Butyloxycarbonyl)-N-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-D-arginine
Boc-D-Arg(Pbf)-OH is a protected D-configuration arginine building block designed for peptide synthesis, featuring a Boc-protected alpha-amino group and a Pbf-protected guanidinium side chain to control reactivity during coupling and deprotection steps. This reagent is widely used when a D-arginine residue is required for stereochemical control, conformational effects, or protease-stability studies, while the Pbf group helps suppress side-chain side reactions under standard peptide assembly conditions.
1. D-Arginine Peptide Synthesis
Boc-D-Arg(Pbf)-OH is used by peptide chemists to introduce a D-arginine residue into peptide sequences where stereochemistry is a key design element, such as D-amino acid-enriched peptides and stereochemically defined analogs. The Boc group supports common protected-amino-acid coupling workflows, while the Pbf-protected guanidinium side chain maintains the strongly basic functionality in a protected, non-interfering state during chain assembly. Researchers developing cyclic peptides, cell-penetrating peptide variants, or protease-challenge constructs often select this specific protection pattern to minimize guanidinium-related complications during synthesis and purification.
2. Complex Segment Coupling
Boc-D-Arg(Pbf)-OH is frequently selected for assembling longer or more complex peptide segments that require reliable side-chain protection to preserve sequence integrity across multiple coupling and deprotection cycles. The Pbf protection on the arginine side chain is particularly helpful when neighboring residues include nucleophilic or base-sensitive functionalities, because it reduces the likelihood of unwanted side reactions from the guanidinium group during iterative synthesis. This makes the reagent a practical choice for custom peptide manufacturing research where reproducibility across multiple batches and consistent incorporation of D-Arg residues are required.
3. Peptidomimetic and SAR Studies
Boc-D-Arg(Pbf)-OH supports medicinal chemistry and chemical biology programs that build peptidomimetics and structure-activity relationship (SAR) libraries containing D-arginine substitutions. By enabling site-specific placement of a D-Arg unit, the reagent helps teams probe how stereochemical inversion at a cationic residue influences peptide conformation, binding-site geometry, and overall sequence behavior in downstream assays. The protected guanidinium functionality is also advantageous for library synthesis workflows that demand orthogonal handling of side-chain reactivity while maintaining the arginine charge motif in the final peptide.
4. Orthogonally Protected Intermediate Access
Boc-D-Arg(Pbf)-OH is used as a defined, protected amino acid intermediate for preparing arginine-containing peptide fragments and advanced coupling-ready building blocks in research-grade synthesis pipelines. The combination of Boc on the alpha-amino group and Pbf on the guanidinium side chain provides a controlled reactivity profile that aligns with standard peptide assembly logic, helping chemists manage deprotection and coupling order when building fragments with multiple protected residues. This approach is commonly adopted in laboratories that generate intermediate peptides for later functionalization, including downstream conjugation steps that require the arginine side chain to be handled predictably during synthesis.
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