Boc-D-Arg-OH*H2O*HCl is a protected, stereodefined amino acid derivative of arginine in which the α-amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the compound is present as a hydrate and hydrochloride salt. The molecule contains a free α-carboxylic acid group and an arginine side chain bearing a guanidinium functionality, while the D stereochemical designation specifies the configuration at the chiral α-carbon. It is used as a protected building block for stepwise peptide synthesis and related conjugation workflows where Boc protection controls chemoselectivity of the amino functionality and the guanidinium side chain provides a strongly basic, hydrogen-bonding handle for incorporation into larger peptide and amino acid frameworks.
CAT No: CP25171
CAS No:113712-06-4
Synonyms/Alias:N-BOC-D-Argininehydrochloride;113712-06-4;(R)-2-((tert-Butoxycarbonyl)amino)-5-guanidinopentanoicacidhydrochloride;Boc-D-Arg-OH.HCl;N-ALPHA-BOC-L-ARGININEHYDROCHLORIDE;KSC911K3L;SCHEMBL7264801;CTK8B1535;MolPort-009-198-493;Nalpha-Boc-D-arginineHydrochloride;ANW-28316;FC1231;AKOS015847167;RTR-014794;AK-75721;SC-24261;KB-209687;B2204;(tert-butoxycarbonyl)-D-argininehydrochloride;Nalpha-(tert-Butoxycarbonyl)-D-arginineHydrochloride
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-arginine monohydrat hydrochloride
Boc-D-Arg-OH*H2O*HCl is a D-configured arginine building block supplied as a hydrated hydrochloride salt, featuring the Boc protecting group on the α-amino functionality and the guanidinium side chain characteristic of arginine. This protected form is widely used in peptide chemistry where controlled, stepwise deprotection and coupling of the amino acid residue are required, while the arginine side chain is maintained in a protected, synthesis-compatible state for reliable chain assembly. The salt and hydration state support handling and weighing for laboratory and custom peptide workflows.
1. Solid-Phase Peptide Synthesis
Boc-D-Arg-OH*H2O*HCl is commonly used in solid-phase peptide synthesis workflows to introduce D-arginine residues into peptide sequences for research-grade peptide libraries and stereochemically defined analogs. Peptide synthesis teams select this protected arginine derivative to maintain the Boc-protected α-amino group during chain elongation, enabling controlled coupling cycles and subsequent deprotection steps to build the desired peptide architecture. Its arginine side-chain functionality is particularly relevant when the target peptide requires guanidinium-containing motifs for charge distribution studies, sequence-dependent behavior, or structured peptide design.
2. Stereochemical Peptide Analog Development
Boc-D-Arg-OH*H2O*HCl supports the preparation of stereochemically defined peptide analogs used in structure-activity relationship investigations and chemical biology studies that compare peptide behavior across stereochemistry. Researchers incorporate D-arginine residues to probe how backbone stereochemistry influences peptide conformation, stability in chemical or enzymatic contexts, and interaction patterns in assay systems. In these workflows, the protected amino acid form is selected to ensure consistent residue incorporation during custom peptide synthesis, yielding peptides with well-defined stereochemical composition for downstream characterization by HPLC, LC-MS, and NMR.
3. Pharmaceutical Intermediate Building Blocks
Boc-D-Arg-OH*H2O*HCl is also used as a protected amino acid intermediate in pharmaceutical intermediate development for constructing arginine-containing fragments and peptidomimetic scaffolds. Process and development chemists rely on Boc-protected, salt-form amino acid reagents to manage reactivity during multistep synthesis and to align with standard protecting-group strategies used for amide bond formation and fragment coupling. The D-configuration and arginine side-chain functionality make this material relevant when stereodefined syntheses are required for candidate optimization, analytical reference preparation, or route development toward larger, arginine-rich intermediates.
4. Custom Peptide Manufacturing Research
Boc-D-Arg-OH*H2O*HCl is frequently ordered by custom peptide synthesis providers and academic peptide groups to support rapid turnaround synthesis of D-amino acid-containing peptides and sequence variants. Contract synthesis teams value this reagent because it integrates directly into established peptide assembly workflows, allowing consistent incorporation of a protected D-arginine residue without requiring ad hoc modifications to the coupling strategy. For end users, the result is a reproducible synthetic route to peptides that contain stereochemically defined arginine positions for analytical method development, reference standard generation, and comparative studies across peptide series.
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