Boc-D-HArg(Et)2-OH is a protected, non-natural amino acid derivative featuring the D-configured arginine backbone with two ethyl substituents on the guanidinium side chain, and it belongs to the arginine class of amino acid building blocks. The molecule contains an N-terminal Boc (tert-butoxycarbonyl) protecting group and a carboxylic acid functional group, while the side-chain guanidinium functionality is substituted with ethyl groups to alter hydrogen-bonding and basicity relative to unmodified arginine. As a Boc-protected amino acid, it is employed as a precursor for stepwise peptide synthesis and for preparing arginine-analogue peptides or conjugates where the modified, dialkylated guanidinium side chain provides a defined chemical handle for structure-function studies and analytical characterization.
CAT No: CP25156
CAS No:110761-76-7
Synonyms/Alias:(R)-2-((tert-Butoxycarbonyl)amino)-6-(1,3-diethylguanidino)hexanoicacid;110761-76-7;CTK8B9828;MolPort-023-331-668;ANW-63227;ZINC82048650;AKOS016004405;AK-87901;AJ-124787;KB-209690;TC-151972
Chemical Name:N-alpha-t-Butyloxycarbonyl-N,N-diethyl-D-homoarginine
Boc-D-HArg(Et)2-OH is a protected D-configured arginine derivative designed for peptide synthesis workflows, featuring a Boc-protected amino group and a side-chain guanidinium protected as diethyl (Et) groups to control chemoselectivity during coupling and subsequent assembly. The arginine side chain retains the characteristic guanidinium functionality in a protected form, making this building block particularly useful when robust handling of basic residues is required. This reagent is typically selected by peptide chemists and process developers who need a defined stereochemical arginine unit with protection that supports reliable stepwise synthesis.
1. Solid-Phase Peptide Synthesis
Boc-D-HArg(Et)2-OH is used as an arginine building block in solid-phase peptide synthesis where incorporation of a D-arginine residue is required for peptide stability studies, protease resistance evaluation, or stereochemical control in peptide design. The Boc group provides compatibility with standard stepwise deprotection and coupling cycles, while the diethyl-protected guanidinium helps prevent side reactions associated with strongly basic side chains during chain elongation. Researchers preparing D-arginine-containing peptides for chemical biology and peptide library work often choose this specific protected form to maintain high fidelity of sequence assembly and to simplify downstream handling of the basic side chain.
2. D-Arginine Peptide Library Building
Boc-D-HArg(Et)2-OH supports the synthesis of structured peptide libraries and stereochemically defined analog series where replacing L-arginine with D-arginine is used as a design variable. In practice, peptide discovery and SAR-oriented studies benefit from having a consistent, protected D-arginine unit that can be introduced at defined positions using routine peptide coupling strategies. The Et2-protected guanidinium form is particularly helpful for maintaining side-chain integrity across multiple synthesis steps, enabling parallel preparation of peptides that differ in stereochemistry while keeping the rest of the backbone chemistry comparable for analytical characterization.
3. Pharmaceutical Intermediate Development
Boc-D-HArg(Et)2-OH is also employed as a protected amino acid intermediate in the manufacture of peptide-based drug candidates and peptide fragments where stereochemically defined arginine residues are required for final active or advanced intermediates. Process development teams and custom synthesis providers rely on protected, well-defined building blocks to reduce variability during scale-up and to manage the reactivity of basic side chains under controlled conditions. By using a Boc-protected, diethyl-guanidinium-protected D-arginine derivative, downstream assembly of larger peptide intermediates can be performed with improved operational consistency, supporting the production of defined stereochemical sequences for further development.
4. Analytical Reference Peptide Preparation
Boc-D-HArg(Et)2-OH is used to prepare defined D-arginine-containing peptide standards and reference materials for method development and characterization workflows. Analytical laboratories preparing LC-MS/MS or HPLC reference peptides often require stereochemically unambiguous sequences to validate retention behavior, fragmentation patterns, and identity assignments, especially when D-amino acid substitutions are part of the study design. The protected arginine building block enables reproducible synthesis of these reference peptides with controlled side-chain protection during assembly, supporting reliable downstream deprotection and purification to yield well-defined analytical targets.
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