Boc-Homoarg(NO2)-OH is a Boc-protected amino acid derivative based on a homoarginine scaffold bearing a nitro-substituted guanidino side chain, positioning it within the arginine-class of amino acid building blocks used for peptide chemistry. The molecule contains a Boc-protected α-amino group and a free carboxylic acid, while the side chain presents a guanidino functionality modified with a nitro (NO2) substituent that can influence hydrogen-bonding and electronic properties relative to unmodified arginine. In synthesis, the Boc group supports chemoselective handling of the amino functionality during stepwise assembly of peptides or peptidomimetics, and the nitro-bearing side chain provides a handle for subsequent chemical transformations or for incorporation into structure-activity and labeling studies where an electronically modified guanidino mimic is required.
CAT No: CP26961
CAS No:28968-64-1
Synonyms/Alias:Boc-HomoArg(NO2)-OH;28968-64-1;(S)-2-((tert-Butoxycarbonyl)amino)-6-(3-nitroguanidino)hexanoicacid;boc-n'-nitro-l-homoarginine;PubChem18972;SCHEMBL10254700;CTK8F8305;MolPort-006-701-268;C12H23N5O6;Boc-Nomega-(nitro)-L-homoarginine;Boc-HomoArg(NO2)-OHhydrochloride;6370AH;CB-423;ZINC15721496;AKOS024259080;AK-49652;FT-0638823
Boc-Homoarg(NO2)-OH is a Boc-protected homoarginine derivative bearing a nitro-substituted side-chain, supplied as a protected amino acid building block for controlled incorporation into protected peptide segments. The Boc group enables standard amino acid coupling workflows, while the nitro functionality provides a distinct chemical handle for downstream derivatization or side-chain modification during peptide and peptidomimetic development. Researchers select this compound when they need a longer, guanidinium-like side-chain scaffold with an electronically differentiated substituent to support structure-property studies and synthetic intermediate preparation.
1. Peptide Segment Building
Boc-Homoarg(NO2)-OH is used by peptide synthesis groups to assemble protected peptide segments where a homoarginine-like residue with a nitro-functional side chain is required. The Boc-protection pattern supports stepwise coupling strategies commonly used in custom peptide manufacturing and research-grade peptide library construction, allowing the residue to be introduced as a defined unit within a larger sequence. This building block format is particularly useful when the side-chain nitro group must remain intact through assembly to enable later functional conversion or to tune the electronic character of the resulting peptide.
2. Peptidomimetic Side-Chain Engineering
Boc-Homoarg(NO2)-OH supports medicinal chemistry and chemical biology teams developing peptidomimetics and constrained analogs that incorporate an extended, guanidinium-mimicking side-chain architecture. The nitro substituent provides a chemically distinct motif that can be leveraged to create analog series for structure-activity relationship work or to generate downstream derivatives after peptide assembly. In practice, this protected amino acid derivative is valued as a reproducible intermediate that helps maintain sequence-level control while providing a modifiable side-chain handle for subsequent derivatization steps.
3. Pharmaceutical Intermediate Derivatization
Boc-Homoarg(NO2)-OH is also used as a protected amino acid intermediate in pharmaceutical intermediate development where controlled side-chain functionality is required for scalable synthesis planning. The Boc-protected backbone and preserved nitro group allow downstream conversion into other functionalized side-chain variants without disrupting the peptide-derived framework during early-stage processing. This makes the compound relevant for route development teams preparing specialized building blocks for larger synthetic programs, including the generation of functionalized guanidinium-like motifs and electronically differentiated analogs used in lead optimization workflows.
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