Boc-Arg(Mbs)-OH is a protected arginine amino acid derivative in which the α-amino group is masked by a Boc (tert-butoxycarbonyl) protecting group and the side-chain guanidinium functionality is substituted with an Mbs (mesitylenesulfonyl) protecting group. The molecule contains a free carboxylic acid and a protected guanidinium side chain, with the Boc group and Mbs group together controlling chemoselectivity during peptide-coupling steps by suppressing undesired amine and guanidinium reactivity. It is used as a building block for stepwise peptide synthesis and for preparing arginine-containing peptide intermediates where selective deprotection and controlled side-chain reactivity are required for further functionalization or incorporation into larger peptide structures.
CAT No: CP27241
CAS No:58810-09-6
Synonyms/Alias:5874-75-9;H-Orn(Z)-OMe?HCl;H-ORN(Z)-OMEHCL;H-Orn(Z)-OMe.HCl;C14H20N2O4.HCl;SCHEMBL6624995;MolPort-020-004-754;ZUJMKNWYEVTCNT-YDALLXLXSA-N;KM0236;AKOS025289394;AK170120;FT-0686510;V6783;N-Delta-Z-L-Ornithinemethylesterhydrochloride;Methyl(2S)-2-amino-5-benzyloxycarbonylaminopentanoatehydrochloride;L-Ornithine,N5-[(phenylmethoxy)carbonyl]-,methylester,hydrochloride(1:1)
Boc-Arg(Mbs)-OH is a protected arginine amino acid building block featuring an N-terminal Boc (tert-butoxycarbonyl) protecting group and an Mbs (2-methylbenzenesulfonyl) side-chain protection on the guanidinium functionality. This protection pattern is commonly used to control side-chain reactivity during peptide assembly, enabling reliable incorporation of arginine residues into peptide sequences. The product is supplied as a synthetic intermediate intended for stepwise peptide synthesis workflows where orthogonal protection and clean deprotection/activation steps are critical for downstream coupling and final peptide handling.
1. Solid-Phase Peptide Synthesis
Boc-Arg(Mbs)-OH is used by peptide synthesis groups to introduce arginine residues into peptide chains during solid-phase peptide synthesis, where the Boc group protects the α-amino functionality and the Mbs group suppresses guanidinium side-chain reactivity. Researchers typically select this building block when they need robust side-chain protection compatible with standard peptide assembly conditions, helping minimize undesired side reactions that can occur with unprotected arginine. The resulting arginine-containing peptide intermediates are routinely advanced through further coupling cycles to generate arginine-rich sequences used in structure-activity relationship studies, peptide library construction, and sequence optimization campaigns.
2. Peptide Segment Coupling
Boc-Arg(Mbs)-OH is also applied in solution-phase workflows for preparing peptide segments that include arginine at defined positions, including fragment condensation where side-chain control is essential. In custom peptide manufacturing and medicinal chemistry support labs, this protected arginine is used to build longer constructs by coupling pre-formed fragments while maintaining the guanidinium group in a protected state until the desired stage of the synthesis. The Boc/Mbs protection scheme supports downstream processing of the assembled intermediates, making the reagent practical for developing arginine-containing peptide leads, stapled or modified peptide analogs, and other sequence-defined peptide materials where the integrity of the arginine side chain must be preserved during assembly.
3. Pharmaceutical Intermediate Development
Boc-Arg(Mbs)-OH serves as a key protected amino acid intermediate for producing arginine-containing peptide building blocks used in pharmaceutical intermediate development and specialty chemical manufacturing. Medicinal chemistry teams and CDMO process development groups often rely on protected arginine derivatives to standardize intermediate quality and to manage reactivity throughout multi-step synthesis, especially when guanidinium functionality must be masked during coupling and purification. This reagent is therefore commonly incorporated into internal intermediate catalogs for producing protected peptide fragments, reference materials for process characterization, and sequence-specific intermediates that later undergo controlled deprotection to yield the target peptide or peptidomimetic precursor.
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