CAT No: CP26267
CAS No:125602-26-8
Synonyms/Alias:125602-26-8;Boc-N-Me-Arg(Mtr)-OH;(S)-2-((tert-Butoxycarbonyl)(methyl)amino)-5-(3-((4-methoxy-2,3,6-trimethylphenyl)sulfonyl)guanidino)pentanoic acid;Boc-Nalpha-Me-Arg(Mtr)-OH;(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid;L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]methyl]-N2-methyl-;Boc-Nalpha-methyl-Nomega-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-L-arginine;MFCD00236863;DTXSID70672930;AKOS015909627;S-125602-26-8;(2S)-2-[(TERT-BUTOXYCARBONYL)(METHYL)AMINO]-5-[N'-(4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL)CARBAMIMIDAMIDO]PENTANOIC ACID;(E)-N~5~-{Amino[(4-methoxy-2,3,6-trimethylbenzene-1-sulfonyl)amino]methylidene}-N~2~-(tert-butoxycarbonyl)-N~2~-methyl-L-ornithine;L-Ornithine,n2-[(1,1-dimethylethoxy)carbonyl]-n5-[imino[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]methyl]-n2-methyl-;N2-(tert-Butoxycarbonyl)-Nw-((4-methoxy-2,3,6-trimethylphenyl)sulfonyl)-N2-methyl-L-arginine;
Boc-N-Me-Arg(Mtr)-OH is a Boc-protected, N-methylated arginine building block bearing an Mtr (4-methoxy-2,3,6-trimethylbenzenesulfonyl) side-chain protecting group, designed for controlled incorporation of a sterically tuned Arg residue during peptide assembly. The combination of N-methylation and robust guanidinium side-chain protection supports the preparation of peptides and peptidomimetics where reduced backbone hydrogen-bonding and minimized side reactions are important for downstream coupling and purification workflows. This reagent is commonly used by peptide synthesis groups to generate Arg-containing sequences with defined stereochemical and functional-group integrity through standard protected-amino-acid condensation strategies.
1. Solid-Phase Peptide Assembly
Boc-N-Me-Arg(Mtr)-OH is used in solid-phase peptide synthesis workflows to introduce a protected, N-methylated arginine residue at specific positions within peptide sequences. Peptide chemists rely on the Boc group for N-terminal protection during chain growth, while the Mtr-protected guanidinium side chain provides strong suppression of arginine side reactions under typical coupling and deprotection conditions. The N-methyl substitution is particularly valuable when researchers aim to modulate backbone conformation and hydrogen-bonding patterns in peptide libraries, including sequence variants used for structure-activity relationship studies and peptide optimization campaigns.
2. Peptidomimetic and SAR Libraries
Boc-N-Me-Arg(Mtr)-OH supports medicinal chemistry and chemical biology programs that build peptidomimetic scaffolds containing constrained or backbone-modified arginine analogs. By providing a protected arginine guanidinium in a form compatible with stepwise assembly, this building block enables rapid generation of analog series where N-methylation is used as a design element to tune local structure, reduce undesired aggregation, and improve synthetic tractability during library synthesis. Researchers commonly incorporate this residue into lead-optimization efforts for receptor-binding peptides and cell-surface interaction probes, where defined side-chain protection and controlled coupling behavior are critical for reproducible library manufacture.
3. Segment Condensation Intermediates
Boc-N-Me-Arg(Mtr)-OH is also employed in solution-phase segment condensation and custom peptide intermediate preparation, where protected amino acid residues must be carried through multiple coupling and purification steps without guanidinium side-chain interference. The Mtr group helps maintain the arginine side-chain in a protected, non-reactive state during activation and coupling of peptide fragments, supporting the assembly of longer constructs and difficult sequences. In practice, peptide manufacturing groups and contract synthesis teams use this building block to prepare Arg-containing segments with consistent functional-group protection, improving the reliability of downstream fragment coupling and minimizing byproduct formation associated with unprotected guanidinium chemistry.
4. Protected Amino Acid Building Block
Boc-N-Me-Arg(Mtr)-OH serves as a specialized protected amino acid building block for researchers who need N-methylated arginine functionality with robust side-chain protection. This format is frequently selected when standard arginine building blocks lead to lower synthetic yield or complicate purification due to side reactions, charge-related aggregation, or incomplete selectivity during peptide assembly. By combining N-terminal Boc protection with Mtr-protected guanidinium, the reagent provides a practical input for constructing well-defined peptide intermediates and final products in workflows that prioritize reproducibility, functional-group stability, and controlled incorporation of modified arginine residues.
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