Boc-L-Arg(Mts)-OH*CHA is a protected derivative of the amino acid arginine, featuring a Boc-protected α-amino group and an arginine side chain bearing an Mts (thioether/thiol-protecting) group, along with a free carboxylic acid functionality. The molecule is specified as the L-arginine stereochemical form, and its guanidinium-containing side chain is structurally masked by the Mts substituent to control chemoselectivity during peptide bond formation while retaining the underlying arginine functionality for later deprotection. It is used as a stepwise building block in protected amino acid chemistry and peptide synthesis workflows where the Boc group and Mts-protected side chain support selective coupling and minimize undesired side reactions of the strongly basic guanidinium moiety.
CAT No: CP25987
CAS No:68262-71-5
Synonyms/Alias:Boc-Arg(Mts)-OH;136625-03-1;68262-71-5;Boc-Arg(Mts)-OH.CHA;Boc-arginine(mts)-OHcha;15545_ALDRICH;B7144_SIGMA;15545_FLUKA;C20H32N4O6S;MolPort-003-926-849;6271AH;CB-930;ZINC15721284;Boc-Arg(Mts)-OHcyclohexylaminesalt;AKOS015902544;AC-19253;AK170132;FT-0641173;FT-0687201;ST51055554;I14-7021;I14-19487;I14-43296;alpha-Boc-Arg(Nomega-Mesitylenesulfonyl)-OHcyclohexylammoniumsalt;Nalpha-Boc-Nomega-(mesitylene-2-sulfonyl)-L-argininecyclohexylaminesalt
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-(mesitylene-2-sulfonyl)-L-arginine cyclohexylamine
Boc-L-Arg(Mts)-OH*CHA is an Fmoc-free, Boc-protected L-arginine building block bearing an Mts-protected side chain and supplied as a salt/complex with *CHA (counterion/solvate form). The combination of Boc on the alpha-amino group and Mts on the guanidinium side chain is designed to support controlled peptide assembly while minimizing undesired side reactions during coupling and deprotection steps. This protected arginine derivative is widely used in peptide synthesis workflows where reliable handling of the strongly basic guanidinium functionality is required.
1. Solid-Phase Peptide Synthesis
Boc-L-Arg(Mts)-OH*CHA is used by peptide synthesis groups to incorporate an arginine residue into protected peptide sequences with predictable reactivity under standard Boc-compatible coupling and deprotection conditions. The Mts protection on the guanidinium side chain helps suppress side reactions associated with the highly nucleophilic/basic arginine functionality, which is particularly valuable when building longer sequences or assembling arginine-rich motifs. Peptide manufacturers and academic peptide chemistry labs commonly select this type of arginine building block to improve coupling consistency and to support downstream purification of crude peptide intermediates.
2. Boc-Based Segment Coupling
Boc-L-Arg(Mts)-OH*CHA is also applied in solution-phase or segment condensation strategies where Boc-protected amino acid derivatives are assembled into larger peptide fragments prior to final coupling. In these workflows, the orthogonal protection pattern provided by Boc at the N-terminus and Mts on the side chain is leveraged to manage compatibility across multiple synthesis steps and to reduce guanidinium-related complications during fragment assembly. Pharmaceutical intermediate development teams and custom peptide synthesis providers often use this protected arginine building block to prepare defined peptide intermediates for subsequent manufacturing or research-grade peptide production.
3. Arginine-Rich Peptide Building
Boc-L-Arg(Mts)-OH*CHA is frequently chosen for constructing peptides where arginine content and basicity can complicate synthesis, such as cell-penetrating peptide sequences, receptor-binding peptides, and other arginine-rich constructs used in chemical biology. The protected guanidinium functionality enables incorporation of arginine residues without premature side-chain reactivity, supporting iterative assembly and better control over crude material complexity. Researchers developing peptide probes, peptide ligands, and peptide-based materials typically value this building block for its practical handling in peptide workflows that require stable protection of the arginine side chain through key steps of synthesis and purification.
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