Boc-Arg-SBzl · HCl is a Boc-protected arginine derivative bearing an SBzl (S-benzyl) side-chain protection on the guanidinium functionality, with the amino acid backbone containing a free carboxyl group and an N-terminal carbamate. The molecule contains the Boc carbamate as a chemoselective protecting group for the α-amino group, while the side-chain guanidinium is masked as a benzyl-protected form and the compound is present as a hydrochloride salt, which affects the protonation state of the basic functionalities during handling and coupling. In peptide synthesis and amino acid derivative assembly, this protected arginine analogue is used as a stepwise building block to control side-chain reactivity and support selective formation of peptide bonds under conditions compatible with Boc deprotection and guanidinium side-chain masking.
CAT No: CP27491
CAS No:79864-22-5
Synonyms/Alias:Boc-Arg-SBzl.HCl;AM001700;79864-22-5;TERT-BUTYLN-[(2S)-1-(BENZYLSULFANYL)-5-CARBAMIMIDAMIDO-1-OXOPENTAN-2-YL]CARBAMATEHYDROCHLORIDE
Boc-Arg-SBzl · HCl is a protected arginine derivative designed for peptide synthesis workflows, featuring an N-terminal Boc protecting group and a side-chain SBzl (S-benzyl) protection strategy that helps control guanidinium reactivity during coupling and deprotection steps. Supplied as the hydrochloride salt, it is commonly handled in peptide chemistry as a stable, cationic building block for constructing arginine-containing sequences with minimized side reactions. This protected amino acid form is selected by peptide chemists when robust guanidinium protection is required to support efficient segment assembly and downstream deprotection.
1. Solid-Phase Peptide Synthesis
Boc-Arg-SBzl · HCl is used by peptide synthesis groups to introduce arginine residues into peptide chains under solid-phase peptide synthesis conditions, where orthogonal control of the guanidinium functionality is essential for clean coupling and sequence fidelity. The Boc group supports standard N-terminal activation/deprotection cycles, while the SBzl-protected side chain helps prevent premature guanidinium participation or undesired side reactions during chain elongation. Peptide manufacturers and academic peptide cores frequently select this building block for routine synthesis of arginine-rich peptides, including longer sequences where side-chain stability during repeated deprotection and coupling steps is a practical concern.
2. Protected Segment Building Blocks
Boc-Arg-SBzl · HCl serves as a reliable arginine unit for preparing protected peptide segments used in solution-phase peptide synthesis and convergent assembly strategies. In these workflows, side-chain protection of the arginine guanidinium is a key requirement to maintain segment integrity while enabling selective activation at the intended coupling site. Contract peptide synthesis providers and process-development chemists often rely on this type of protected arginine derivative when building blocks must tolerate multiple coupling operations and subsequent global deprotection, supporting the preparation of intermediate fragments that can be condensed into larger targets.
3. Arginine-Rich Peptide Development
Boc-Arg-SBzl · HCl is frequently selected for developing peptides where arginine content is high and guanidinium handling becomes a dominant practical variable, such as in peptide libraries, binding peptides, and cell-penetrating peptide research materials. The protected guanidinium functionality allows chemists to manage solubility and reactivity during synthesis without exposing the free side chain until the final deprotection stage. Researchers preparing arginine-containing analogs for structure-activity relationship studies or for downstream conjugation steps often prefer this protected arginine form to reduce variability caused by side-chain reactivity during iterative synthesis and purification.
4. Pharmaceutical Intermediate Peptide Synthesis
Boc-Arg-SBzl · HCl is also used in the preparation of protected peptide intermediates that feed into pharmaceutical intermediate development programs, particularly when arginine-containing motifs must be assembled under controlled protecting-group strategies. Process chemists and medicinal chemistry groups use this building block to construct defined peptide fragments with consistent side-chain protection, supporting subsequent transformations that depend on predictable deprotection behavior. This makes the derivative a practical choice for manufacturing-focused peptide intermediate routes where reproducibility of protected arginine incorporation is important for downstream scale-up and analytical traceability.
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