Boc-Arg(Pmc)-OH is a protected arginine amino acid derivative bearing an N-terminal Boc (tert-butoxycarbonyl) protecting group and a side-chain guanidinium protected as the Pmc (2,2,5,7,8-pentamethylchroman-6-sulfonyl) carbamate-type protecting group. The molecule contains both an amino functionality and a carboxylic acid, with the arginine side chain providing a guanidinium motif that is masked by Pmc to control chemoselectivity during peptide coupling and to reduce undesired side reactions. In peptide synthesis workflows, the orthogonally protected arginine form supports stepwise assembly of peptides by keeping the reactive guanidinium group protected while the carboxyl and N-protected amine participate in controlled bond formation.
CAT No: CP26624
CAS No:200125-12-8
Synonyms/Alias:BOC-ARG(PMC)-OH;200125-12-8;Nalpha-Boc-Nomega-(2,2,4,6,7-pentamethylchroman-6-sufonyl)-L-arginine;C25H40N4O7S;CTK8F0156;6272AH;ZINC71788030;RT-014652;K-5845
Boc-Arg(Pmc)-OH is a protected arginine building block designed for peptide synthesis, featuring an N-terminal Boc protecting group and a side-chain-protected guanidinium functionality using Pmc. This orthogonally protected arginine derivative supports controlled assembly of peptides where the guanidinium must be masked during coupling and revealed at a later stage for native-like charge presentation in the final product. Researchers and custom peptide manufacturers rely on this specific protection pattern to improve handling and minimize side reactions associated with unprotected arginine during multistep synthesis.
1. Solid-Phase Peptide Synthesis
Boc-Arg(Pmc)-OH is widely used in solid-phase peptide synthesis workflows to incorporate arginine residues in sequences where side-chain guanidinium protection is required for reliable coupling and purification. Peptide synthesis groups and peptide CROs select this protected amino acid to maintain the guanidine functionality in a masked state during chain elongation, supporting the preparation of longer, more complex peptides that contain multiple basic residues. The Boc group enables standard N-terminal deprotection cycles in protected amino acid strategies, while the Pmc side-chain protection is chosen to better manage chemoselectivity during assembly and downstream processing of the peptide.
2. Modified Peptide Building Blocks
Boc-Arg(Pmc)-OH is commonly used when preparing peptides that require precise placement of arginine and controlled exposure of the side-chain during post-synthetic steps. Chemical biology laboratories developing arginine-containing peptide probes, receptor-binding peptides, or cell-penetrating peptide variants often prefer this derivative because it provides a protected arginine handle that can be carried through synthesis without premature side-chain reactivity. In these programs, the Pmc-protected guanidinium is particularly valuable for maintaining sequence integrity during iterative coupling and for enabling downstream conversion to the desired charged arginine side chain in the final peptide material.
3. Pharmaceutical Intermediate Peptide Segments
Boc-Arg(Pmc)-OH is also used in pharmaceutical intermediate development to generate arginine-containing peptide segments for medicinal chemistry and peptidomimetic programs. Process development teams and custom synthesis providers apply this building block to assemble protected peptide intermediates that can be carried into subsequent conjugation, fragment coupling, or final deprotection steps under controlled conditions. The Boc/Pmc protection pattern helps support reproducible manufacturing workflows for basic-residue-containing sequences, where managing guanidinium reactivity and maintaining peptide purity are critical for downstream intermediate handling.
4. Peptide Library Construction
Boc-Arg(Pmc)-OH serves as a practical arginine component for peptide library construction and structure-activity relationship (SAR) studies that require systematic variation of neighboring residues while keeping the arginine side chain protected during synthesis. Research groups building small to medium peptide libraries use this derivative to standardize arginine incorporation across many analogs, improving comparability of library members after purification and final deprotection. The protected guanidinium functionality helps reduce sequence-dependent synthesis variability that can arise when basic side chains are not adequately masked during multistep peptide assembly.
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