N-α-Fmoc-N-ω-tosyl-D-arginine is a protected D-arginine derivative in which the α-amino group is Fmoc-protected and the ω-amino group is tosyl-protected, retaining the arginine guanidinium side-chain framework while converting both amino functionalities into masked forms. The molecule contains a free carboxyl group and an arginine side chain bearing a guanidinium moiety whose terminal amino is sulfonamide-protected by a tosyl group, with the stereochemistry explicitly specified as D at the α-carbon. This compound is used as a peptide-synthesis building block to control chemoselectivity during stepwise assembly, support orthogonal protection of the α- and side-chain amino groups, and enable incorporation of the protected arginine residue into protected peptide intermediates for subsequent deprotection and downstream labeling or structure-activity studies.
CAT No: CP00224
N-α-Fmoc-N-ω-tosyl-D-arginine is a protected D-configured arginine derivative featuring an Fmoc group on the α-amino functionality and a tosyl (p-toluenesulfonyl) group on the ω-guanidino nitrogen set, yielding a doubly protected amino acid building block suitable for controlled peptide assembly. The molecule retains the arginine side-chain carbon skeleton while masking the strongly basic guanidinium chemistry, and the Fmoc carbamate provides an acid-labile handle for stepwise deprotection during solid-phase or solution-phase synthesis. The stereogenic center at the α-carbon is fixed in the D-configuration, enabling stereochemically defined incorporation into peptide analogs and chiral SAR libraries. The combination of aromatic sulfonyl protection and Fmoc carbamate protection modulates hydrogen-bonding and nucleophilicity, supporting stable handling as a chiral intermediate for peptide coupling and downstream functional transformations.
1. Peptide Synthesis
N-α-Fmoc-N-ω-tosyl-D-arginine is used in peptide synthesis as a protected arginine residue compatible with standard peptide coupling chemistries, where the Fmoc group enables orthogonal N-terminal protection and the ω-tosyl protection suppresses guanidino reactivity during chain elongation. The protected guanidino motif preserves the arginine side-chain topology while preventing premature side reactions such as undesired salt formation or nucleophilic interference in coupling steps. Controlled Fmoc deprotection reveals the α-amino functionality for sequential bond formation, while the tosyl-protected side chain can be retained through multiple cycles to maintain chemoselectivity. Resulting peptides and peptide fragments can then be carried forward to guanidinium-unmasked forms for further biochemical evaluation, conjugation, or structural studies that require arginine-like charge distribution.
2. Peptidomimetics And SAR
N-α-Fmoc-N-ω-tosyl-D-arginine supports peptidomimetic and SAR studies by enabling incorporation of a D-arginine stereocenter into peptide-like scaffolds that probe stereochemical effects on folding, receptor binding, and protease resistance. The Fmoc-protected α-amino group facilitates assembly of defined sequences, while ω-tosyl protection maintains a masked guanidino functionality that can be selectively unmasked after scaffold construction. The resulting D-arginine-containing analogs can be used to generate structure-activity relationship panels by varying sequence context and side-chain presentation without changing the protected building block handling. Downstream deprotection and side-chain activation steps can yield analogs with controlled cationic character, supporting systematic comparison of stereochemical and charge-dependent molecular recognition.
3. Chemical Biology Conjugation
N-α-Fmoc-N-ω-tosyl-D-arginine is applied in chemical biology workflows where arginine-containing peptides are prepared for labeling, affinity capture, and biomolecule modification strategies that rely on guanidinium-mediated interactions. The protected guanidino group reduces uncontrolled binding and aggregation during synthesis and purification, while the Fmoc handle enables stepwise generation of reactive peptide termini for conjugation-ready intermediates. Deprotection of the α-amino functionality supports generation of peptide fragments that can be further functionalized at termini or side chains using standard derivatization approaches. The D-configuration can be leveraged to tune binding selectivity and stability of conjugates used as research reagents, enabling reproducible preparation of charged peptide conjugates for downstream assays and biomolecular interaction studies.
4. Protected Amino Acid Chemistry
N-α-Fmoc-N-ω-tosyl-D-arginine serves as a protected amino acid chemistry intermediate for developing orthogonally protected arginine derivatives and for tuning protection strategies across multi-functional peptide building blocks. The Fmoc carbamate and ω-tosyl sulfonamide protection pattern provides chemoselective control over deprotection order, supporting workflows where α-amino exposure and side-chain masking must be maintained independently. The D-stereochemistry is preserved through the protection and coupling stages, allowing stereodefined intermediate preparation for chiral synthesis campaigns and stereochemical library generation. The compound can be employed to prepare downstream guanidinium-unmasked arginine residues or to generate further protected derivatives that maintain compatibility with peptide coupling and iterative synthetic assembly.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-ω-tosyl-D-arginine is suitable for pharmaceutical intermediate preparation where protected arginine residues are required for manufacturing of peptide-based research materials, process development batches, and defined peptide intermediates. The dual protection strategy supports robust handling under typical peptide synthesis conditions by limiting side-chain reactivity and enabling predictable coupling behavior of the α-amino group after Fmoc removal. The resulting protected peptide fragments can be advanced toward final deprotected forms used as defined starting materials for formulation-relevant studies, analytical method development, or further synthetic elaboration. Industrial process chemistry benefits from the compound's stable, isolable protected form that integrates stereochemical control and orthogonal deprotection logic into peptide manufacturing routes.
6. Analytical Research Standards
N-α-Fmoc-N-ω-tosyl-D-arginine is utilized in analytical research as a chiral, protected reference material for method development and characterization of arginine-containing peptide products. The defined D-configuration and the presence of Fmoc and tosyl protecting groups provide characteristic mass and chromatographic signatures that can be used to confirm identity, monitor deprotection progression, and validate peptide synthesis workflows. The masked guanidino functionality helps maintain consistent behavior during sample preparation, supporting reproducible analysis of intermediates and partially deprotected species. Incorporation into defined peptide standards can further enable targeted LC-MS or MS/MS method validation for stereochemically defined arginine residues and for monitoring side-chain protection state during synthetic and analytical campaigns.
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