N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine is a protected, derivative form of the amino acid arginine in which the α-amino group is masked with an Fmoc protecting group and both guanidinium nitrogens are protected as allyloxycarbonyl (Alloc) carbamates. The molecule retains the L-configuration at the α-carbon and features a side-chain guanidinium functionality that is rendered non-basic by double Alloc protection, while the carboxyl group remains available for peptide coupling after deprotection of the relevant groups. In peptide synthesis workflows, this orthogonally protected arginine analogue is employed to control chemoselectivity during stepwise assembly and to enable later deprotection of the Alloc groups to regenerate the guanidinium side chain for incorporation into peptide targets or for subsequent derivatization.
CAT No: CP00217
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine is an Fmoc-protected L-arginine derivative designed for orthogonally protected guanidinium chemistry. The molecule contains an α-amino group masked with the Fmoc carbamate for base-labile deprotection during solid-phase peptide synthesis, while the ω and ω′ nitrogens of the arginine side-chain guanidinium are protected as allyloxycarbonyl (Alloc) carbamates. The stereogenic center at the L-α-position is preserved, supporting stereochemically defined peptide bond formation and downstream fragment assembly. As an amino acid building block bearing protected nucleophilic functionality, it participates in standard peptide coupling while enabling selective deprotection strategies that preserve the guanidinium functionality for later conjugation, binding-site mimicry, or enzymatic recognition studies.
1. Peptide Synthesis
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine is used as a protected arginine building block for Fmoc-based peptide synthesis where orthogonal deprotection is required. The Fmoc group on the α-amino terminus supports controlled N-terminal activation and coupling cycles, while the Alloc-protected guanidinium nitrogens remain masked to prevent side reactions during chain elongation. Selective removal of Alloc under conditions compatible with peptide-resin and other protecting groups can regenerate the guanidinium functionality for subsequent coupling or for final peptide deprotection workflows. The resulting arginine-containing peptides and peptide fragments are suitable for generating defined cationic sequences used in peptide science, chemical biology probes, and peptidomimetic scaffolds that require a protected, stereochemically consistent arginine side chain.
2. Side-Chain Functionalization
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine supports side-chain functionalization strategies that depend on temporally protected guanidinium reactivity. The Alloc carbamates on both ω and ω′ nitrogens provide a controlled handle for selective unmasking to yield a free, strongly basic guanidinium group after peptide or intermediate assembly. The preserved L-configuration and protected guanidinium enable downstream transformations such as guanidinium-directed conjugation, salt-formation tuning, and incorporation into binding-site mimics where cationic charge distribution is critical. The compound can therefore serve as a synthetic intermediate for constructing cationic peptide analogs and functionalized amino acid derivatives used in molecular recognition studies and materials-oriented cationic surface chemistry.
3. Bioconjugation Chemistry
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine is applicable to bioconjugation workflows that require orthogonal protection of the arginine guanidinium during synthesis of conjugatable biomolecules. The Fmoc-protected α-amino group and the dual Alloc protection on the guanidinium nitrogens allow sequential assembly of peptide linkers or targeting motifs while minimizing undesired guanidinium interactions with electrophiles or activated coupling reagents. Selective deprotection can generate a free guanidinium for subsequent conjugation steps, including incorporation into peptide-based linkers for labeling, affinity capture reagents, or cell-surface binding constructs. The resulting conjugation-ready intermediates align with amino acid chemistry practices that separate backbone assembly from side-chain unveiling, supporting reproducible functional group presentation for biochemical research and applied labeling reagent production.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine is used in peptidomimetic construction and structure-activity relationship studies where arginine side-chain presentation must be stereochemically and charge-controlled. The protected guanidinium enables incorporation into analog libraries without premature guanidinium reactivity, while the Fmoc strategy supports systematic variation of neighboring residues and linker architectures. Alloc deprotection can be timed to match downstream modifications such as cyclization, stapling, or conjugate attachment that require a defined cationic center for binding interactions. The compound thus serves as a chiral, protected amino acid intermediate for generating arginine-containing analogs used in SAR mapping, fragment refinement, and molecular design efforts that rely on consistent charge and geometry across series.
5. Pharmaceutical Manufacturing Intermediates
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-L-arginine is relevant to pharmaceutical manufacturing and fine chemical production as a protected amino acid intermediate for producing cationic peptide intermediates under controlled synthetic protection schemes. The orthogonal Fmoc/Alloc protection pattern supports manufacturing-friendly workflows in which backbone assembly and side-chain deprotection are decoupled, improving handling of the guanidinium functionality during multi-step synthesis. The compound's defined L-stereochemistry supports stereochemically consistent peptide fragments used in process chemistry for generating drug-like peptide candidates, peptide-based intermediates, or peptide-derived building blocks for further derivatization. The resulting downstream materials can be integrated into scalable peptide synthesis routes where selective deprotection and functional group timing are central to reproducible intermediate generation and downstream purification strategy.
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