N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is a protected, D-configured arginine derivative in which the α-amino group is masked with an Fmoc group and the ω and ω′ guanidinium nitrogens are protected as allyloxycarbonyl (Alloc) carbamates. The molecule bears a free carboxyl functional group while the side-chain guanidinium functionality is rendered as two N-Alloc-protected carbamates, controlling chemoselectivity during stepwise peptide assembly and limiting undesired side reactions of the strongly basic guanidinium. In peptide chemistry, this protected amino acid is employed as a building block for solid-phase or solution-phase synthesis where orthogonal Fmoc/Alloc deprotection enables sequential exposure of the amino and guanidinium functionalities for subsequent coupling and incorporation into peptide targets.
CAT No: CP00216
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is a D-configuration arginine derivative designed for orthogonally protected peptide chemistry, combining an Fmoc group on the α-amino position with two allyloxycarbonyl (Alloc) protecting groups on the ω and ω′ nitrogens of the guanidinium side chain. The molecule therefore presents a protected α-amino functionality for stepwise solid-phase peptide coupling while masking the strongly basic guanidinium to control chemoselectivity during chain assembly. The D stereocenter at the α-position supports stereochemically defined incorporation of D-arginine into peptides and peptide-like scaffolds, enabling studies that distinguish D- versus L-arginine effects on folding, proteolysis resistance, and receptor recognition. Alloc groups can be removed under orthogonal conditions relative to Fmoc, and the guanidinium functional motif can be regenerated for subsequent derivatization, conjugation, or binding-site mimicry.
1. Peptide Synthesis
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is applied in automated and manual peptide synthesis where Fmoc protection enables reliable α-amino coupling cycles while the di-Alloc guanidinium protection suppresses side reactions from the strongly basic side chain. The protected guanidinium nitrogens remain masked during peptide bond formation, supporting cleaner coupling and minimizing undesired salt formation or aggregation that can complicate peptide assembly. Orthogonal deprotection of the Alloc groups can regenerate the free guanidinium for late-stage functionalization or for producing arginine-containing segments with controlled exposure timing. D-arginine stereochemistry further enables peptide synthesis strategies for protease-resistant analogs and stereochemically defined structure-function studies, extending the compound's role as a protected amino acid building block in peptide science and synthetic methodology development.
2. Chemical Biology
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is used in chemical biology workflows that require guanidinium-bearing motifs for molecular recognition, membrane interactions, or protein-binding mimicry. The orthogonally protected design allows researchers to incorporate a D-arginine residue into peptides or peptidomimetics while deferring guanidinium unmasking until after the desired scaffold is assembled. The regenerated guanidinium can participate in electrostatic and hydrogen-bonding interactions, supporting downstream conjugation steps such as installing linkers, affinity handles, or charge-modulating groups on peptide derivatives. D stereochemistry can be leveraged to probe how stereochemical inversion influences binding selectivity, stability, and cellular processing of arginine-rich constructs, making this derivative relevant to amino acid derivatization and protected amino acid synthesis for biochemical research intermediate preparation.
3. Bioconjugation Chemistry
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is suitable for bioconjugation strategies that rely on orthogonal protection to control when the guanidinium side chain becomes reactive for subsequent coupling or labeling. The Fmoc group supports peptide assembly or linker installation under standard amino-protection logic, while the di-Alloc groups enable selective deprotection to reveal the guanidinium functionality without disturbing other protecting groups. The free guanidinium can then serve as a functional handle for constructing conjugates that exploit cationic charge density, including attachment of targeting moieties or formation of peptide-based delivery vectors. Incorporation of D-arginine can also be used to tune conjugate stability against enzymatic degradation, supporting the generation of defined bioconjugation intermediates for analytical research and applied molecular design.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is employed in peptidomimetic construction and structure-activity relationship studies where stereochemically defined arginine analogs help map how side-chain charge presentation affects binding and activity trends. The protected α-amino group and masked guanidinium enable incorporation into peptide analogs, cyclic peptides, or constrained scaffolds using peptide coupling chemistry without premature side-chain reactivity. Alloc deprotection can be used to regenerate the guanidinium for later-stage modifications such as introducing additional functional substituents or preparing analog series with controlled cationic character. D-arginine incorporation supports SAR designs that differentiate stereochemical contributions to receptor or protein interactions, aligning the compound with medicinal chemistry-oriented amino acid derivatization and protected amino acid chemistry for research-grade library synthesis.
5. Pharmaceutical Manufacturing Intermediates
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is relevant to pharmaceutical manufacturing and process chemistry as a protected amino acid intermediate used to prepare arginine-containing peptide intermediates under orthogonal protection schemes. The Fmoc/Alloc architecture supports stepwise assembly logic and controlled deprotection sequencing, which can be integrated into scalable solid-phase or solution-phase peptide manufacturing routes for producing D-arginine-containing drug candidates or reference standards. The guanidinium masking by di-Alloc groups helps manage chemoselectivity and reduces side reactions during upstream coupling operations, while the ability to regenerate the free guanidinium supports downstream formation of final peptide intermediates and conjugation-ready derivatives. D stereochemistry provides a defined chiral input for manufacturing of stereochemically consistent peptide materials, supporting consistent downstream analytical characterization and enabling fine chemical synthesis of protected amino acid derivatives for industrial peptide science.
6. Analytical Research Standards
N-α-Fmoc-N-ω-,N-ω′-di-allyloxycarbonyl-D-arginine is used in analytical research contexts to generate defined peptide fragments and reference materials that contain a D-arginine residue with a protected-to-unmasked guanidinium conversion pathway. The presence of Fmoc and Alloc protecting groups supports controlled synthesis of labeled or modified peptide standards, where orthogonal deprotection allows preparation of guanidinium-exposed forms for mass spectrometric identification and chromatographic method development. The stereodefined D configuration supports analytical discrimination of stereoisomeric peptide components, aiding studies that require separation or verification of D- versus L-arginine-containing sequences. The compound's compatibility with peptide building block preparation therefore supports downstream derivative formation for method validation, impurity profiling, and structural confirmation in biochemical research and industrial quality-focused analytical workflows.
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