N-α-Fmoc-N-γ-xanthyl-D-asparagine is a protected, derivatized amino acid in which the α-amino group is masked with an Fmoc group and the side-chain amide of D-asparagine is further substituted to form an N-γ-xanthyl (xanthyl) functionality. The molecule contains a carboxyl group and an Fmoc-protected α-amino group, while the side-chain bears an additional amide-type substituent that modulates hydrogen-bonding and reactivity compared with unmodified asparagine, with D stereochemistry indicated by the product name. It is used as a building block for stepwise peptide synthesis and related chemical biology workflows where controlled chemoselectivity of the α-amino functionality and a protected/functionalized asparagine side chain are required for assembling peptide analogues or for preparing structurally defined peptide intermediates.
CAT No: CP00318
N-α-Fmoc-N-γ-xanthyl-D-asparagine is an Fmoc-protected D-asparagine derivative in which the side-chain amide is masked with a xanthyl (xanthate-like) protecting group at the γ-nitrogen. The molecule contains a chiral α-center characteristic of D-asparagine, an Fmoc carbamate on the α-amino functionality for base-labile peptide assembly, and a protected side-chain nitrogen that modulates hydrogen-bonding and nucleophilicity during coupling and subsequent transformations. The xanthyl group provides a distinct protection strategy for the side-chain amide, enabling controlled unveiling or functional conversion under conditions selected for xanthyl chemistry while suppressing undesired side reactions. The resulting protected amino acid building block is designed for compatibility with iterative solid-phase or solution-phase peptide construction and for downstream synthesis of asparagine-derived motifs and side-chain functionalized analogs.
1. Peptide Synthesis
N-α-Fmoc-N-γ-xanthyl-D-asparagine is applied in peptide building block preparation for automated solid-phase peptide synthesis and protected amino acid chemistry workflows. The Fmoc group on the α-amino terminus supports standard Fmoc deprotection logic, enabling sequential N-terminal peptide bond formation while maintaining the side-chain functionality in a masked state. The D-asparagine stereochemistry provides a defined chiral center that can be incorporated into peptide sequences to control conformational preferences and stereochemical outcomes in asparagine-containing segments. The xanthyl-protected γ-amide nitrogen can be carried through coupling steps to reduce side-chain reactivity, supporting later side-chain deprotection or conversion to asparagine-derived derivatives for peptide analog construction.
2. Side-Chain Functionalization
N-α-Fmoc-N-γ-xanthyl-D-asparagine is suitable for side-chain functionalization strategies where controlled manipulation of the asparagine γ-amide is required after peptide assembly or during intermediate synthesis. The xanthyl protection at the γ-nitrogen changes the effective polarity and nucleophilicity of the side chain, allowing chemoselective transformations that target the amide-derived functionality without perturbing the peptide backbone. The protected amino acid derivative can be used to access aspartamide/asparagine-related motifs, including side-chain modifications that require temporary masking of the amide nitrogen to manage reactivity during multi-step syntheses. Downstream conversion of the side-chain protected group can enable generation of functionalized peptide fragments and peptidomimetic scaffolds bearing asparagine-derived substitution patterns.
3. Chemical Biology Probes
N-α-Fmoc-N-γ-xanthyl-D-asparagine supports chemical biology research where labeled or reactive asparagine analogs are needed for studying biomolecular recognition and post-synthetic modification. The Fmoc-protected α-amino group facilitates incorporation into peptide or peptidomimetic constructs, while the protected γ-amide nitrogen enables staged functionalization to introduce handles for conjugation chemistry. The defined D-configuration can be leveraged to tune stability against proteolysis and to influence local structure in probe peptides used for binding studies or targeted labeling strategies. Side-chain unmasking or conversion from the xanthyl-protected state can provide access to reactive intermediates for downstream derivatization, enabling construction of biomolecule-modifying reagents and research-grade peptide probes.
4. Peptidomimetics And SAR
N-α-Fmoc-N-γ-xanthyl-D-asparagine is employed in peptidomimetic construction and structure-activity relationship studies requiring controlled stereochemistry and side-chain chemistry. The compound's chiral D-asparagine backbone and protected amide functionality allow systematic variation of asparagine-derived features while keeping coupling-compatible protection during scaffold assembly. The Fmoc group supports iterative synthesis of analog series, whereas the xanthyl-protected γ-nitrogen can be used to regulate side-chain reactivity so that SAR-driven modifications can be introduced at a controlled stage. The resulting asparagine-containing analogs can serve as defined chemical entities for mapping how side-chain electronics, hydrogen-bonding capacity, and stereochemical placement affect molecular recognition in medicinal chemistry and biochemical assay development.
5. Process Chemistry Intermediate
N-α-Fmoc-N-γ-xanthyl-D-asparagine is relevant to process chemistry intermediate preparation for fine chemical synthesis routes that require robust protection-group management across multi-step manufacturing. The Fmoc carbamate provides operationally manageable protection for the α-amino group during peptide coupling chemistry, while the γ-xanthyl protection offers an alternative side-chain masking strategy that can be selected to match downstream deprotection or conversion steps. The presence of a single stereogenic center simplifies stereochemical tracking and can support reproducible incorporation into peptide building blocks for downstream intermediate generation. The compound can be used as a controlled chiral precursor for producing protected asparagine derivatives and asparagine-containing peptide intermediates at scale, aligning with industrial workflows that prioritize protection compatibility, chemoselectivity, and reproducible intermediate handling.
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