N-α-Fmoc-D-asparagine is a protected amino acid derivative of asparagine in which the α-amino group is carbamated with an Fmoc (9H-fluoren-9-ylmethoxycarbonyl) protecting group and the side chain contains a primary amide. The molecule bears a free carboxyl group and a D stereochemical configuration at the α-carbon as indicated by the name, with the side-chain amide functioning as a hydrogen-bonding polar group that can participate in peptide secondary-structure interactions. N-α-Fmoc-D-asparagine is used as a building block in peptide synthesis and related chemical biology workflows, where the Fmoc protection supports stepwise assembly while the asparagine side-chain amide provides a defined functional motif for structure-activity and labeling studies.
CAT No: CP00314
CAS No:108321-39-7
Synonyms/Alias:Fmoc-D-Asn-OH;Fmoc-D-asparagine;108321-39-7;Nalpha-Fmoc-D-asparagine;Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-asparagine;AmbotzFAA1468;PubChem10003;FMOC-D-ASN;N-|A-Fmoc-D-asparagine;47441_ALDRICH;N-A-FMOC-D-ASPARAGINE;SCHEMBL119451;47441_FLUKA;CTK0H4378;MolPort-006-666-304;ACT04983;ZINC1576230;ANW-15927;CF-132;AB02463;AM81559;RTR-001937;AC-17098;AJ-27298;AK-49241
N-α-Fmoc-D-asparagine is an Fmoc-protected D-asparagine derivative in which the α-amino group is masked by the 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) protecting group, while the side-chain amide of asparagine remains unprotected and available for hydrogen-bonding and further functionalization. The D-configuration at the α-stereocenter provides stereochemical control for incorporation into peptide sequences where non-natural chirality is required for stability, selectivity, or conformational tuning. The molecule contains an Fmoc aromatic system that supports standard base-labile deprotection under peptide synthesis conditions, and it also presents a carboxamide functionality that can participate in coupling-adjacent interactions and downstream derivatization. As a chiral, protected amino acid building block, N-α-Fmoc-D-asparagine functions as a practical intermediate for constructing protected peptide fragments and for preparing stereodefined asparagine-containing analogs used in biochemical and synthetic organic workflows.
1. Peptide Synthesis
N-α-Fmoc-D-asparagine is used in solid-phase peptide synthesis workflows to introduce a D-asparagine residue with an Fmoc-protected α-amine compatible with stepwise peptide coupling cycles. The Fmoc group enables base-mediated deprotection to reveal the reactive amine for amide bond formation, while the side-chain carboxamide remains present to support amide-to-amide hydrogen bonding patterns in the growing sequence. D-stereochemistry at the α-center allows access to stereochemically defined peptide backbones and asparagine-containing analogs that can be used to probe backbone recognition and conformational effects. Downstream, the residue can be incorporated into protected peptide fragments that serve as intermediates for full-length peptide assembly, fragment ligation, and derivatized peptide library construction in peptide chemistry programs.
2. Chemical Biology
N-α-Fmoc-D-asparagine is applied in chemical biology research where D-amino acid incorporation is used to modulate peptide stability and molecular recognition in protein-binding or nucleic-acid-associated assays. The persistent side-chain amide provides a polar handle for studying hydrogen-bond networks and for designing peptidic probes that retain asparagine-like interaction geometry while altering stereochemical preferences. Fmoc protection supports controlled synthesis of labeled or modified peptide constructs, enabling systematic variation of stereochemistry at the asparagine position without changing the core functional group pattern. Resulting D-asparagine-containing peptides and peptidomimetics can be employed as biochemical research intermediates for molecular recognition studies, interaction mapping, and structure-activity relationship experiments that depend on precise stereodefined building blocks.
3. Side-Chain Functionalization
N-α-Fmoc-D-asparagine is suitable for side-chain functionalization strategies that transform the asparagine carboxamide into alternative amide, urea, or substituted functionalities while retaining the peptide-compatible α-amino protection logic. The side-chain amide can undergo chemoselective activation and subsequent derivatization to generate analogs with altered polarity, sterics, or binding motifs, which is useful for creating asparagine replacements in peptidomimetics and SAR-focused libraries. The Fmoc group allows orthogonal handling during multi-step synthesis, supporting sequential protection, deprotection, and coupling steps in a manner consistent with protected amino acid chemistry. Downstream products include functionalized D-asparagine-derived peptide building blocks and stereodefined intermediates for generating modified peptide scaffolds used in applied synthetic organic chemistry and target-guided molecular design.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-D-asparagine is used in peptidomimetic construction and structure-activity relationship studies where maintaining an asparagine-like side-chain while changing backbone stereochemistry can tune conformation and receptor contact patterns. The chiral D-configuration provides a stereochemical variable that can be systematically introduced into peptide analogs to evaluate the contribution of stereochemistry to binding or activity profiles in screening workflows. The Fmoc-protected α-amine supports consistent incorporation into peptide-like scaffolds, enabling generation of analog series that differ at specific positions while keeping coupling chemistry reproducible. Downstream, D-asparagine-containing peptidomimetics serve as stereodefined research materials and synthetic intermediates for SAR mapping, fragment-to-lead optimization, and iterative scaffold refinement in medicinal chemistry programs.
5. Pharmaceutical Manufacturing
N-α-Fmoc-D-asparagine is relevant to pharmaceutical manufacturing and fine chemical production contexts that require reproducible synthesis of protected amino acid building blocks for peptide-based intermediates. The robust Fmoc chemistry supports standard peptide synthesis compatibility, where controlled deprotection and coupling can be integrated into manufacturing-scale peptide assembly routes for stereochemically defined intermediates. The presence of an unprotected side-chain carboxamide reduces the need for additional side-chain protection in many workflows, simplifying protection/deprotection planning for asparagine-containing sequences. Downstream utility includes preparation of protected D-asparagine peptide fragments and stereodefined intermediates that can feed into further purification, conversion to final peptide forms, and manufacturing-oriented process development for specialty chemical production.
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