Fmoc-D-Asp-NH2 is a protected amino acid derivative based on D-aspartic acid in which the α-amino group is converted to a carboxamide (-NH2) and the α-carboxyl functionality is protected as an Fmoc carbamate. The molecule contains a side-chain carboxylic acid characteristic of Asp, providing a polar, ionizable functionality for salt formation and hydrogen-bonding interactions, while the Fmoc group introduces a base-labile protecting group that controls chemoselectivity during stepwise peptide assembly. Fmoc-D-Asp-NH2 is used as a building block for solid-phase peptide synthesis and related peptide chemistry workflows where the protected amino acid form supports controlled coupling and subsequent deprotection to generate peptide-bound Asp residues.
CAT No: CP25554
CAS No:200335-41-7
Synonyms/Alias:Fmoc-D-asparticacidalpha-amide;200335-41-7;FMOC-D-ASP-NH2;CTK8F0653;MolPort-020-003-913;ZINC2560803;Fmoc-D-Isoasn-OH,Fmoc-D-isoasparagine;RT-012928
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-aspartic-acid amide
Fmoc-D-Asp-NH2 is a stereochemically defined D-configured aspartamide bearing a fluorenylmethoxycarbonyl (Fmoc) group on the α-amino functionality and a free primary amide at the β-carboxyl position (side chain aspartamide). The molecule combines a protected, base-labile Fmoc carbamate for orthogonal peptide synthesis with an unprotected carboxamide side chain that can participate in hydrogen-bonding and polarity-driven molecular recognition. The D stereocenter at the α-position supports incorporation of a non-proteinogenic stereochemical element into peptides and peptide-like frameworks, enabling control over backbone conformation and side-chain orientation. The presence of both the Fmoc-protected nitrogen and the side-chain amide makes the compound a practical chiral building block for protected amino acid chemistry and downstream derivatization into amide-linked intermediates.
1. Peptide Synthesis
Fmoc-D-Asp-NH2 is used in solid-phase peptide synthesis and related coupling workflows as an Fmoc-protected amino acid amide building block. The Fmoc group enables stepwise N-terminal deprotection under base-mediated conditions, while the D-aspartamide side chain provides an additional hydrogen-bonding functional handle without requiring side-chain carboxyl activation. The β-amide functionality can be retained through peptide assembly, supporting peptide coupling chemistry that targets the α-amino group while preserving side-chain integrity. The resulting D-Asp-NH2 incorporation is useful for generating peptides with altered stereochemistry, improved resistance to certain proteolytic pathways, or modified binding interactions in structure-activity relationship studies. Fmoc-D-Asp-NH2 therefore serves as a defined stereochemical unit for constructing peptide analogs and amide-rich sequences in synthetic peptide science.
2. Unnatural Amino Acid Incorporation
Fmoc-D-Asp-NH2 supports chemical biology and peptide engineering efforts that require stereochemical inversion relative to canonical L-aspartate. The D configuration at the α-carbon, together with the side-chain carboxamide, enables systematic exploration of how backbone stereochemistry and side-chain amide polarity influence conformational preference and receptor or enzyme recognition. The Fmoc-protected amine facilitates standard peptide coupling strategies, allowing incorporation into larger peptide scaffolds without changing the synthesis logic for neighboring residues. The side-chain amide can participate in specific intermolecular interactions and can be used as a stable functional mimic of carboxyl-derived motifs in peptidomimetics. This makes Fmoc-D-Asp-NH2 a practical chiral amino acid intermediate for unnatural amino acid incorporation and stereocontrolled scaffold design.
3. Bioconjugation Chemistry
Fmoc-D-Asp-NH2 can be applied to bioconjugation and biomolecule modification strategies where amide-bearing amino acid residues are introduced as defined linkers or recognition elements. The compound's protected α-amino functionality allows controlled generation of a reactive amino terminus after Fmoc removal, enabling subsequent coupling to activated carboxyl groups on proteins, polymers, or targeting ligands. The side-chain carboxamide provides a polar, hydrogen-bond-capable group that can influence local solvation and reduce nonspecific hydrophobic interactions during conjugate formation. The D stereochemistry can be used to tune the stability and conformational behavior of the conjugate, including in peptide-tagged biomolecules. Fmoc-D-Asp-NH2 thus functions as a stereodefined amino acid derivative for constructing amide-rich conjugation motifs used in chemical biology workflows.
4. Peptidomimetics And SAR Studies
Fmoc-D-Asp-NH2 is suitable for peptidomimetic construction and structure-activity relationship studies that require precise control over functional group placement and stereochemistry. The Fmoc-protected nitrogen supports iterative assembly of peptide-like sequences, while the side-chain amide provides a persistent polar group that can mimic hydrogen-bond donors/acceptors associated with aspartate-derived pharmacophores. The D configuration enables SAR exploration of stereochemical determinants by comparing analogs that differ only in α-stereochemistry while maintaining the same side-chain functional identity. The amide side chain can also serve as a platform for further synthetic transformations, such as conversion to alternative amide or urea-like functionalities in downstream intermediate preparation when orthogonal chemistries are chosen. Fmoc-D-Asp-NH2 therefore helps generate stereochemically defined analog series for medicinal chemistry and molecular design programs focused on binding-site interaction mapping.
5. Process Chemistry Intermediate
Fmoc-D-Asp-NH2 is used as a chiral amino acid derivative intermediate in fine chemical synthesis and process chemistry settings where protected amino acids must be handled with predictable deprotection behavior. The Fmoc carbamate provides a robust protection strategy for the α-amino group during coupling and purification steps, while the side-chain carboxamide remains chemically stable under typical peptide synthesis conditions. The defined D stereocenter supports reproducible incorporation into downstream peptide building blocks, including for manufacturing of peptide reagents, reference standards, and peptide-based materials. The compound's functional group set supports scalable conversion into other amide-containing intermediates through selective activation of the α-amino position after Fmoc removal or through side-chain-directed derivatization strategies. Fmoc-D-Asp-NH2 thus aligns with industrial intermediate preparation needs that prioritize stereochemical integrity and orthogonal protection for reliable downstream synthesis.
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