Fmoc-D-Asp-OFm is a protected amino acid derivative in which the D-form of aspartic acid is functionalized at the α-amino group with an Fmoc carbamate and at the side-chain carboxyl group as an OFm ester. The molecule contains an Fmoc-protected nitrogen, a free α-carboxyl group, and a side-chain carboxyl masked as an O-formyl (Fm) ester, providing controlled chemoselectivity by suppressing undesired side reactions from the acidic side chain while maintaining the amino acid backbone for coupling. In peptide chemistry and solid-phase peptide synthesis workflows, it functions as a stepwise building block for introducing a D-aspartate residue with orthogonal side-chain protection suitable for subsequent selective deprotection and derivatization.
CAT No: CP26786
CAS No:214852-35-4
Synonyms/Alias:Fmoc-D-Asp-OFm;ZINC2569790;214852-35-4
Fmoc-D-Asp-OFm is an Fmoc-protected D-aspartic acid derivative bearing an esterified side chain as an OFm (Fm) group, providing a carboxylate-equivalent functionality masked as a stable protecting group while retaining the stereodefined α-amino acid core. The molecule contains an Fmoc carbamate on the α-amine for orthogonal protection in solid-phase or solution peptide synthesis, along with a free α-carboxylate as part of the aspartate framework and a side-chain carboxyl functionality converted to an Fm ester. The D-configuration at the α-carbon supports stereochemical control for peptide backbone incorporation and for generating aspartate stereoisomers in structure-activity relationship studies. The combination of Fmoc and side-chain ester protection enables controlled deprotection sequences and downstream transformation of the side-chain carboxyl group into amides, esters, or activated carboxylates for further derivatization.
1. Peptide Synthesis
Fmoc-D-Asp-OFm is a protected amino acid building block suited for peptide coupling workflows where orthogonal protection is required for aspartate side-chain handling. The Fmoc group on the α-amine supports standard N-terminal activation and coupling chemistry after deprotection, while the OFm side-chain ester masks the aspartate carboxylate to prevent side reactions during chain assembly. The D-stereochemistry enables incorporation of the D-aspartate configuration into peptide sequences, supporting studies of stereochemical effects on folding, stability, and binding. The protected side-chain carboxyl functionality can be unveiled or converted under appropriate conditions to generate peptide analogs with defined side-chain modifications for downstream characterization.
2. Peptidomimetics And SAR
Fmoc-D-Asp-OFm is applicable to peptidomimetic and medicinal chemistry programs that require controlled introduction of D-aspartate residues into constrained scaffolds. The aspartate side-chain ester protection allows stepwise construction of analog libraries where side-chain carboxyl reactivity is held in reserve until late-stage derivatization. The presence of an Fmoc-protected α-amino group supports iterative fragment coupling to generate peptide-like backbones that retain stereochemical definition at the chiral center. The resulting intermediates can be converted into amide, ester, or carboxylate-based motifs to probe structure-activity relationship trends driven by side-chain charge, hydrogen-bonding patterns, and stereochemical inversion.
3. Side-Chain Functionalization
Fmoc-D-Asp-OFm is suitable for amino acid derivatization strategies targeting aspartate side-chain chemistry while maintaining compatibility with peptide-grade protection patterns. The OFm ester masks the side-chain carboxyl group during synthetic manipulations, reducing undesired acylation or salt formation when forming new bonds elsewhere in the molecule. The Fmoc carbamate enables controlled N-deprotection to expose an amine for subsequent coupling or conjugation steps, while the D-aspartate configuration preserves stereochemical integrity of the backbone. The compound can serve as a controlled precursor for generating derivatives bearing activated carboxylates, amide linkages, or side-chain conjugation handles used in chemical biology probes and scaffold diversification.
4. Chemical Biology Probes
Fmoc-D-Asp-OFm can be employed in chemical biology research where stereodefined aspartate residues are incorporated into labeled peptides or recognition elements. The protected α-amino group and masked side-chain carboxyl functionality support sequential assembly of probe backbones with minimized cross-reactivity during labeling workflows. The D-configuration supports probe designs that test stereochemical requirements for molecular recognition, enzyme tolerance, or receptor-like interactions without assuming a specific biological outcome. The orthogonally protected architecture facilitates downstream conversion of the side-chain carboxyl group into conjugation-ready forms for attaching tags, linkers, or affinity motifs while maintaining peptide synthesis compatibility.
5. Pharmaceutical Intermediate Preparation
Fmoc-D-Asp-OFm is relevant to pharmaceutical manufacturing and fine chemical synthesis as a chiral, protected amino acid intermediate for producing aspartate-containing peptide intermediates and related carboxyl-functionalized fragments. The Fmoc-protected amine and OFm side-chain ester provide a protection strategy that can be integrated into controlled manufacturing routes where selective deprotection and subsequent coupling steps are required to manage functional group reactivity. The stereodefined D-aspartate center supports consistent generation of stereochemically pure intermediates used in the synthesis of peptide analogs and carboxyl-bearing building blocks. The compound's protected functional groups enable downstream transformations into activated carboxyl derivatives suitable for further synthesis steps in applied product development pipelines.
6. Process Chemistry Intermediate
Fmoc-D-Asp-OFm is suitable for process chemistry applications that require robust, isolable protected amino acid derivatives for scale-up-compatible peptide construction. The dual protection pattern, with an Fmoc carbamate and an OFm side-chain ester, supports a controlled sequence of deprotection and coupling operations by separating amine unmasking from side-chain carboxyl activation timing. The D-aspartate stereocenter helps ensure stereochemical fidelity across synthetic stages, which is important for reproducible intermediate profiles in manufacturing workflows. The compound can be integrated as a defined amino acid feedstock for producing protected peptide fragments and for generating consistent downstream derivatives used in specialty chemical production and industrial peptide chemistry.
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