Fmoc-D-Glu(All)-OH is an Fmoc-protected, D-configured glutamic acid derivative bearing an Alloc (allyloxycarbonyl) protecting group on the side-chain carboxyl group, with the amino acid backbone presented as a free C-terminal carboxylic acid (-CO2H). The molecule contains an Fmoc carbamate on the α-amino group and an Alloc-protected γ-carboxyl side chain, providing orthogonal protection that can control chemoselectivity during stepwise peptide assembly while maintaining the stereochemical identity implied by the D designation. In peptide chemistry, it is employed as a protected glutamate building block for incorporating a glutamic acid residue with a selectively addressable side chain, supporting synthesis of peptides and peptide-derived conjugates where side-chain deprotection and functionalization are performed under controlled conditions.
CAT No: CP25585
CAS No:204251-33-2
Synonyms/Alias:Fmoc-d-glu(oall)-oh;204251-33-2;MolPort-008-267-641;ZINC2572446;FT-0697976;V4218
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-glutamic-acid-gamma allyl ester
Fmoc-D-Glu(All)-OH is an Fmoc-protected D-glutamic acid derivative bearing an allyl ester on the side-chain carboxyl group, providing a stereodefined amino acid building block for peptide chemistry. The molecule contains the chiral glutamate backbone (D-configuration at the alpha carbon), a carbamate-protected alpha-amino group (Fmoc), and a free C-terminal carboxylic acid for coupling, while the side-chain functionality is masked as an allyl ester that can be selectively transformed. The allyl ester and carboxylic acid enable controlled orthogonal reactivity, allowing side-chain deprotection or functional group conversion without disturbing the Fmoc group under standard peptide synthesis conditions. The combination of an Fmoc-protected stereogenic amino acid and an orthogonally removable allyl ester makes Fmoc-D-Glu(All)-OH a practical chiral intermediate for constructing D-glutamate-containing sequences and for downstream derivatization of glutamate side chains.
1. Peptide Synthesis
Fmoc-D-Glu(All)-OH serves as an Fmoc-compatible peptide building block for solid-phase peptide synthesis where the D-glutamate stereochemistry is required for conformational control and protease resistance in peptide analogs. The Fmoc carbamate protects the alpha-amino group during chain assembly, while the free C-terminal carboxylic acid participates in standard peptide coupling chemistry to extend the growing peptide. The allyl-protected side-chain carboxyl group provides orthogonal protection, supporting sequential deprotection or side-chain functionalization after the peptide backbone is assembled. The resulting D-glutamate-containing peptides can be used as research-grade constructs for studying sequence effects, stability, and side-chain-dependent recognition in peptide science and chemical biology.
2. Side-Chain Functionalization
Fmoc-D-Glu(All)-OH supports amino acid derivatization workflows that target glutamate side-chain modification through the orthogonal allyl ester handle. The allyl ester can be converted into alternative side-chain functionalities after peptide or intermediate preparation, enabling access to glutamate derivatives such as free carboxylic acid forms, activated acid variants, or side-chain functional groups suitable for further coupling chemistry. The presence of a stereodefined D-glutamate backbone helps maintain chiral integrity during downstream transformations, which is relevant for stereochemically controlled SAR studies and molecular design. The compound's protected-group pattern aligns with synthetic organic chemistry strategies that require selective functional group interconversions while preserving the peptide-compatible Fmoc protection logic.
3. Peptidomimetics And SAR
Fmoc-D-Glu(All)-OH can be employed in peptidomimetic construction where D-glutamate incorporation and side-chain carboxyl manipulation are used to tune binding, conformation, and physicochemical properties of bioactive scaffolds. The allyl-protected side-chain carboxyl group allows late-stage modification, supporting structure-activity relationship studies that compare analogs with different side-chain chemistries while keeping the backbone stereochemistry constant. The Fmoc-protected alpha-amino group enables systematic assembly of analog series using consistent coupling and deprotection cycles, which is useful for generating libraries of stereodefined glutamate-containing fragments. Downstream derivatives prepared from Fmoc-D-Glu(All)-OH can feed into fragment-based molecular design and SAR workflows that rely on controlled stereochemical presentation of acidic side chains.
4. Chemical Biology Labeling
Fmoc-D-Glu(All)-OH is suitable for chemical biology research requiring stereospecific incorporation of D-glutamate residues into peptide probes and conjugatable biomolecules. The allyl ester side-chain protection provides a handle for orthogonal chemical modification after conjugation or probe assembly, enabling controlled generation of carboxylate-bearing motifs for subsequent coupling to linkers, tags, or affinity reagents. The Fmoc group supports reliable peptide assembly into defined probe architectures, while the D-configuration can help modulate stability and reduce unwanted enzymatic processing in labeling experiments. The resulting labeled or conjugatable constructs can be used as tools for investigating molecular recognition, binding-site mapping, and biomolecular interaction dynamics.
5. Pharmaceutical Intermediate Preparation
Fmoc-D-Glu(All)-OH can function as a chiral amino acid intermediate for manufacturing-oriented synthesis of protected glutamate derivatives used in drug discovery and pharmaceutical intermediate supply chains. The molecule's protected alpha-amino group (Fmoc) and orthogonally protected side-chain ester (allyl) provide a controlled protection strategy that supports stepwise synthesis of complex, stereodefined intermediates. The free C-terminal carboxylic acid enables downstream conversion into activated forms for coupling steps in intermediate fabrication, including the preparation of peptidic or peptidomimetic fragments. The structural design aligns with process chemistry needs for predictable deprotection and functional group transformation sequences when preparing stereochemically defined glutamate-containing building blocks at scale.
6. Analytical Standards
Fmoc-D-Glu(All)-OH can be applied to analytical research as a reference material for method development involving Fmoc-based amino acid derivatives and D-glutamate-containing peptides. The distinct combination of Fmoc chromophore and allyl ester functionality supports traceable detection and characterization by chromatographic and spectrometric techniques, aiding identification of protected amino acid species and monitoring of deprotection or side-chain conversion steps. The stereodefined D-glutamate backbone helps distinguish stereoisomeric behavior from L-analog standards in analytical workflows. The compound can therefore serve as a chemically defined standard for verifying peptide coupling outcomes, protecting-group integrity, and side-chain modification states in amino acid chemistry and peptide process monitoring.
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