Fmoc-Glu-OFm is an Fmoc-protected glutamic acid derivative in which the α-amino group is masked by the fluorenylmethoxycarbonyl (Fmoc) protecting group and the side-chain carboxyl is esterified as an OFm group. The molecule contains a protected amino functionality, a free carboxyl group at the α-position (as indicated by the glutamate framework), and an additional esterified carboxyl on the side chain, with stereochemistry consistent with the glutamic acid backbone as implied by the name. Fmoc-Glu-OFm is used as a protected amino acid building block for peptide synthesis and related peptide-derivative preparation, where orthogonal protection and esterification help control chemoselectivity during stepwise assembly and side-chain functional-group handling.
CAT No: CP26655
CAS No:200616-18-8
Synonyms/Alias:Fmoc-Glu-OFm;200616-18-8;(S)-5-((9H-Fluoren-9-yl)methoxy)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-oxopentanoicacid;SCHEMBL4300738;MolPort-020-003-927;ZINC2560902;AKOS016000579;AK119011;KB-211577;N-(9H-Fluorene-9-ylmethoxycarbonyl)-L-glutamicacid1-(9H-fluorene-9-yl)methylester
Fmoc-Glu-OFm is an Fmoc-protected glutamic acid derivative in which the α-amino group is masked by the fluorenylmethoxycarbonyl (Fmoc) protecting group and the side-chain carboxyl is present as an Fm ester (OFm). The molecule therefore contains a stereodefined chiral α-center typical of L-glutamate chemistry, along with two carboxyl-derived functional handles that can be selectively unmasked under orthogonal deprotection conditions. The Fmoc carbamate and Fm ester exhibit distinct stability profiles, enabling controlled progression from protected amino acid building block handling to sequential peptide coupling and side-chain functionalization. The resulting structure supports peptide synthesis compatibility through N-Fmoc deprotection and provides a protected side-chain carboxyl that can be converted into amide, ester, or other glutamate-derived functionalities for downstream synthetic and biochemical studies.
1. Peptide Synthesis
Fmoc-Glu-OFm is used in peptide building block preparation for solid-phase peptide synthesis and related coupling workflows where orthogonal protection of the α-amino and side-chain carboxyl is required. The Fmoc group supports standard base-mediated removal to generate a reactive N-terminus for peptide coupling, while the side-chain Fm ester can remain masked during early chain assembly to prevent undesired side reactions. The glutamate backbone geometry and stereochemistry align with conventional amino acid coupling chemistries, allowing incorporation of a protected glutamic acid residue into peptides and peptide fragments. The protected side-chain carboxyl can be unmasked after assembly to enable formation of side-chain amides, linkers, or charged motifs that influence peptide conformation and recognition. Fmoc-Glu-OFm thus functions as a practical intermediate for constructing peptide sequences containing controlled glutamate functionality.
2. Side-Chain Functionalization
Fmoc-Glu-OFm serves amino acid derivatization and side-chain modification programs by providing a protected glutamate carboxyl group that can be selectively transformed after N-Fmoc deprotection and peptide or scaffold assembly. The Fm ester on the side-chain carboxyl allows controlled conversion into activated carboxylic acid forms for amide bond formation, esterification, or coupling to nucleophiles used in linker installation. The presence of the chiral α-center ensures stereochemical integrity of the glutamate residue when generating derivatives for structure-activity relationship studies and molecular recognition experiments. Side-chain unmasking can be applied to introduce negative charge, polarity, or conjugation handles while maintaining the peptide-compatible backbone. Fmoc-Glu-OFm therefore supports downstream generation of glutamate-containing analogs used in synthetic organic chemistry and biochemical research intermediate preparation.
3. Bioconjugation Chemistry
Fmoc-Glu-OFm can be applied to bioconjugation chemistry workflows that require glutamate-derived carboxyl functionality for controlled attachment of biomolecule-reactive groups. The protected side-chain carboxyl provides a handle that can be unmasked to yield a carboxylic acid suitable for coupling to amines, hydrazides, or other nucleophiles depending on the conjugation strategy. The Fmoc-protected α-amino group enables integration into peptide-based conjugates where sequential deprotection and coupling can be used to control attachment sites and preserve defined stereochemistry. The resulting glutamate-containing conjugation intermediates can be used to generate peptide linkers, scaffolded probes, or functionalized biomolecule modifiers for chemical biology investigations. Fmoc-Glu-OFm thus supports synthetic routes that connect amino acid chemistry to biomolecule labeling and targeted molecular construction.
4. Process Chemistry Intermediate
Fmoc-Glu-OFm is relevant to process chemistry and fine chemical synthesis as a protected amino acid intermediate designed for reproducible protection-group behavior across multi-step manufacturing sequences. The orthogonality between the Fmoc carbamate and the Fm ester enables stepwise deprotection and functional conversion without requiring full exposure of both carboxyl-derived groups at once. The glutamate-derived protected carboxyl motif can be carried through coupling operations, reducing the risk of uncontrolled side reactions and enabling controlled downstream formation of carboxylic acid derivatives or activated intermediates. The stereodefined α-center supports consistent product identity in peptide building block supply chains where chiral integrity is required. Fmoc-Glu-OFm can therefore be incorporated into scalable synthetic routes for peptide reagents, specialty chemical production, and industrial intermediate preparation where protection strategy is a key determinant of manufacturability.
5. Analytical Reference Standards
Fmoc-Glu-OFm is suitable for analytical research and method development where defined, protected glutamate standards support characterization of peptide synthesis intermediates and deprotection outcomes. The combination of an Fmoc-protected amino group and an Fm-protected side-chain ester provides distinguishable chemical features that can be monitored by chromatographic and spectrometric techniques during synthetic workflows. The presence of a stereodefined glutamate residue enables assignment of identity for chiral amino acid derivative series used in quality control of protected amino acid synthesis and peptide building block preparation. The compound's functional group pattern can also serve as a reference for evaluating side-chain stability during coupling steps and for confirming selective conversion after deprotection. Fmoc-Glu-OFm thus supports analytical verification tasks that connect amino acid protection chemistry to reliable peptide science operations.
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