Fmoc-D-glutamic acid γ-tert.butylester monohydrate is a protected, derivatized amino acid in which glutamic acid bears an Fmoc group on the α-amino functionality and a γ-tert-butyl ester on the side-chain carboxyl group, with D stereochemistry indicated by the product name. The molecule contains a free α-carboxylic acid and a γ-carboxyl group masked as a tert-butyl ester, while the Fmoc carbamate and the tert-butyl ester act as protecting groups that control chemoselectivity during peptide-coupling steps and reduce side reactions from the carboxyl functionalities. As a solid-phase or solution-phase peptide synthesis intermediate, it provides a protected glutamate building block suitable for stepwise incorporation of a glutamic acid residue and for preparing glutamate-containing peptide derivatives where side-chain carboxyl protection is maintained until deprotection.
CAT No: CP00735
Fmoc-D-glutamic acid γ-tert.butylester monohydrate is a D-configured glutamate derivative in which the α-amino group is protected as the Fmoc carbamate and the γ-carboxyl functionality is masked as a tert-butyl ester, with crystallization as a monohydrate. The molecule therefore presents a protected amino acid backbone for controlled peptide coupling while retaining a stereogenic center at the α-carbon that supports stereochemically defined incorporation into peptide sequences. The Fmoc group enables base-mediated deprotection to reveal an aniline-like carbamate-free amine for stepwise solid-phase or solution-phase assembly, whereas the tert-butyl ester can be removed under acid to regenerate the γ-carboxylic acid for subsequent functionalization. The presence of the monohydrate can influence handling and dissolution behavior, and the protected functional-group pattern supports downstream conversion into side-chain carboxylate-bearing glutamate analogs and other glutamate-derived intermediates.
1. Peptide Synthesis
Fmoc-D-glutamic acid γ-tert.butylester monohydrate is used in peptide building-block preparation for both solid-phase and solution-phase peptide synthesis where stereodefined D-glutamate residues are required. The Fmoc-protected α-amine participates in standard peptide coupling chemistry after Fmoc removal, while the γ-tert-butyl ester protects the side-chain carboxyl from undesired acylation during chain elongation. The orthogonal protection pattern supports sequential deprotection strategies, enabling controlled exposure of the side-chain carboxyl for late-stage modifications such as salt formation, side-chain amidation, or ester-to-acid transformations. The resulting D-glutamate-containing peptides and peptide fragments can be generated for structural studies, peptide analog construction, and stereochemical control in synthetic peptide libraries.
2. Side-Chain Functionalization
Fmoc-D-glutamic acid γ-tert.butylester monohydrate supports side-chain functionalization workflows that rely on orthogonal protection of the γ-carboxyl group. The tert-butyl ester masking enables selective regeneration of the γ-carboxylic acid under conditions compatible with the Fmoc strategy, allowing subsequent derivatization into amides, activated esters, or carboxylate salts for conjugation chemistry. The D-stereochemistry can be leveraged to tune molecular recognition and protease stability in peptide-based constructs, where side-chain geometry and stereochemical identity influence binding and processing. Downstream products include functionalized glutamate derivatives used as intermediates for bioconjugation handles, peptidomimetic scaffolds, and chemically defined reference materials.
3. Protected Amino Acids
Fmoc-D-glutamic acid γ-tert.butylester monohydrate serves as a protected amino acid intermediate in synthetic organic chemistry where controlled deprotection and selective reactivity are required. The Fmoc carbamate provides a robust N-protection strategy that is stable under many coupling conditions yet removable under base to generate the free amine for peptide bond formation. The γ-tert-butyl ester functions as a second orthogonal protecting group, allowing chemoselective side-chain exposure for further transformations without perturbing the α-amino functionality during intermediate handling. The monohydrate form is relevant for reproducible processing in chemical manufacturing and research-scale synthesis, supporting consistent preparation of D-glutamate-containing intermediates used in fine chemical synthesis and peptide chemistry.
4. Drug Discovery
Fmoc-D-glutamic acid γ-tert.butylester monohydrate can be applied to drug discovery programs that require stereochemically defined peptidomimetic fragments and constrained amino acid motifs. The combination of Fmoc-protected α-amine and protected γ-carboxyl enables incorporation into peptide-like scaffolds during library synthesis, while the D-configuration supports exploration of stereochemical effects on target binding and metabolic stability. Side-chain carboxyl regeneration after deprotection can be used to introduce polar functionalities, form salt bridges, or generate conjugation-ready groups for fragment linking and SAR-focused analog generation. The compound therefore functions as a synthetic intermediate for constructing structure-defined molecules used in medicinal chemistry exploration and analytical reference preparation.
5. Pharmaceutical Manufacturing
Fmoc-D-glutamic acid γ-tert.butylester monohydrate is suitable for pharmaceutical manufacturing workflows that involve controlled peptide intermediate preparation and protected amino acid handling. The orthogonal N- and side-chain protection pattern supports manufacturing-compatible sequences where Fmoc removal and tert-butyl ester deprotection can be orchestrated to minimize side reactions and maintain stereochemical integrity of the D-glutamate residue. The protected functional groups enable predictable downstream transformations into carboxylate-bearing intermediates used for further conjugation, salt formation, or conversion into activated derivatives during process development. The compound's role as a chiral, protected glutamate building block aligns with industrial fine chemical synthesis needs for reproducible intermediate generation and scalable peptide-derivative construction.
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