Fmoc-D-Gla(OtBu)2-OH is an Fmoc-protected D-form amino acid derivative of glutamic acid bearing two tert-butyl ester groups on the side-chain carboxylates, classifying it as a protected, non-free amino acid suitable for peptide chemistry. The molecule contains an Fmoc carbamate on the amino group and a free carboxylic acid at the α-position while the side-chain termini are masked as tert-butyl esters, providing controlled chemoselectivity toward side-chain carboxyl reactivity during stepwise coupling. In synthesis workflows such as solid-phase peptide synthesis, it functions as a protected glutamate building block for preparing peptides that incorporate a D-configured glutamic acid residue with carboxyl groups that remain protected until later deprotection steps.
CAT No: CP25162
CAS No:111662-65-8
Synonyms/Alias:Fmoc-D-Gla(otbu)2-OH;111662-65-8;Fmoc-d-gla(otbu)2-oh;AmbotzFAA1321;SCHEMBL15630864;MolPort-006-705-689;ZINC22059631;AKOS015910199;FT-0679784;I14-39530;I14-40703;(2R)-5-(tert-butoxy)-4-(tert-butoxycarbonyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-oxopentanoicacid
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-gamma-Carboxy-D-glutamic-acid-gamma-di-t-butyl ester
Fmoc-D-Gla(OtBu)2-OH is a D-configured glutamic acid derivative bearing an Fmoc-protecting group on the α-amino function and two tert-butyl ester protections on the side-chain carboxylates, giving a protected amino acid building block with masked acidic functionality. The molecule contains a chiral center at the α-position and a second stereochemical element associated with the D-glutamate framework, while the Fmoc carbamate and tert-butyl ester groups establish orthogonal protection behavior for stepwise peptide assembly. The side-chain diester pattern tunes solubility and suppresses undesired side reactions during coupling, while the Fmoc group enables base-mediated deprotection to reveal a reactive amine for iterative chain elongation. As a protected amino acid intermediate, Fmoc-D-Gla(OtBu)2-OH participates in standard peptide synthesis chemistry and can be converted downstream into free diacids or selectively functionalized glutamate analogs for biochemical and materials-oriented research.
1. Peptide Synthesis
Fmoc-D-Gla(OtBu)2-OH is used in peptide synthesis workflows where a D-glutamate residue with protected side-chain carboxylates is required for controlled coupling chemistry. The Fmoc carbamate on the α-amine supports iterative solid-phase or solution-phase assembly, while the two tert-butyl ester groups keep the side-chain carboxylates inert toward coupling reagents and minimize cross-reactivity. Base-triggered Fmoc removal generates the nucleophilic amine for amide bond formation, and subsequent acidolysis can unmask both side-chain carboxylates to yield a D-configured glutamate segment within the final peptide. Downstream peptide analogs prepared from this building block can be applied to backbone stereochemistry studies, stability-focused peptide design, and sequence-specific synthesis of glutamate-containing motifs.
2. Peptidomimetics And SAR Studies
Fmoc-D-Gla(OtBu)2-OH serves as a chiral precursor for peptidomimetic construction and structure-activity relationship studies that require glutamate-like side-chain geometry with stereochemical control. The di-protected side-chain carboxylate functionality can be retained during scaffold assembly and later transformed into free diacids or activated derivatives, enabling systematic variation of charge distribution and hydrogen-bonding patterns in analog libraries. The D-configuration supports incorporation of non-native stereochemistry that can modulate conformational preferences and protease resistance in peptide-like frameworks. Resulting D-glutamate-containing mimetics can be used to generate structure-defined analog sets for SAR investigations and molecular recognition studies.
3. Chemical Biology Conjugation
Fmoc-D-Gla(OtBu)2-OH can be applied in chemical biology and biomolecule modification strategies where glutamate-derived linkers or charged handles are incorporated into conjugates. The protected amino acid form allows stepwise assembly of peptide linkers with defined stereochemistry, and the orthogonal protection scheme supports selective deprotection to reveal either the α-amine during coupling or the side-chain diacids for subsequent activation. tert-Butyl ester deprotection can generate a diacid motif suitable for amide coupling, esterification, or formation of activated intermediates for conjugation to amines or alcohol-containing biomolecules. D-glutamate-bearing conjugation scaffolds may be used to tune solubility, introduce defined acidic spacing, and support reproducible attachment geometries in labeling and probe development.
4. Process Chemistry Intermediate
Fmoc-D-Gla(OtBu)2-OH functions as a practical process chemistry intermediate for manufacturing peptide building blocks and protected amino acid derivatives at scale. The Fmoc group provides a robust, commercially common protecting strategy for handling and storage, while the tert-butyl ester protections on both side-chain carboxylates reduce side reactions associated with free acids during coupling and purification steps. The compound's protected, neutralized form can be engineered into manufacturing routes that emphasize controlled deprotection events, first removing Fmoc under basic conditions and then unmasking the diacid under acidic conditions when required. Downstream production of D-glutamate-containing peptides, activated glutamate derivatives, and stereochemically defined intermediates can be supported by this orthogonally protected design.
5. Analytical Reference Standards
Fmoc-D-Gla(OtBu)2-OH is suitable for analytical research as a stereochemically defined protected glutamate reference material and method development component. The presence of both Fmoc and tert-butyl ester groups creates characteristic ionization and fragmentation behavior that can aid LC-MS or MS/MS method tuning for protected amino acid derivatives and peptide fragments. The D-configuration and protected diacid pattern support unambiguous tracking of glutamate incorporation during synthesis and can help validate deprotection completeness when monitoring conversion to diacid-containing products. Analytical standards derived from this building block can support quality control, impurity profiling, and characterization of peptide synthesis intermediates in research and industrial settings.
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