Boc-D-Glu(OtBu)-ONp is a protected, amino-acid derivative based on D-glutamic acid in which the α-amino group is protected as a Boc carbamate and the side-chain γ-carboxyl is protected as a tert-butyl ester. The molecule bears a carboxylate functionality converted to an ONp (p-nitrophenyl) ester, providing an activated acyl group, while the D stereochemical configuration is indicated by the "D" designation and the tert-butyl group masks the side-chain carboxyl from undesired reactions. This ONp ester is employed as an acylating intermediate for peptide synthesis and for preparing more complex glutamate-containing amino acid derivatives under conditions that take advantage of the activated ester for controlled coupling.
CAT No: CP26653
CAS No:200397-60-0
Synonyms/Alias:BOC-D-GLU(OTBU)-ONP;200397-60-0;Boc-D-glutamicacidgamma-tert-butylester-4alpha-nitrophenylester;C20H28N2O8;AC1OLR9N;BOC-D-GLU-ONP;CTK8E9768;ZINC4899647;6326AH;RT-011731;K-5861;5-O-tert-butyl1-O-(4-nitrophenyl)(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
Boc-D-Glu(OtBu)-ONp is a D-configured glutamic acid derivative supplied as an ONp ester, combining a Boc-protected α-amino group with an OtBu-protected side-chain carboxylate. This protected, activated form is designed for peptide chemistry workflows where controlled coupling of the glutamate side chain is required, while minimizing side reactions from free carboxyl functionality. The ONp ester activation enables efficient formation of amide bonds under standard peptide intermediate handling conditions, making it a widely used building block for assembling glutamate-containing sequences and related protected intermediates.
1. Peptide Coupling Building Block
Boc-D-Glu(OtBu)-ONp is used by peptide synthesis groups to introduce a D-glutamate residue with orthogonally protected side-chain functionality. The Boc group provides robust protection of the α-amino functionality during fragment coupling steps, while the OtBu group keeps the side-chain carboxyl protected to prevent undesired crosslinking or branching reactions. The ONp ester activation is particularly valued in workflows that require reliable amide bond formation from glutamate-derived activated intermediates, supporting the assembly of protected peptide segments that later undergo deprotection and further elongation.
2. D-Glutamate Peptide Analog Synthesis
Boc-D-Glu(OtBu)-ONp supports the preparation of D-glutamate-containing peptide analogs used in structure-activity relationship studies, peptide stability investigations, and stereochemical control of peptide conformation. Research teams working on non-proteinogenic or stereochemically defined peptide constructs often select this type of activated, protected glutamate derivative to maintain side-chain protection throughout synthesis and to ensure that the D-stereocenter is preserved until final processing. Downstream, the resulting protected intermediates can be carried into further coupling steps to generate peptide libraries with defined glutamate stereochemistry and side-chain carboxyl availability after deprotection.
3. Protected Glutamate Intermediate Development
Boc-D-Glu(OtBu)-ONp is frequently used in pharmaceutical intermediate development and specialty chemical manufacturing to generate glutamate-derived protected intermediates that can be carried into subsequent derivatization. The combination of Boc and OtBu protection with an activated ONp ester provides a practical platform for preparing well-defined amide-forming intermediates without exposing reactive carboxyl groups prematurely. Process chemists and custom synthesis teams value this building block for controlled, stepwise construction of glutamate-containing motifs, where consistent protection patterns and activated functionality help streamline downstream assembly into larger protected structures.
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