Boc-D-Asp(OtBu)-OH · DCHA is a protected, stereochemically defined amino acid derivative in which the D-configuration of the aspartic acid backbone is retained while the α-amino group is masked as a Boc carbamate and the side-chain carboxyl group is protected as a tert-butyl ester (Asp(OtBu)). The molecule contains the Boc-protected amino functionality and two carboxyl-derived groups that are differentially protected, with DCHA indicating formation of a dicyclohexylamine salt that can influence solid-state handling and solubility for synthesis and characterization. In peptide chemistry, this protected aspartate analogue is used as a stepwise building block for controlled chemoselective coupling, where Boc deprotection and side-chain ester stability support preparation of aspartyl-containing peptides and aspartate-based conjugates for structure-activity studies and analytical method development.
CAT No: CP26642
CAS No:200334-95-8
Synonyms/Alias:200334-95-8;Boc-D-Asp(OtBu)-OHDCHA;Dicyclohexylamine(R)-4-(tert-butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate;Boc-D-Asp(OtBu)-OHinvertedexclamationmarkcurrencyDCHA;Boc-d-asp(otbu)-oh.dcha;BOC-D-ASP-OHDCHA;Boc-D-Asp(OtBu)-OH.DCHA;MolPort-016-580-287;C25H46N2O6;0303AB;AKOS016002241;AK-43445;ST24046500;K-5855
Boc-D-Asp(OtBu)-OH · DCHA is a protected, stereodefined aspartic acid derivative bearing a Boc-protected amino group and an OtBu-protected side-chain carboxyl, supplied as a dicyclohexylamine (DCHA) salt. This combination is widely used to control reactivity during peptide assembly by minimizing side reactions from the free amino and side-chain carboxylate functionalities, while maintaining a robust building-block profile for downstream coupling. The D configuration and the acid-stable protection pattern make it a practical choice for preparing aspartate-containing peptide segments where stereochemical fidelity and orthogonal functional-group handling are important.
1. Solid-Phase Peptide Synthesis
Boc-D-Asp(OtBu)-OH · DCHA is used by peptide synthesis groups to incorporate D-aspartate residues into peptide sequences under protected-amino-acid workflows. The Boc group on the α-amino functionality and the OtBu protection on the side-chain carboxyl help suppress unwanted side-chain participation during segment coupling and purification, supporting reliable assembly of D-Asp-containing peptides for structure-activity relationship studies and peptide stability investigations. Peptide manufacturers and academic peptide cores often select this specific protected form when they require a stereodefined D-aspartate building block that behaves consistently across automated or semi-automated synthesis campaigns.
2. D-Asp Peptide Segment Building
Boc-D-Asp(OtBu)-OH · DCHA serves as a key intermediate building block for preparing D-Asp-containing peptide segments used in chemical biology and protein-chemistry workflows. Researchers developing peptidomimetics, protease-resistant peptide analogs, or conformation-focused libraries rely on stereochemically defined amino acid inputs to control local backbone geometry and side-chain placement. The OtBu-protected side-chain carboxyl is especially relevant when the downstream peptide design requires that the aspartate side chain remain protected through initial assembly steps, enabling later deprotection or functionalization at a controlled stage of the synthesis.
3. Pharmaceutical Intermediate Development
Boc-D-Asp(OtBu)-OH · DCHA is frequently employed in medicinal chemistry and pharmaceutical intermediate development as a protected amino acid precursor for generating aspartate-derived fragments and coupling-ready intermediates. Process chemistry teams use this type of protected, salt-form building block to manage reactivity during stepwise synthesis toward peptidomimetic scaffolds and aspartate-containing heterocycles or side-chain elaboration products. The DCHA salt form can be advantageous in industrial handling and dosing consistency for protected amino acid intermediates, particularly when downstream transformations require careful control of free acid/base speciation.
4. Analytical Reference Material Preparation
Boc-D-Asp(OtBu)-OH · DCHA is also used to prepare analytical reference standards and method-development materials for characterization of protected aspartate-containing intermediates and peptides. Analytical laboratories use stereodefined, side-chain protected building blocks to generate authentic standards for chromatographic identification and to support method verification for peptide synthesis monitoring, impurity profiling, and deprotection step assessment. Because the protection pattern matches common peptide-synthesis protecting-group logic, this reagent can be incorporated into workflow-specific standard sets used in LC-based or related analytical pipelines during development and quality evaluation of peptide intermediates.
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