Boc-D-Asp(OcHex)-OH is a protected, D-configured amino acid derivative based on aspartic acid bearing an N-terminal Boc (tert-butoxycarbonyl) protecting group and a side-chain esterified carboxyl functionality as OcHex (hexyl ester). The molecule contains both an amino group masked by the Boc carbamate and a free carboxylic acid at the α-position, while the side-chain carboxyl is converted to a hexyl ester that modulates polarity and suppresses side-chain carboxyl reactivity during coupling steps. In peptide synthesis workflows, this protected analogue functions as a stepwise building block that supports controlled chemoselectivity at the α-carboxyl/amine coupling site while the Boc and OcHex groups help manage protection of the additional acidic functionality.
CAT No: CP26200
CAS No:112898-18-7
Synonyms/Alias:112898-18-7;boc-d-asp(ochex)-oh;Boc-D-Asp(OcHx)-OH;(R)-2-((tert-Butoxycarbonyl)amino)-4-(cyclohexyloxy)-4-oxobutanoicacid;Boc-D-asparticacid4-cyslohexylester;15073_ALDRICH;15073_FLUKA;MolPort-003-926-629;ZINC2528219;8974AC;AKOS015903655;CB-1660;AJ-38255;AK154818;KB-309761;FT-0679696;K-0977;N-Alpha-t-Boc-D-asparticbeta-cyclohexylester;I14-17891;(2R)-2-[(tert-butoxycarbonyl)amino]-4-(cyclohexyloxy)-4-oxobutanoicacid
Boc-D-Asp(OcHex)-OH is a D-configured, protected aspartic acid derivative designed for peptide and intermediate synthesis. The amino group is protected as a Boc carbamate, while the side-chain carboxylic acid is masked as an OcHex ester, providing controlled reactivity during sequence assembly. This protected stereochemical and functional-group pattern makes it a practical building block for incorporating D-aspartate residues into peptides where side-chain carboxyl handling is required.
1. D-Asp Peptide Building Blocks
Boc-D-Asp(OcHex)-OH is used by peptide synthesis groups to assemble peptides containing D-aspartate residues, including stereochemically defined analogs for structure-activity relationship studies. The Boc-protected amino functionality supports standard stepwise peptide coupling workflows, while the OcHex ester on the side-chain carboxyl helps keep the Asp side chain from interfering during chain elongation. Researchers commonly select this type of protected D-Asp building block when they need reliable chemoselectivity and predictable downstream deprotection to access the free side-chain carboxyl for subsequent modifications or final peptide characterization.
2. Solid-Phase Peptide Synthesis Segments
Boc-D-Asp(OcHex)-OH is frequently incorporated into SPPS segment synthesis where protected amino acid building blocks are assembled into peptide sequences for later purification and analytical confirmation. The orthogonal protection strategy—Boc on the α-amino group and OcHex on the side-chain carboxyl—supports efficient assembly of Asp-containing segments while reducing side reactions associated with unprotected carboxylic acids. Custom peptide manufacturers and academic peptide chemistry labs use this reagent to prepare D-Asp-containing peptides used in binding studies, protease selectivity experiments, and conformational investigations, where maintaining the D-configuration at the residue is essential to the experimental design.
3. Asp Side-Chain Functionalization Precursors
Boc-D-Asp(OcHex)-OH serves as a protected precursor for workflows that require controlled access to the Asp side-chain carboxyl group after peptide assembly. After deprotection of the OcHex ester in the appropriate stage of the synthesis plan, the resulting free side-chain carboxyl can be used for subsequent derivatization steps such as coupling to linkers, generating activated esters/amides, or enabling further chemical modifications on peptide scaffolds. Medicinal chemistry and chemical biology teams often rely on this approach to prepare stereochemically defined peptide conjugates and intermediate fragments where the timing of side-chain unmasking is critical for minimizing byproducts and preserving sequence integrity.
4. Pharmaceutical Intermediate Development
Boc-D-Asp(OcHex)-OH is also used in the development of stereochemically defined pharmaceutical intermediates and peptidomimetic building blocks that incorporate D-Asp motifs. Process chemistry and medicinal chemistry groups value the protected, well-defined functional-group pattern because it supports downstream transformations while limiting uncontrolled reactivity from both the α-amino and side-chain carboxyl functionalities. This reagent is commonly selected when the synthesis route requires a protected D-aspartate unit that can be carried through intermediate steps and then converted into a more reactive or coupling-ready form at a controlled stage of the overall manufacturing or library-building workflow.
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