Boc-L-aspartic acid α-benzyl ester is a protected L-aspartic acid derivative in which the α-amino group is masked as a Boc carbamate and the α-carboxyl group is esterified as a benzyl ester, yielding an aspartate side chain with a free β-carboxylic acid. The molecule contains both a Boc-protected amine and a β-carboxyl functional group that can participate in acid-base behavior and coupling chemistry, while the benzyl ester provides a removable carboxyl protecting group for stepwise synthesis. In peptide synthesis workflows, this compound is employed as a protected amino acid building block to control chemoselectivity during amide bond formation and to enable selective handling of the α-carboxyl functionality while retaining a side-chain carboxyl for further derivatization or incorporation into aspartyl-containing peptide structures.
CAT No: CP00408
CAS No:30925-18-9
Synonyms/Alias:Boc-Asp-OBzl;30925-18-9;Boc-L-asparticacid1-benzylester;SBB066995;N-(tert-Butoxycarbonyl)-L-asparticAcid1-BenzylEster;1-BenzylN-Boc-L-aspartate;(3S)-4-(benzyloxy)-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoicacid;1-BenzylN-(tert-Butoxycarbonyl)-L-aspartate;Commericial;(3S)-3-[(tert-butoxy)carbonylamino]-3-[benzyloxycarbonyl]propanoicacid;PubChem12927;AC1Q1MRP;15066_ALDRICH;Boc-asparticacidbenzylester;SCHEMBL1093029;15066_FLUKA;LDRWTKQWSXGSTM-LBPRGKRZSA-N;MolPort-003-926-625;ACT05195;Boc-L-asparticacida-benzylester;ZINC2539200;ANW-59149;CB-208;MFCD00065563;AKOS015924100
Boc-L-aspartic acid α-benzyl ester is a protected L-aspartic acid building block designed for peptide and peptidomimetic synthesis, featuring a Boc-protected amino group and an α-benzyl ester that masks the carboxyl functionality for controlled coupling chemistry. The aspartate side chain remains protected as the corresponding ester form, enabling downstream deprotection and segment assembly strategies that are common in protected amino acid workflows. This reagent is widely used by custom peptide synthesis groups and medicinal chemistry teams preparing aspartate-containing sequences where orthogonal deprotection and reliable condensation are required.
1. Solid-Phase Peptide Synthesis
Boc-L-aspartic acid α-benzyl ester is used in solid-phase peptide synthesis workflows to incorporate an aspartate residue with controlled functional group masking during chain assembly. Peptide synthesis groups select this protected aspartate derivative when they need a Boc-protected amino functionality compatible with their stepwise coupling and deprotection schedule, while the α-benzyl ester helps prevent premature side reactions of carboxyl groups during peptide elongation. This format is particularly useful for preparing aspartate-containing peptide segments used in structure-activity relationship studies and peptide library construction, where consistent building block performance and predictable handling are important.
2. Aspartate Segment Coupling
Boc-L-aspartic acid α-benzyl ester is commonly employed as a segment coupling component in solution-phase peptide synthesis and in the preparation of protected peptide intermediates. Medicinal chemistry and process development teams use this building block to assemble aspartate-containing fragments with minimized side reactions from carboxyl groups, supporting cleaner condensation steps and more robust intermediate purification. The Boc protection pattern and benzyl ester masking align with workflows that rely on sequential deprotection to reveal reactive termini at defined stages, enabling efficient generation of defined peptide architectures for downstream biological evaluation and analytical characterization.
3. Pharmaceutical Intermediate Development
Boc-L-aspartic acid α-benzyl ester serves as a practical protected amino acid intermediate for manufacturing and development of aspartate-derived scaffolds beyond final peptide products. Pharmaceutical intermediate teams use this reagent to access protected aspartate motifs for incorporation into peptidomimetic structures, linker units, and other medicinal chemistry intermediates where controlled protection of amino and carboxyl functionalities is required during multi-step synthesis. The protected, esterified form supports handling under standard organic synthesis conditions and helps maintain functional group integrity while the overall synthetic route builds complexity through selective transformations.
4. Peptide Library and SAR Studies
Boc-L-aspartic acid α-benzyl ester is frequently selected by laboratories building peptide libraries and conducting structure-activity relationship studies that require systematic variation around an aspartate position. Custom peptide synthesis providers and academic medicinal chemistry groups use this protected aspartate building block to generate aspartate-containing analogs with consistent stereochemical identity and defined functional group protection, supporting parallel synthesis of multiple candidates. The reagent's protected form helps streamline assembly of analog series where downstream deprotection and final functional group unveiling must be coordinated across many analogs for comparative analytical and characterization workflows.
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