Boc-L-aspartic acid is an N-Boc protected form of L-aspartic acid, featuring the aspartate side chain with a terminal carboxylic acid and a free α-amino acid backbone. The molecule contains an α-carboxyl group and an α-amino group masked as a Boc carbamate, which reduces undesired amine reactivity during synthesis while retaining the side-chain carboxyl functionality for subsequent coupling or selective derivatization. In peptide chemistry and amino acid derivative preparation, this protected amino acid is used as a stepwise building block to control chemoselectivity and to introduce an aspartate residue bearing a carboxyl side chain into protected peptide intermediates.
CAT No: CP00406
CAS No:13726-67-5
Synonyms/Alias:Boc-Asp-OH;13726-67-5;N-(tert-Butoxycarbonyl)-L-asparticacid;Boc-L-asparticacid;Boc-L-Asp-OH;N-Boc-L-asparticAcid;KAJBMCZQVSQJDE-YFKPBYRVSA-N;tert-Butoxycarbonyl-L-asparticacid;SBB065838;(S)-2-(TERT-BUTOXYCARBONYLAMINO)SUCCINICACID;(2S)-2-[(tert-butoxy)carbonylamino]butanedioicacid;N-alpha-t-BOC-L-ASPARTICACID;N-(tert-butoxycarbonyl)asparticacid;N-tert-Butyloxycarbonyl-L-asparticacid;N-Bocasparticacid;204523-15-9;PubChem12926;BOC-L-ASP;AC1Q5XNG;KSC174S5R;CHEMBL17509;SCHEMBL688341;BOC-L-ASPARTICACID-OH;408468_ALDRICH;AC1L413F
Boc-L-aspartic acid is an L-aspartate building block bearing a tert-butoxycarbonyl (Boc) group on the amino functionality and a side-chain carboxylic acid that is available for further conversion or selective protection strategies during peptide assembly. As a protected amino acid, it is commonly selected in peptide chemistry workflows where controlled handling of the acidic side chain is required to maintain coupling efficiency and minimize side reactions. Its defined stereochemistry and protected backbone make it a practical intermediate for constructing aspartate-containing peptides and peptide segments.
1. Solid-Phase Peptide Synthesis
Boc-L-aspartic acid is used by peptide synthesis groups to introduce an aspartate residue into peptide sequences while maintaining a protected amino group for iterative coupling. In solid-phase peptide synthesis workflows, the Boc-protected backbone supports reliable stepwise assembly, and the side-chain carboxyl functionality provides a handle for generating aspartate-containing motifs after appropriate side-chain management. Peptide manufacturers and academic peptide chemistry labs often choose this protected aspartate form when they need a controlled, well-defined amino acid segment for custom peptide synthesis, including sequences where the acidic side chain must be handled carefully to avoid aggregation or undesired side reactions during chain elongation.
2. Aspartate Side-Chain Functionalization
Boc-L-aspartic acid is frequently employed as a protected aspartate precursor for downstream derivatization of the side-chain carboxyl group, enabling access to aspartate variants used in peptide and materials research. Researchers preparing modified peptide segments use the free side-chain carboxyl to generate activated derivatives or to incorporate aspartate-based functionality into larger constructs, such as acidic motifs for solubility tuning or for building blocks used in chemical biology probes. This product's Boc-protected amino group helps maintain compatibility with multi-step workflows where the side chain must be selectively transformed while preserving the integrity of the amino acid backbone during intermediate handling.
3. Pharmaceutical Intermediate Development
Boc-L-aspartic acid is used in medicinal chemistry and pharmaceutical intermediate development as a stereochemically defined, protected amino acid starting material for constructing aspartate-containing fragments. Process development teams and custom synthesis providers rely on this building block to access protected aspartate units that can be further converted into coupling-ready intermediates for incorporation into peptidomimetic scaffolds or peptide-like structures. The combination of L-configuration and Boc protection supports controlled downstream transformations, which is particularly valuable when the acidic side chain needs to be carried through as a functional group while the amino functionality is managed to fit the planned synthetic sequence.
4. Peptide Library Construction
Boc-L-aspartic acid is applied in peptide library workflows where aspartate-containing diversity is required across multiple analogs, including studies that compare sequence context or side-chain modifications. Peptide engineering groups and screening-oriented chemistry teams use protected aspartate building blocks to standardize the incorporation of the aspartate residue across parallel syntheses, improving reproducibility of coupling and purification outcomes. The protected amino functionality and defined stereochemistry make it a practical reagent for generating aspartate-bearing peptide sets, including libraries designed for structure-activity relationship exploration in peptide-based research programs.
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