Boc-L-aspartic acid β-benzyl ester is a protected, esterified amino acid derivative in which L-aspartic acid bears an N-Boc (tert-butoxycarbonyl) carbamate on the amino group and a β-benzyl ester on the side-chain carboxylate, yielding a molecule with both an amino-acid backbone and a protected side-chain functionality. The structure contains a free carboxylic acid at the α-position, while the side-chain carboxyl is masked as a benzyl ester and the α-amino functionality is protected as the Boc carbamate, providing chemoselectivity by reducing undesired acylation or side reactions during peptide coupling steps. This compound is used as a building block in peptide synthesis and related amino-acid derivative preparation, where the orthogonal protection pattern supports stepwise assembly and later deprotection to regenerate the aspartate side-chain carboxyl group for further functionalization or incorporation into larger peptide frameworks.
CAT No: CP00412
CAS No:7536-58-5
Synonyms/Alias:Boc-Asp(OBzl)-OH;7536-58-5;Boc-L-asparticacid4-benzylester;(S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoicacid;4-BenzylN-Boc-L-aspartate;SOHLZANWVLCPHK-LBPRGKRZSA-N;Boc-L-Asparticacid-4-benzylester;N-(tert-Butoxycarbonyl)-L-asparticacid4-benzylester;ST039913;N-alpha-t-BOC-L-aspartic-beta-benzylester;(2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoicacid;4-BenzylN-(tert-Butoxycarbonyl)-L-aspartate;AC1LUICW;PubChem12096;N-tert-Butoxycarbonyl-L-asparticacid4-benzylester;SCHEMBL84710;Asparticacid,N-carboxy-,4-benzylN-tert-butylester,L-;KSC496E7H;MLS000686264;15386_ALDRICH;SCHEMBL344669;440655_ALDRICH;CHEMBL1299590;15386_FLUKA;CTK3J6273
Boc-L-aspartic acid β-benzyl ester is an L-aspartate derivative featuring a Boc-protected alpha-amino group and a β-benzyl ester that masks the side-chain carboxyl functionality while maintaining the aspartate stereochemical configuration. This protected format is widely used to control chemoselectivity during peptide assembly, enabling selective activation and coupling at the desired position while the side-chain remains protected as a benzyl ester. As a result, it serves as a practical building block for constructing aspartate-containing peptide sequences and for preparing aspartate-based synthetic intermediates where orthogonal deprotection is required.
1. Solid-Phase Peptide Synthesis
Boc-L-aspartic acid β-benzyl ester is used by peptide synthesis groups to introduce aspartate residues into peptide chains with controlled side-chain reactivity. The Boc group on the alpha-amino functionality supports standard protected-amino-acid workflows, while the β-benzyl ester effectively suppresses side-chain carboxyl participation during coupling steps. This makes the reagent particularly useful for assembling aspartate-containing peptides on solid support when downstream steps require side-chain deprotection and subsequent functional manipulation without premature side reactions.
2. Aspartate Side-Chain Functionalization
Boc-L-aspartic acid β-benzyl ester is commonly selected for workflows that require later conversion of the aspartate side chain into a defined functional motif. By carrying the β-carboxyl as a benzyl ester, the building block allows peptide or intermediate formation under conditions that would otherwise risk side-chain activation or undesired branching. After peptide assembly or intermediate elaboration, benzyl ester removal provides access to the free β-carboxyl for subsequent derivatization, enabling preparation of aspartate-modified peptide derivatives used in chemical biology studies and structure-activity relationship development.
3. Peptide Segment Building Block
Boc-L-aspartic acid β-benzyl ester is also used in segment condensation and custom peptide manufacturing contexts where protected aspartate units must be handled with reliable chemoselectivity. The combination of Boc protection at the alpha-amino position and β-benzyl ester protection at the side chain supports the preparation of defined peptide fragments that can be coupled to other segments while minimizing competing reactivity. This approach is particularly valuable when building longer sequences that include multiple acidic residues or when the synthetic plan depends on staged deprotection to maintain sequence integrity and functional group compatibility.
4. Pharmaceutical Intermediate Development
Boc-L-aspartic acid β-benzyl ester serves as a protected aspartate intermediate for medicinal chemistry and specialty chemical development programs that require a stereochemically defined, side-chain-protected acid building block. The masked β-carboxyl group helps control reactivity during the construction of aspartate-derived scaffolds, while the Boc-protected amino group supports downstream transformations that depend on selective unmasking. In industrial and development settings, this reagent is therefore used to prepare aspartate-containing intermediates that feed into peptidomimetic or amino-acid-derived synthetic routes where orthogonal deprotection and controlled functional group exposure are essential.
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