L-Aspartic acid α-benzyl ester is an amino acid ester derived from the proteinogenic amino acid aspartic acid, featuring a side-chain carboxylic acid and an α-carboxyl group converted to a benzyl ester while retaining the amino acid backbone. The molecule contains a free primary amino group and a carboxylic acid side chain, with stereochemistry indicated as L at the α-carbon, and the benzyl ester provides protection of the α-carboxyl functionality against undesired reactions during chemical transformations. In peptide and amino acid derivative synthesis, this ester form is used as a protected, stepwise intermediate that supports controlled manipulation of the remaining functional groups and can serve as a precursor for further esterification, amidation, or conversion into peptide-coupling-ready derivatives.
CAT No: CP00447
CAS No:7362-93-8
Synonyms/Alias:H-Asp-OBzl;7362-93-8;(S)-3-Amino-4-(benzyloxy)-4-oxobutanoicacid;L-AsparticAcid1-BenzylEster;L-Asparticacidbenzylester;1-BenzylL-Aspartate;H-Asp-OBzl.HCl;H-ASPObzl;AC1ODWBZ;PubChem14915;SCHEMBL169622;AC1Q4U76;L-Asparticacida-benzylester;CTK3J1667;L-Asparticacid|A-benzylester;MolPort-003-983-017;NJSRYBIBUXBNSW-VIFPVBQESA-N;ACT10910;ZINC1709637;KM1560;SBB064137;AKOS015889981;AKOS015924122;AM81595;RTR-030856
L-Aspartic acid α-benzyl ester is an L-amino acid ester derivative featuring the aspartate side-chain carboxylic acid functionality protected as a benzyl ester while the α-amino group remains available for peptide coupling or further protection strategies depending on the synthetic sequence. The molecule contains a stereogenic center at the α-carbon, enabling stereochemically defined incorporation into peptide building blocks and chiral intermediate routes. The benzyl ester introduces an acid-labile and hydrogenolysis-compatible protecting handle for the side-chain carboxyl group, while the α-ester form supports controlled downstream transformations such as selective deprotection, selective amidation, or activation for chain extension. The presence of a protected carboxyl group and the amino acid backbone makes the compound suitable for derivatization workflows that require orthogonal protection and predictable reactivity under standard peptide coupling conditions.
1. Peptide Synthesis
L-Aspartic acid α-benzyl ester is used in peptide building block preparation where the L-aspartate stereocenter and the side-chain benzyl ester enable controlled formation of Asp-containing sequences. The amino acid ester framework can be converted into coupling-ready derivatives after appropriate amino protection, while the benzyl-protected side-chain carboxyl group can be preserved during chain assembly to prevent undesired crosslinking or side reactions. Hydrogenolysis or other benzyl-cleaving strategies can later unmask the side-chain carboxyl for subsequent amide formation, salt formation, or further functionalization. The resulting Asp-containing intermediates support stepwise peptide construction and the synthesis of peptides with defined side-chain chemistry for biochemical research and materials-oriented peptide engineering.
2. Side-Chain Functionalization
L-Aspartic acid α-benzyl ester serves as a chiral precursor for side-chain functionalization workflows that require orthogonal control over the aspartate carboxyl group. The benzyl ester protects the side-chain carboxyl during initial manipulations, allowing selective transformations at the α-amino functionality or at the ester/activated carboxyl handles introduced later in the sequence. Side-chain deprotection can generate a free carboxylate suitable for conversion to amides, esters, or activated derivatives used in coupling chemistry and molecular scaffold diversification. The L-configuration and protected carboxyl reactivity pattern enable downstream synthesis of aspartate-based analogs used in chemical biology tool development, peptidomimetic design, and structure-directed derivatization.
3. Chiral Building Block Synthesis
L-Aspartic acid α-benzyl ester is applicable in chiral synthesis planning as an aspartate-derived intermediate that carries a defined L-stereochemistry and a removable benzyl ester protecting group. The stereogenic α-carbon provides stereochemical fidelity for incorporation into peptide-like structures, while the benzyl ester offers a practical protecting-group handle to manage functional group compatibility across multiple synthetic steps. The protected carboxyl can be selectively unmasked to generate a stereodefined carboxylate for further coupling or for conversion into activated electrophiles used in fine chemical synthesis. The compound's structure supports stereocontrolled preparation of chiral amino acid derivatives and intermediate streams used in research-grade and industrial-scale manufacturing of amino acid-based specialty chemicals.
4. Chemical Biology Probes
L-Aspartic acid α-benzyl ester can be employed to construct chemical biology probes and labeling reagents that depend on aspartate side-chain carboxyl chemistry. The benzyl-protected side-chain carboxyl enables staged introduction of reactive handles, such as carboxylate activation for amide bond formation or transformation into functional groups compatible with conjugation strategies. The L-aspartate backbone can be integrated into peptide tags, enzyme-interaction motifs, or biomolecule-binding scaffolds where stereochemistry influences molecular recognition. The ability to unmask the side-chain carboxyl from a protected ester supports downstream conjugation to amines, hydrazides, or other nucleophiles, enabling generation of defined aspartate-containing probes for biochemical investigation and applied molecular design.
5. Pharmaceutical Intermediate Preparation
L-Aspartic acid α-benzyl ester is suitable for pharmaceutical intermediate preparation where amino acid ester and protected side-chain carboxyl functionality support controlled synthesis of peptidic and peptidomimetic fragments. The benzyl ester protecting group can be maintained through intermediate formation steps and later removed to reveal a carboxylic acid for activation, salt formation, or conversion to amide-linked motifs common in medicinal chemistry. The L-stereochemistry at the α-carbon supports stereochemically defined fragment assembly for SAR-oriented synthesis and for generating libraries of aspartate-containing analogs. The compound's functional group pattern aligns with process chemistry intermediate design, enabling manufacturable routes to protected amino acid derivatives used in downstream fine chemical synthesis and specialty ingredient production where defined stereochemistry and orthogonal protection are required.
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