L- Aspartic acid is a naturally occurring, proteinogenic amino acid featuring an aliphatic side chain terminated by a carboxylic acid, classifying it as an acidic amino acid. It contains a free α-amino group and a free α-carboxyl group on the backbone, with the side-chain carboxyl group providing additional acid functionality that can participate in hydrogen bonding and ionic interactions depending on pH, and the name indicates the L stereochemical form. As a free amino acid, it is used as a building block for peptide and protein synthesis in solution-phase or solid-phase workflows and as a substrate component in biochemical and analytical studies where an acidic amino acid residue is required.
CAT No: CP00403
CAS No:56-84-8
Synonyms/Alias:Z-Glu(OBzl)-OH;5680-86-4;Cbz-Glu(Obzl)-OH;(S)-5-(Benzyloxy)-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoicacid;(S)-2-Benzyloxycarbonylamino-PentanedioicAcid5-BenzylEster;AC1MIOMC;PubChem14964;AC1Q71CW;5-BenzylN-Cbz-L-glutamate;SCHEMBL7373019;CTK1H3654;MolPort-001-792-719;ZINC1678300;5-BenzylN-Carbobenzoxy-L-glutamate;ANW-43281;CZ-036;MFCD00065697;AKOS015924087;CS11155;DS-1091;MCULE-2794987345;N-Cbz-L-glutamicAcid5-BenzylEster;RTR-019900;VA50254;N-Cbz-L-glutamicacidgamma-benzylester
L-Aspartic acid is a proteinogenic amino acid with an L-stereogenic center at the alpha carbon and a side chain containing a carboxylic acid functionality, giving it two carboxyl groups and one primary amino group. The zwitterionic character in aqueous media and the ability to form salts and internal hydrogen-bonding networks influence solubility, buffering behavior, and compatibility with peptide coupling conditions. The side-chain carboxyl group participates in amide bond formation and can be selectively masked through protecting-group strategies to control mono- versus di-functional derivatization. As a chiral, bifunctional amino acid, L-aspartic acid functions as a chemically defined intermediate for peptide building block preparation, amino acid derivatization, and downstream synthesis of aspartate-containing motifs.
1. Peptide Synthesis
L-Aspartic acid supports peptide coupling chemistry through its alpha-amino and alpha-carboxyl groups, enabling incorporation as an aspartate residue in linear peptides and protected peptide fragments. The side-chain carboxylic acid can be protected as an orthogonal group during N- and C-terminal protection planning, allowing selective formation of the desired amide bonds without cross-reactivity. The L-configuration at the alpha carbon preserves stereochemical integrity during standard peptide assembly and subsequent deprotection steps. L-Aspartic acid-derived protected forms are therefore used to prepare aspartate-containing peptide building blocks and to construct peptide sequences where side-chain carboxyl reactivity must be controlled for sequence fidelity and purification.
2. Side-Chain Functionalization
L-Aspartic acid enables side-chain carboxyl functionalization routes that translate the aspartate motif into chemically diverse derivatives for synthetic organic chemistry and chemical biology workflows. The side-chain carboxylic acid can be converted into activated esters, amides, or other carboxyl-derived linkers, while the alpha-amino group can be protected to prevent undesired N-acylation during functional group installation. Orthogonal protection strategies allow sequential modification, including selective derivatization of the side-chain carboxyl while maintaining a protected amino handle for later coupling. Downstream products include aspartate-based conjugation handles, carboxyl-anchored linkers, and intermediate scaffolds used to generate functional molecules that retain the stereochemical definition of the L-aspartate core.
3. Bioconjugation Chemistry
L-Aspartic acid can be applied in bioconjugation and biomolecule modification contexts where carboxyl-directed coupling provides a controlled attachment point for probes, linkers, or affinity tags. The presence of both an amino functionality and a side-chain carboxyl group supports linker design that can be tuned by selective protection and activation to favor chemoselective attachment. L-aspartic acid derivatives can be used to build peptide-like linkers that undergo amide bond formation with activated carboxylates or activated esters on biomolecular partners. Resulting conjugates are useful in biochemical research intermediate preparation, including reagent construction for labeling strategies and the generation of aspartate-bearing molecular tools for studying macromolecular interactions.
4. Protein Engineering
L-Aspartic acid serves as a chiral building block for protein engineering and protein chemistry applications that require defined aspartate-containing segments or aspartate analogs. The side-chain carboxyl group is a key structural element for mimicking acidic residues in engineered peptides and for designing local charge environments that influence folding or binding interfaces. Protected L-aspartic acid derivatives can be incorporated into peptide constructs used as substrates, standards, or reference materials in protein-related studies where stereochemistry and side-chain functionality must match the intended residue identity. L-aspartic acid-based intermediates thus support the synthesis of engineered peptide regions and aspartate-modified biomolecular reagents used in applied protein science.
5. Pharmaceutical Manufacturing
L-Aspartic acid is suitable for pharmaceutical intermediate preparation in manufacturing-oriented workflows that require chiral amino acid feedstocks for downstream synthesis of peptide-derived actives, intermediates, or process-compatible building blocks. The bifunctional nature of the amino acid, with an alpha-amino group and two carboxyl groups, enables controlled conversion into protected amino acid derivatives that can be sequenced into peptide fragments under process chemistry conditions. Protecting-group selection and orthogonality considerations are central for managing selective coupling at the intended functional site while maintaining the L stereocenter through manufacturing steps. L-Aspartic acid therefore functions as a practical chiral intermediate for fine chemical synthesis routes that generate aspartate-containing intermediates used in industrial-scale peptide and amino acid derivative production.
6. Analytical Research Standards
L-Aspartic acid can be employed in analytical research as a chemically defined reference material for amino acid profiling, method development, and calibration in chromatographic and spectrometric workflows. The distinct functional group pattern, including the side-chain carboxyl group, supports reproducible derivatization behavior and enables consistent interpretation of aspartate-containing sample mixtures. L-Aspartic acid-derived standards and derivatized forms can be used to validate analytical selectivity and to support identification of aspartate residues in peptide hydrolysates or amino acid derivative libraries. The chiral, bifunctional structure makes L-aspartic acid a reliable anchor compound for analytical method verification tied to amino acid derivatization and peptide chemistry downstream analysis.
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