L-Aspartic acid dimethyl ester hydrochloride contains the aspartic acid backbone with a side-chain carboxyl group and is present as a dimethyl ester derivative, converting both the α-carboxyl group and the side-chain carboxyl group into methyl ester functionalities while retaining an amino group. The molecule is supplied as a hydrochloride salt, featuring an ammonium chloride form that alters protonation state and improves handling relative to the free amino ester, and it is specified as the L stereoisomer at the α-carbon. In synthesis and analytical workflows, this amino acid ester hydrochloride functions as a protected, esterified building block for preparing aspartate-containing peptide intermediates and for generating more complex aspartate derivatives through controlled deprotection or subsequent functional-group transformations.
CAT No: CP00452
CAS No:32213-95-9
Synonyms/Alias:32213-95-9;L-Asparticaciddimethylesterhydrochloride;H-Asp(ome)-OMeHCl;DimethylL-aspartatehydrochloride;H-Asp(OMe)-OMe.HCl;methylasparticacidhydrochloride;asparticaciddimethylesterhydrochloride;L-asparticaciddimethylesterhydro-chloride;(S)-AminosuccinicAcidDimethylEsterHydrochloride;PubChem10903;AC1Q3BVC;H-Asp(OMe)-OMeinvertedexclamationmarkcurrencyHCl;H-Asp(OMe)-OH.HCl;KSC491O1D;H-Asp(OMe)-OMeHydrochloride;456233_ALDRICH;AC1MC268;SCHEMBL1802204;CTK3J1711;MolPort-003-933-463;PNLXWGDXZOYUKB-WCCKRBBISA-N;ACT07875;ANW-27304;DimethylL-AsparaginateHydrochloride;MFCD00038878
L-Aspartic acid dimethyl ester hydrochloride is the hydrochloride salt form of L-aspartic acid dimethyl ester, featuring the L-configured stereocenter at the α-carbon and a side-chain β-carboxyl group converted to a dimethyl ester. The molecule contains two ester functionalities (α- and β-ester) that modulate polarity and reactivity relative to the free amino acid, while the amino functionality is present as a salt-associated amine that can be engaged in peptide coupling after appropriate basification and activation. The ester-protected carboxyl groups support controlled downstream transformations such as selective hydrolysis, transesterification, or conversion to acid/amide handles, enabling stepwise construction of aspartate-derived motifs. As a chiral amino acid ester intermediate, it participates in protected amino acid synthesis strategies and can be routed toward peptide building block preparation, chiral derivatization, and process chemistry intermediates requiring stereochemical fidelity.
1. Protected Peptide Building Blocks
L-Aspartic acid dimethyl ester hydrochloride supports peptide synthesis workflows where aspartate side-chain protection and controlled deprotection are required for coupling chemistry. The L-aspartate backbone provides an α-amino ester framework, while the β-carboxyl is masked as a dimethyl ester to reduce side reactions during amide bond formation. Peptide coupling compatibility can be achieved by converting the amine to an N-protected form and by using ester hydrolysis or selective activation to reveal the desired C-terminal or side-chain carboxyl functionality at the appropriate stage. Downstream, the compound can serve as a stereodefined intermediate for aspartate-containing peptide segments and aspartate-rich analogs used in peptide science and biochemical research.
2. Side-Chain Functionalization Chemistry
L-Aspartic acid dimethyl ester hydrochloride is applicable to side-chain functionalization and derivatization strategies that begin from an ester-stabilized aspartate scaffold. The β-dimethyl ester group can undergo controlled transformations to generate activated carboxylic acid derivatives, amide-linked side-chain analogs, or further functional groups used in molecular design. The stereochemical integrity of the L-configuration helps maintain consistent spatial presentation of the side-chain functionality in subsequent conjugation or scaffold elaboration. The resulting aspartate-derived intermediates can be used to build peptidomimetics, generate structure-defined chemical probes, and prepare functional molecules for chemical biology studies.
3. Process Chemistry Intermediate
L-Aspartic acid dimethyl ester hydrochloride fits process chemistry intermediate preparation where ester-protected amino acid derivatives are processed through scalable protection, activation, and deprotection sequences. The hydrochloride salt form can facilitate handling and controlled basification steps to enable downstream derivatization while maintaining the chiral center. The dimethyl ester pattern provides a chemically manageable platform for selective hydrolysis to the monoacid or conversion to activated carboxyl species for subsequent coupling in manufacturing routes. Industrially relevant downstream utility includes preparation of aspartate building blocks for fine chemical synthesis and pharmaceutical intermediate development, where predictable functional group interconversions are required.
4. Chemical Biology Probes
L-Aspartic acid dimethyl ester hydrochloride can be employed in chemical biology research to generate aspartate-based probes and labeling-ready intermediates. The amino acid ester framework allows conversion into N-protected derivatives and carboxyl-activated forms suitable for attaching to biomolecule-reactive scaffolds under controlled chemoselectivity. The β-carboxyl functionality, once transformed from the dimethyl ester into an acid or activated ester, can be used to introduce defined linkers that mimic aspartate recognition elements in biochemical systems. The stereodefined L-aspartate motif supports construction of structure-anchored probes and peptide analogs used for studying molecular recognition and protein interaction motifs.
5. Analytical Standards And Derivatization
L-Aspartic acid dimethyl ester hydrochloride serves as a chiral reference and derivatization precursor for analytical method development targeting aspartate-containing compounds. The dimethyl ester form can be used to standardize chromatographic behavior and facilitate detection workflows that distinguish stereoisomeric or functional-group-specific species. Conversion to defined acids, amides, or N-protected derivatives enables consistent comparison across sample sets in amino acid derivative profiling and peptide-related analyses. The compound's well-defined stereochemistry and functional group pattern make it suitable for preparing analytical standards and calibration materials in research-grade biochemical and synthetic chemistry contexts.
6. Peptidomimetics Construction
L-Aspartic acid dimethyl ester hydrochloride supports peptidomimetic construction by providing a stereodefined aspartate core that can be elaborated into non-natural backbones or side-chain constrained analogs. The protected ester groups allow staged functional group interconversion, including transformation into carboxyl activation states or amide-forming handles that can be incorporated into scaffold-building reactions. The L-configuration at the α-carbon helps preserve spatial arrangement important for mimicking aspartate geometry in receptor-binding studies and structure-activity relationship investigations. Downstream, the compound can be routed into aspartate-containing analog libraries and synthetic intermediates used in SAR studies and molecular design efforts.
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