D-Alanine methyl ester hydrochloride is the D-enantiomer of alanine converted to the corresponding methyl ester and present as a hydrochloride salt, making it an amino acid ester derivative rather than a free amino acid. The molecule contains an esterified carboxyl group (-COOCH3) and an amino group that is protonated as a chloride salt, with stereochemistry specified as D at the α-carbon and a simple methyl side chain characteristic of alanine. In synthesis and analytical workflows, it functions as a protected/derivatized alanine building block for preparing alanine-containing peptides or peptide-related intermediates and as a substrate-like reference for method development where esterified, salt-form amino acid derivatives are required.
CAT No: CP00130
CAS No:14316-06-4
Synonyms/Alias:14316-06-4;D-Alaninemethylesterhydrochloride;MethylD-alaninatehydrochloride;H-D-Ala-OMe.HCl;(R)-methyl2-aminopropanoatehydrochloride;Methyl(2R)-2-aminopropanoatehydrochloride;H-D-Ala-OMe?HCl;PubChem10885;MethylD-alaninateHCl;D-Alaninemethylester,HCl;KSC491O5D;SCHEMBL104802;414549_ALDRICH;CTK3J1751;BIA0107;IYUKFAFDFHZKPI-AENDTGMFSA-N;MolPort-001-762-458;ACT07214;STR06149;EINECS238-258-3;ANW-20748;CA-319;MFCD00066141;AKOS015845998;(D)-alaninemethylesterhydrochloride
D-Alanine methyl ester hydrochloride is the hydrochloride salt of the D-enantiomer of alanine in methyl ester form, featuring a chiral α-carbon that defines stereochemical identity and a methyl ester that masks the carboxylic acid functionality for controlled reactivity. The salt form provides an ammonium chloride environment, which can improve handling and solubility while maintaining a protected-like profile for amine participation during coupling steps. The combination of an ester carbonyl and a stereogenic center makes the compound a practical chiral amino acid ester intermediate for downstream conversion into amides, peptides, and other D-alanine-containing motifs. Reactivity is dominated by ester chemistry, including aminolysis and transesterification, while the D-configuration supports stereospecific incorporation into peptide building blocks and stereochemically defined analogs.
1. Peptide Synthesis
D-Alanine methyl ester hydrochloride is used in peptide coupling workflows where a D-alanine unit must be introduced with defined stereochemistry. The methyl ester and ammonium chloride arrangement facilitate controlled transformation into an activated carboxyl equivalent for amide bond formation, enabling sequential construction of peptide chains or peptide fragments. Ester-to-amide conversion supports compatibility with standard peptide chemistry strategies, including stepwise assembly and incorporation into protected amino acid sequences after appropriate functional group interconversions. D-configuration retention supports stereochemically defined D-alanine incorporation for peptide analog construction and structure-controlled peptide synthesis.
2. Chiral Building Blocks
D-Alanine methyl ester hydrochloride serves as a chiral amino acid ester intermediate for stereoselective synthesis of D-configured compounds in synthetic organic chemistry. The α-stereocenter and ester functionality enable downstream derivatization into chiral amides, chiral ligands, or protected D-alanine derivatives used as building blocks in asymmetric or stereochemical studies. Hydrochloride salt formation can be leveraged to manage amine reactivity during ester transformations, supporting controlled conversion to carboxyl-activated forms or N-substituted products. The resulting D-alanine-based intermediates can then be carried into further chiral scaffold elaboration and stereochemical mapping of synthetic routes.
3. Amino Acid Derivatization
D-Alanine methyl ester hydrochloride is suitable for amino acid derivatization programs that require conversion of the ester into functional groups while preserving the D-configuration. The methyl ester can undergo aminolysis to yield D-alanine amides, be hydrolyzed to the corresponding D-alanine carboxylic acid, or be redirected through transesterification to install alternative ester or prodrug-like motifs. The amine functionality, present as a hydrochloride salt, can be selectively transformed into N-protected or N-functionalized derivatives depending on the chosen protection-group strategy for subsequent steps. Downstream products include D-alanine-containing intermediates for medicinal chemistry fragment elaboration, peptide-like scaffolds, and stereochemically defined biochemical research reagents.
4. Chemical Biology Probes
D-Alanine methyl ester hydrochloride can be applied in chemical biology research where D-amino acid incorporation is used to modulate peptide stability, protease resistance, or recognition patterns in biomolecular assays. The D-alanine ester form supports preparation of D-alanine-containing peptide segments that can be integrated into larger constructs after conversion to coupling-ready carboxyl or amide functionalities. Stereochemical control provided by the D-enantiomer helps maintain defined stereochemical features that are often critical for binding studies, labeling strategies, and structure-activity relationship work involving amino acid stereochemistry. The compound can therefore serve as a precursor for constructing stereodefined D-alanine motifs used in assay development and biochemical probe synthesis.
5. Pharmaceutical Intermediate Preparation
D-Alanine methyl ester hydrochloride is used as a process-relevant chiral intermediate for manufacturing routes that require D-alanine-derived fragments and controlled functional group interconversion. The ester provides a handle for iterative transformation into amide or acid forms that can feed into active pharmaceutical ingredient (API) synthesis, peptide-like intermediates, or stereochemically defined side-chain components. Hydrochloride salt handling supports practical upstream processing by maintaining the amine in a defined ionic state prior to coupling or protection steps. Downstream conversion to D-alanine acid, N-protected D-alanine derivatives, or D-alanine-containing intermediates supports fine chemical synthesis and industrial intermediate preparation where stereochemical integrity is required.
6. Analytical Standards
D-Alanine methyl ester hydrochloride is applicable for analytical research and method development that require stereochemically defined reference material. The compound's defined D-configuration and ester functionality make it suitable for preparing calibration standards or internal standards for chiral analysis, amino acid profiling, or monitoring of derivatization workflows. Ester and hydrochloride salt characteristics can support consistent chromatographic behavior when used to evaluate conversion between amino acid ester and acid forms. Stereochemically resolved D-alanine-containing standards can be employed to verify stereochemical outcomes in protected amino acid synthesis and peptide building block preparation.
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