D-Alanine tert.butyl ester hydrochloride is a D-configured amino acid ester in which the alanine amino acid backbone is converted to a tert-butyl ester at the carboxyl terminus. The molecule contains a free amino functionality on the alanine side and a tert-butyl ester group, with hydrochloride association forming an amino hydrochloride salt that modulates solubility and basicity. As an amino acid ester hydrochloride, it is commonly used as a protected or masked carboxyl building block for peptide and amide bond formation in solution-phase or stepwise synthetic routes, and it can serve as a precursor for preparing alanine-containing derivatives and analytical standards.
CAT No: CP00133
D-Alanine tert.butyl ester hydrochloride is a D-configured amino acid ester salt in which the amino group is present as a hydrochloride while the carboxyl functionality is masked as a tert-butyl ester. The molecule therefore combines a stereochemically defined chiral center at the alpha carbon with an ester-protected carboxyl group that can be selectively deprotected under acid conditions, while the tert-butyl moiety provides robust protection during peptide coupling and intermediate handling. The hydrochloride form improves handling of the amine as a defined salt and can influence solubility and reactivity in coupling media. As a chiral amino acid ester intermediate, it participates in amino acid derivatization workflows that require controlled protection states and predictable downstream conversion to D-alanine-containing building blocks.
1. Peptide Coupling Building Block
D-Alanine tert.butyl ester hydrochloride is suitable for peptide synthesis workflows where a D-alanine residue must be incorporated under controlled N- and C-protection logic. The tert-butyl ester masks the carboxyl group to reduce side reactions during amide bond formation, while the D-configuration supports stereospecific incorporation into peptide chains and peptidomimetic scaffolds. Salt formation at the amine can facilitate consistent reactivity during coupling sequence design, and subsequent ester deprotection can regenerate the free carboxyl for further elongation or for conversion to activated peptide fragments. Downstream use commonly includes preparation of D-alanine-containing peptide building blocks and analogs used to probe stereochemical effects in peptide chemistry and biochemical research.
2. Protected Amino Acid Synthesis
D-Alanine tert.butyl ester hydrochloride functions as a practical chiral amino acid ester precursor for producing protected D-alanine derivatives used in synthetic organic chemistry. The tert-butyl ester provides a protection strategy compatible with many coupling conditions, and its acid-labile character enables controlled deprotection to access the corresponding D-alanine carboxylic acid when needed for activation or further derivatization. The hydrochloride-associated amine can be managed as a defined intermediate state, supporting stepwise protection and deprotection planning for N-functionalization. Resulting derivatives can include N-protected D-alanine building blocks, activated carboxylates, and other intermediates that feed into peptide construction, SAR studies, and stereochemically defined fragment assembly.
3. Chiral Intermediate For SAR Studies
D-Alanine tert.butyl ester hydrochloride can be applied in structure-activity relationship studies requiring stereochemically defined substitutions at the amino acid position. The D-alanine stereocenter enables systematic comparison of stereoisomer effects in peptidomimetics, constrained amino acid analogs, and amino acid-derived fragments used in medicinal chemistry. The ester-protected carboxyl group supports controlled functional group interconversions, enabling conversion into carboxylic acid forms for coupling, cyclization, or incorporation into larger scaffolds. Downstream synthetic utility includes generation of D-alanine-containing intermediates for library synthesis and molecular design campaigns where stereochemical fidelity is critical.
4. Process Chemistry Intermediate
D-Alanine tert.butyl ester hydrochloride is relevant to process chemistry intermediate preparation for fine chemical and pharmaceutical intermediate manufacturing routes that require stable, isolable amino acid derivatives. The tert-butyl ester protection strategy supports handling stability during multi-step sequences, while its acid-labile deprotection behavior can be aligned with downstream conversion to carboxylic acid functionality for activation steps. The hydrochloride salt form can assist in reproducible material handling and may support consistent feedstock properties in industrial batch processing. Resulting material streams can feed into amino acid derivative production, peptide fragment preparation, and other industrially scaled syntheses that rely on chiral amino acid ester intermediates.
5. Analytical Standard Development
D-Alanine tert.butyl ester hydrochloride can serve as an analytical reference material for method development and stereochemical verification in amino acid and peptide analysis. The defined D-configuration and ester form provide a chemically characterized target for chromatographic separation, mass spectrometric identification, and impurity profiling of amino acid ester intermediates. The hydrochloride and tert-butyl ester functionalities create recognizable ionization and fragmentation patterns that can be used to benchmark analytical workflows during protected amino acid synthesis and peptide building block preparation. Downstream relevance includes supporting quality control for intermediate identity, monitoring deprotection progress, and validating analytical methods used in peptide chemistry supply chains.
6. Amino Acid Derivatization And Side-Chain Functionalization
D-Alanine tert.butyl ester hydrochloride is suitable for derivatization routes that modify amino acid functionality while preserving the D-stereocenter. The ester-protected carboxyl group can be maintained during selective transformations on the amine and can be unmasked when required for subsequent coupling or functional group installation. The hydrochloride-associated amine state can be leveraged to manage reactivity during formation of N-substituted derivatives, including N-protected or N-functionalized intermediates used to build amide, urea, or other nitrogen-containing motifs. Resulting derivatives can be incorporated into peptidomimetic construction, biochemical probe synthesis, and downstream synthetic schemes that require controlled amino acid functional group presentation.
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