Bzl-D-Ala-OMe*HCl

Bzl-D-Ala-OMe*HCl is a D-alanine methyl ester hydrochloride bearing a benzyl (Bzl) protecting group on the amino functionality, yielding a chiral amino acid ester with a defined stereocenter at the alpha carbon. The structure combines an N-protected amino group with a methyl ester at the carboxyl terminus, while the hydrochloride salt form improves handling and can influence coupling conditions by modulating amine protonation. The benzyl-protected amine supports peptide coupling chemistry after appropriate activation, and the ester functionality enables controlled downstream transformations such as transesterification, hydrolysis to the corresponding acid, or conversion into activated carboxyl derivatives. The D-configuration is preserved through these manipulations, making the compound a stereochemically defined intermediate for peptide building block preparation and chiral synthetic routes.

1. Peptide Synthesis

Bzl-D-Ala-OMe*HCl supports peptide building block preparation for solid-phase or solution-phase peptide synthesis workflows where a D-alanine residue is required. The benzyl-protected amine and methyl ester provide orthogonal functional-group handling: the N-protection can be removed under hydrogenolysis-compatible conditions to reveal the free amine for subsequent coupling, while the ester can be transformed into a carboxyl-activated species for amide bond formation. The hydrochloride salt form can facilitate consistent reagent handling and may improve reproducibility during protection-state transitions that precede coupling steps. Incorporation of the D-Ala stereocenter into peptide chains enables stereodefined analog construction and downstream generation of peptide fragments for SAR studies and peptide library synthesis.

2. Chiral Amino Acid Intermediate

Bzl-D-Ala-OMe*HCl functions as a chiral amino acid ester intermediate for stereoselective synthesis of D-configured building blocks used in medicinal chemistry and fine chemical manufacturing. The preserved D-stereochemistry at the alpha carbon allows downstream derivatization without racemization during typical ester-to-acid or ester-to-activated-carboxyl conversions, supporting reliable stereochemical outcomes in multistep sequences. The N-benzyl protection strategy provides a stable amine masking group during carboxyl functional-group manipulation, aligning with protecting-group logic used in chiral synthesis planning. The resulting derivatives can be routed toward peptide coupling reagents, protected D-amino acid analogs, or chiral fragments used to construct larger stereodefined molecules.

3. Side-Chain Functionalization

Bzl-D-Ala-OMe*HCl can be applied to side-chain and backbone functionalization strategies that rely on controlled exposure of the amine and carboxyl functionalities. The alanine backbone contains a primary amine protected as benzyl and a methyl ester that can undergo hydrolysis to the corresponding carboxylic acid or conversion to other ester/amide forms, enabling formation of intermediates for further derivatization. The D-configuration influences conformational preferences in peptide-like frameworks, which can be leveraged when generating stereochemically defined analogs for structure-function investigations. Downstream transformations from this intermediate can yield carboxyl-activated species, amide-linked conjugates, or protected D-alanine derivatives compatible with subsequent synthetic elaboration.

4. Pharmaceutical Intermediate Preparation

Bzl-D-Ala-OMe*HCl is suitable for pharmaceutical intermediate preparation where protected amino acid esters serve as feedstocks for controlled assembly of peptidic or peptidomimetic motifs. The N-benzyl protection and methyl ester handle orthogonally during intermediate-stage processing, allowing conversion of the ester into activated carboxyl derivatives while maintaining amine protection until the appropriate stage. The hydrochloride salt form supports practical handling in manufacturing-oriented synthesis planning, particularly when consistent amine protonation states are required for reproducible downstream transformations. The D-alanine stereochemical element can be incorporated into manufacturing routes that generate stereodefined peptide fragments and related intermediates used for process chemistry and specialty chemical production.

5. Analytical Research Standards

Bzl-D-Ala-OMe*HCl can be used in analytical research for method development and reference standard preparation involving protected D-amino acid esters. The combination of benzyl-protected amine and methyl ester creates a defined chemical signature that supports chromatographic separation and mass spectrometric identification of D-alanine-containing intermediates and peptide fragments. The hydrochloride salt form may improve reproducibility in sample preparation and can aid consistent extraction and injection behavior for comparative analyses. Analytical workflows can employ this compound to monitor protection-state changes, verify stereochemical integrity through derivative-based confirmation strategies, and support impurity profiling during peptide building block synthesis and downstream intermediate generation.

1. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review

2. Implications of ligand-receptor binding kinetics on GLP-1R signalling

3. Therapeutic potential of an intestinotrophic hormone, glucagon-like peptide 2, for treatment of type 2 short bowel syndrome rats with intestinal bacterial and fungal dysbiosis

4. The effect of B-type allatostatin neuropeptides on crosstalk between the insect immune response and cold tolerance

5. Identification, Localization in the Central Nervous System and Novel Myostimulatory Effect of Allatostatins in Tenebrio molitor Beetle