Methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride is a dipeptidyl methyl ester derived from alanine, useful as a chiral building block. The protonated amino group enhances solubility, while the ester allows controlled hydrolysis or coupling. Researchers study its conformational preferences and reactivity in peptide synthesis. Applications include fragment assembly, stereochemical probes, and linker design.
CAT No: R2378
CAS No:41036-19-5
Synonyms/Alias:methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride;41036-19-5;H-ALA-ALA-OME HCL;(S)-Methyl 2-((S)-2-aminopropanamido)propanoate hydrochloride;H-Ala-Ala-OMe.HCl;H-Ala-Ala-OMe hydrochloride;methyl (2S)-2-[(2S)-2-aminopropanamido]propanoate hydrochloride;methyl (2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoate;hydrochloride;methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride;MFCD00237711;H-Ala-Ala-OMe . HCl;SCHEMBL3883130;DTXSID00553440;BS-28147;E78489;EN300-100802;Methyl L-alanyl-L-alaninate--hydrogen chloride (1/1);831-614-4;
Methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride represents a specialized carbohydrate-related compound widely utilized in biochemical and pharmaceutical research. Characterized by its well-defined stereochemistry and functional groups, this molecule serves as a valuable intermediate in synthetic pathways, particularly those requiring amino acid derivatives. The hydrochloride salt form enhances its solubility and stability, making it suitable for a variety of laboratory and industrial applications. Its unique structure, which incorporates both methyl ester and amide functionalities, allows for versatile reactivity and compatibility with diverse chemical processes. Researchers often select this compound for its ability to facilitate peptide coupling reactions, as well as its role in the synthesis of more complex molecules. The adaptability of methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride to different reaction conditions further underscores its importance in modern synthetic chemistry.
Peptide Synthesis: Within the realm of peptide synthesis, methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride acts as a protected amino acid derivative, streamlining the assembly of peptide chains. Its methyl ester group can be selectively removed under mild conditions, enabling sequential addition of amino acids with high fidelity. This property is particularly advantageous when constructing peptides with precise sequence requirements, as it minimizes side reactions and racemization. Researchers leverage its reactivity to enhance coupling efficiency and improve the overall yield of target peptides, making it a staple in both manual and automated peptide synthesis protocols.
Pharmaceutical Intermediates: As a pharmaceutical intermediate, this compound plays a pivotal role in the development of novel drug candidates. Its amide and ester functionalities provide reactive handles for further chemical modifications, allowing medicinal chemists to generate libraries of analogs for structure-activity relationship studies. By incorporating this intermediate into synthetic routes, researchers can efficiently introduce functional diversity into lead compounds, accelerating the optimization process for therapeutic agents. Its compatibility with a wide range of reagents and reaction conditions supports its use in complex multistep syntheses, contributing to the advancement of drug discovery efforts.
Chiral Building Block: The stereochemical integrity of methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride makes it an attractive chiral building block for asymmetric synthesis. Its well-defined configuration can be transferred to downstream products, facilitating the creation of enantiomerically pure compounds. In the context of asymmetric catalysis or the construction of chiral centers, this molecule enables the synthesis of optically active intermediates that are essential for the production of biologically relevant molecules. Chemists exploit its chirality to streamline synthetic routes and achieve high enantioselectivity in target compounds.
Chemical Biology Research: In chemical biology, methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride is often utilized as a probe or precursor for the study of enzyme mechanisms and protein interactions. Its structural resemblance to natural amino acid derivatives allows it to be incorporated into peptides or small molecules that modulate biological processes. By serving as a substrate or inhibitor in enzymatic assays, it aids in elucidating the function of key biomolecules and in identifying potential targets for intervention. Its versatility in labeling and conjugation strategies further expands its utility in the exploration of complex biological systems.
Material Science Applications: Beyond its traditional roles in synthesis and biology, this compound finds utility in material science, particularly in the design of functionalized polymers and biomaterials. Its amide and ester groups facilitate covalent attachment to polymer backbones, enabling the creation of materials with tailored properties such as biocompatibility or controlled degradation. Researchers exploit these features to develop advanced materials for applications ranging from drug delivery systems to tissue engineering scaffolds. The structural versatility and reactivity of methyl (2S)-2-((2S)-2-aminopropanamido)propanoate hydrochloride thus make it a valuable component in the interdisciplinary field of materials innovation.
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