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• 3. Synthesis and biological evaluation of zinc chelating compounds as metallo-β-lactamase inhibitors
  Geir Kildahl-Andersen,Christian Schnaars,Anthony Prandina,Sylvie Radix,Marc Le Borgne,Lars Petter Jordheim,Tor Gj?en,Adriana Magalh?es Santos Andresen,Silje Lauksund,Christopher Fr?hlich,?rjan Samuelsen,P?l Rongved,Ove Alexander H?gmoen ?strand Med. Chem. Commun. 2019 10 528
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to H-D-Ala-OMe hydrochloride (CAS No. 14316-06-4) in Modern Chemical and Pharmaceutical Research

H-D-Ala-OMe hydrochloride, chemically known as N-(α-methoxyethyl)-L-alanine hydrochloride, is a compound of significant interest in the field of chemical and pharmaceutical research. With a CAS number of 14316-06-4, this molecule has found applications in various biochemical studies, peptidomimetics, and drug development pipelines. Its unique structural features, comprising an alanine backbone modified with a methoxyethyl group and a hydrochloride salt form, make it a versatile building block for synthetic chemists and biologists alike.

The structure of H-D-Ala-OMe hydrochloride is characterized by a chiral L-alanine residue, which contributes to its stereochemical properties. The methoxyethyl group at the amino terminus introduces hydrophobicity and influences the compound's solubility and interactions with biological targets. The hydrochloride salt form enhances its stability and bioavailability, making it particularly useful in pharmaceutical formulations. This combination of features has positioned H-D-Ala-OMe hydrochloride as a key intermediate in the synthesis of more complex molecules.

In recent years, advancements in peptidomimetic chemistry have highlighted the importance of H-D-Ala-OMe hydrochloride as a scaffold for designing novel therapeutic agents. Peptidomimetics are designed to mimic the bioactivity of natural peptides while avoiding their limitations, such as susceptibility to enzymatic degradation. The incorporation of H-D-Ala-OMe hydrochloride into peptidomimetic sequences can enhance binding affinity, improve pharmacokinetic profiles, and reduce immunogenicity. For instance, studies have demonstrated its utility in developing protease inhibitors and receptor antagonists.

One of the most compelling applications of H-D-Ala-OMe hydrochloride is in the field of cancer research. Researchers have leveraged its structural motifs to create targeted therapies that interact with specific oncogenic pathways. The methoxyethyl group serves as a linker that can be further functionalized to attach cytotoxic agents or targeting moieties. Preclinical studies have shown promising results in using derivatives of H-D-Ala-OMe hydrochloride to inhibit tumor growth and induce apoptosis in various cancer models. These findings underscore the compound's potential as a lead compound for oncology drug discovery.

The role of H-D-Ala-OMe hydrochloride in drug development extends beyond oncology. It has been explored in the treatment of neurodegenerative diseases, where peptide-based therapies are increasingly recognized for their therapeutic potential. The ability to modulate peptide stability and bioavailability through modifications like the methoxyethyl group makes H-D-Ala-OMe hydrochloride an attractive candidate for designing neuroprotective agents. Recent research has focused on its use in developing treatments for Alzheimer's disease and Parkinson's disease, where peptide-based drugs are being investigated for their ability to modulate neural signaling pathways.

Another emerging area where H-D-Ala-OMe hydrochloride is making strides is in antimicrobial research. The rise of antibiotic-resistant bacteria has necessitated the development of novel antimicrobial agents with unique mechanisms of action. Peptidomimetics derived from H-D-Ala-OMe hydrochloride have shown promise in disrupting bacterial cell wall synthesis and inhibiting pathogenic enzymes. These derivatives offer an alternative to traditional antibiotics by targeting conserved bacterial pathways that are less prone to resistance evolution. Such innovations highlight the compound's versatility and its potential contribution to combating antimicrobial resistance.

The synthetic methodologies for preparing H-D-Ala-OMe hydrochloride have also seen significant advancements. Modern synthetic techniques allow for high-yield production with minimal side reactions, ensuring purity and consistency required for pharmaceutical applications. Continuous flow chemistry, for instance, has been employed to streamline the synthesis process while maintaining scalability. These improvements not only enhance production efficiency but also reduce costs associated with manufacturing peptide-based therapeutics.

The analytical characterization of H-D-Ala-OMe hydrochloride is equally critical for ensuring its quality and efficacy. Techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC) are routinely used to confirm molecular structure and assess purity. Advanced spectroscopic methods like circular dichroism (CD) spectroscopy provide insights into the conformational properties of peptides derived from this compound, which is essential for understanding their biological activity.

In conclusion, H-D-Ala-OMe hydrochloride (CAS No. 14316-06-4) represents a cornerstone molecule in modern chemical and pharmaceutical research. Its structural versatility, combined with its stability and bioavailability, makes it an invaluable tool for drug discovery across multiple therapeutic areas. From peptidomimetics to cancer therapeutics and antimicrobial agents, the applications of derivatives derived from this compound continue to expand. As research progresses, it is likely that new innovative uses will emerge, further solidifying its role as a pivotal compound in medicinal chemistry.

• 2491-20-5(L-Alanine methyl ester hydrochloride)
• 13515-97-4(H-DL-Ala-OMe.HCl)
• 617-27-6(D,L-Alanine Ethyl Ester Hydrochloride)
• 16115-80-3(Dimethyl aminomalonate hydrochloride)
• 1115-59-9(H-Ala-OEt.HCl)
• 5619-04-5(methyl 2-amino-3-hydroxypropanoate hydrochloride)
• 5680-80-8(L-Serine methyl ester hydrochloride)
• 5874-57-7(H-D-Ser-OMe.HCl)
• 10065-72-2((S)-Methyl 2-aminopropanoate)
• 125511-26-4(Alanine, propyl ester)