β-Cyclohexyl-L-alanine methyl ester hydrochloride
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β-Cyclohexyl-L-alanine methyl ester hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-007535
CAS number
17193-39-4
Molecular Formula
C10H20ClNO2
Molecular Weight
221.73
β-Cyclohexyl-L-alanine methyl ester hydrochloride
IUPAC Name
methyl (2S)-2-amino-3-cyclohexylpropanoate;hydrochloride
Synonyms
H-Cha-OMe HCl; H-Phe(hexahydro)-OMe HCl; Hexahydro-L-phenylalanine methyl ester hydrochloride; (S)-Methyl 2-amino-3-cyclohexylpropanoate hydrochloride; H-CHA-OME HCl; beta-Cyclohexyl-L-alanine methyl ester hydrochloride; methyl 3-cyclohexylalaninate hydrochloride; methyl (2S)-2-amino-3-cyclohexylpropanoatehydrochloride; H Cha OMe HCl
Purity
≥ 98%
InChI
InChI=1S/C10H19NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h8-9H,2-7,11H2,1H3;1H/t9-;/m0./s1
InChI Key
YLESODBCBYZUCT-FVGYRXGTSA-N
Canonical SMILES
COC(=O)C(CC1CCCCC1)N.Cl

β-Cyclohexyl-L-alanine methyl ester hydrochloride is extensively utilized in the pharmaceutical industry as a crucial compound in drug research and development. Its unique molecular characteristics provide an advantageous starting point for the synthesis of novel therapeutic agents. By leveraging its chemical structure, researchers are able to design and optimize new pharmaceutical compounds with improved efficacy and selectivity. This amino acid derivative plays a vital role in structure-activity relationship (SAR) studies, which are essential for understanding how modifications to the molecular framework influence biological activity. Therefore, its application in drug discovery helps in the identification and refinement of potential drug candidates targeting a wide array of medical conditions, thereby accelerating the development of effective medications.

In the field of peptide synthesis, β-Cyclohexyl-L-alanine methyl ester hydrochloride serves as a building block for creating peptides that mimic naturally occurring proteins. This amino acid derivative is particularly valued for its ability to introduce specific structural and functional properties into synthetic peptides. Such customization is pivotal when designing peptides for therapeutic use, including enzyme inhibitors, receptor agonists, and antimicrobial agents. The introduction of the cyclohexyl group into peptides can enhance their stability, bioavailability, and resistance to proteolytic degradation, which are critical factors in the development of peptide-based drugs. By contributing to the synthesis of novel peptides, this compound aids in expanding the therapeutic potential and diversity of peptide drugs.

β-Cyclohexyl-L-alanine methyl ester hydrochloride is also instrumental in analytical chemistry, particularly in the characterization and quantification of chiral substances. Its specific stereochemistry is used as an enantiomeric reference standard in chiral chromatography techniques, such as high-performance liquid chromatography (HPLC). This application is vital for the separation and analysis of enantiomers in complex mixtures, which is of paramount importance in pharmaceutical quality control and assurance. The ability to distinguish and accurately measure the enantiomeric purity of pharmaceutical compounds ensures their safety and efficacy, as different enantiomers of a drug can exhibit significantly different biological activities and side effects.

β-Cyclohexyl-L-alanine methyl ester hydrochloride finds significant application in biochemistry and molecular biology research as a model compound for studying protein structure and function. Due to its resemblance to natural amino acids, it can be incorporated into proteins and peptides to investigate the effects of side-chain modifications on protein stability, folding, and function. Researchers utilize this amino acid derivative to probe the interaction dynamics within proteins, aiding in the elucidation of mechanisms underlying protein biosynthesis and degradation. The insights gained from such studies are instrumental in advancing our understanding of various biological processes and can contribute to the development of biotechnological applications, such as enzyme engineering and protein-based therapeutics.

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