b-Cyclohexyl-L-alanine methyl ester hydrochloride
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b-Cyclohexyl-L-alanine methyl ester hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-007905
CAS number
144600-01-1
Molecular Formula
C10H19NO2·HCl
Molecular Weight
221.72
b-Cyclohexyl-L-alanine methyl ester hydrochloride
IUPAC Name
methyl 2-amino-3-cyclohexylpropanoate;hydrochloride
Synonyms
H-Cha-OMe HCl; Methyl 2-amino-3-cyclohexylpropanoate hydrochloride; H-beta-Cyclohexyl-Ala-OMe HCl; Methyl 2-amino-3-cyclohexylpropanoate HCl
Purity
≥ 99% (HPLC)
Melting Point
153-159 °C
Storage
Store at 2-8 °C
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
InChI Key
YLESODBCBYZUCT-UHFFFAOYSA-N
Canonical SMILES
COC(=O)C(CC1CCCCC1)N.Cl

b-Cyclohexyl-L-alanine methyl ester hydrochloride, a versatile chemical with diverse applications in bioscience and pharmacology. Here are the key applications presented with high perplexity and burstiness:

Chiral Synthesis: Widely utilized as a chiral building block, b-Cyclohexyl-L-alanine methyl ester hydrochloride plays a pivotal role in synthesizing enantiomerically pure compounds. This compound is indispensable for crafting pharmaceuticals with specific chiral centers, profoundly influencing a drug's efficacy and safety. By ensuring the desired stereochemistry of target compounds, this compound underscores their biological activity and therapeutic potential.

Peptide Synthesis: In the realm of peptide chemistry, b-Cyclohexyl-L-alanine methyl ester hydrochloride serves as a protected amino acid derivative, facilitating the construction of peptides with intricate sequences. By thwarting undesired side reactions during synthesis, this compound streamlines the assembly process, culminating in high-purity peptide products. Researchers leverage this compound to achieve precision and excellence in peptide synthesis endeavors.

Drug Development: A cornerstone in peptide-based drug development, b-Cyclohexyl-L-alanine methyl ester hydrochloride enhances the stability and bioavailability of therapeutic peptides. Its incorporation into peptide sequences elevates the effectiveness of these drugs in clinical settings. Empowered by this compound, researchers can engineer peptides with optimized pharmacokinetic properties and heightened therapeutic efficacy, reshaping the landscape of modern medicine.

Molecular Probes: Scientists harness b-Cyclohexyl-L-alanine methyl ester hydrochloride to craft molecular probes for investigating protein-ligand interactions. These probes serve as invaluable tools in elucidating binding mechanisms and pinpointing crucial residues involved in receptor modulation. In the realm of drug discovery, understanding these intricate interactions is paramount, as it could pave the way for groundbreaking advancements in therapeutic development and clinical interventions.

1. The Effects of Irisin on Nω-Nitro-L-arginine Methyl Ester Hydrochloride-Induced Hypertension in Rats
Nurettin Aydoğdu, Özlem Yalçınkaya Yavuz, Ebru Taştekin, Pınar Tayfur, Oktay Kaya, Nihayet Kandemir Balkan Med J. 2019 Oct 28;36(6):337-346. doi: 10.4274/balkanmedj.galenos.2019.2019.5.113. Epub 2019 Sep 5.
Background: The cause of about 95% of hypertension, an important public health problem, is unknown. Intensive studies are underway to understand the physiopathology of hypertension. Irisin, a newly discovered hormone, has been reported to dilate vascular smooth muscle and lower blood pressure acutely. Aims: To investigate the effects of chronic irisin treatment on blood pressure and renal functions in a hypertension model established by nitric oxide synthase inhibition by treatment with Nω-nitro-L-arginine methyl ester hydrochloride. Study design: Animal experimentation. Methods: Male Sprague-Dawley rats were divided into four groups (n=8). Control and irisin groups received an intravenous saline injection, hypertension and hypertension + irisin (hypertension + irisin) groups received 1.5 mg/100 g Nω-nitro-L-arginine methyl ester hydrochloride. Nω-nitro-L-arginine methyl ester hydrochloride (150 mg/L) was added to the drinking water of rats in groups hypertension and hypertension + irisin for three weeks. In the second week of the experiment, irisin (50 nmol/day) was given to rats in groups irisin and hypertension + irisin, and saline was administered to rats in groups control and hypertension for two weeks through subcutaneously placed osmotic minipumps. Blood pressure was measured by the tail-cuff plethysmography method. On the twenty-first day of the experiment, 24-hour urine, blood, and both kidneys of the rats were collected. Results: The hypertension group had elevated systolic, diastolic, and mean arterial blood pressure values compared with the control group, with decreased glutathione levels in tissue and serum, but an increase in serum oxidized glutathione level (p<0.05). Histopathologically, increased tubular injury, cast formation, glomerular sclerosis, and peritubular fibrosis levels were observed (p<0.05). Irisin treatment did not cause any significant change in blood pressure, renal functions, and injury scores. However, renal nitric oxide levels significantly increased, and endothelial nitric oxide synthase immunoreactivity was determined to be reduced (p<0.05). Conclusion: Treatment with chronic irisin at a physiological dose does not reduce blood pressure in an experimental model of hypertension. In different models of experimental hypertension, the effects of irisin administration at different doses and at different periods should be thoroughly investigated.
2. l-Alanine methyl ester hydro-chloride monohydrate
Martin Lutz, Arie Schouten Acta Crystallogr Sect E Struct Rep Online. 2011 Feb 9;67(Pt 3):o586. doi: 10.1107/S160053681100420X.
The enanti-opure title compound, C(4)H(10)NO(2) (+)·Cl(-)·H(2)O, forms a two-dimensional network by inter-molecular hydrogen bonding parallel to (010). Non-merohedral twinning with a twofold rotation about the reciprocal c* axis as twin operation was taken into account during intensity integration and structure refinement. This twinning leads to alternative orientations of the stacked hydrogen-bonded layers.
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