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β-Alanine methyl ester hydrochloride

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β-Alanine Methyl Ester is an intermediate in the synthesis of Trichostatin A and Trapoxin B as histone deacetylase inhibitors.

Category

Inhibitors containing Unusual Amino Acids

Catalog number

BAT-007609

CAS number

3196-73-4

Molecular Formula

C4H9NO2·HCl

Molecular Weight

139.62

IUPAC Name

methyl 3-aminopropanoate;hydrochloride

Synonyms

β-Ala-OMe HCl; Methyl 3-aminopropanoate Hydrochloride; beta-Alanine methyl ester hydrochloride; h-beta-ala-ome hydrochloride; beta-alanine methyl ester HCl; 3-aminopropanoic acid methyl ester hydrochloride; Methyl beta-alaninate hydrochloride; 3-aminopropionic acid methyl ester hydrochloride

Related CAS

4138-35-6 (free base)

Appearance

White crystalline powder

Purity

≥ 98% (HPLC)

Density

1.013 g/cm3

Melting Point

103-105 °C

Boiling Point

151.8 °C at 760 mmHg

Storage

Store at 2-8 °C

InChI

InChI=1S/C4H9NO2.ClH/c1-7-4(6)2-3-5;/h2-3,5H2,1H3;1H

InChI Key

XPGRZDJXVKFLHQ-UHFFFAOYSA-N

Canonical SMILES

COC(=O)CCN.Cl

β-Alanine methyl ester hydrochloride, a potent chemical compound utilized in biochemical and physiological exploration, finds diverse applications with high perplexity and burstiness. Here are the key applications:

Performance Enhancement Studies: In the realm of research, β-Alanine methyl ester hydrochloride emerges as a pivotal tool for investigating its impact on muscle endurance and performance. Serving as a precursor to carnosine, a vital buffer for lactic acid in muscles, this compound aids in mitigating fatigue during high-intensity exercise. Researchers delve into this compound to unravel potential ergogenic aids crucial for enhancing athletes' capabilities.

Neuroscience Research: Delving into the enigmatic realm of neuroscience, β-Alanine methyl ester hydrochloride shines as a subject of exploration for its potential neuroprotective properties. Scientists probe into its abilities to modulate neurotransmitter release and synaptic plasticity, aiming to unravel novel strategies for combating neurodegenerative conditions. By deciphering its effects on the nervous system, researchers pave the way for groundbreaking approaches to neuroprotection.

Protein Synthesis Studies: At the forefront of protein synthesis studies, β-Alanine methyl ester hydrochloride plays a pivotal role in unraveling the mysteries of amino acid metabolism. As a derivative of β-alanine, this compound aids researchers in deciphering how alterations in the amino acid pool influence muscle protein synthesis. This research serves as a cornerstone for developing innovative nutritional supplements and comprehending the intricate mechanisms driving muscle growth.

Biochemical Assays: Within the realm of biochemical research, β-Alanine methyl ester hydrochloride acts as a versatile substrate and reagent in a myriad of assays. Researchers leverage its properties to delve into enzyme kinetics, reaction mechanisms, and cellular uptake processes. By harnessing this compound in controlled experiments, scientists gain profound insights into fundamental biochemical pathways and enzyme functions, paving the way for groundbreaking discoveries in biochemistry.

1.Improved synthesis and resolution of beta-(3-pyridyl)-DL-alpha-alanine.

Folkers K, Kubiak T, Stepinski J. Int J Pept Protein Res. 1984 Sep;24(3):197-200.

beta-Benzamido-alpha-(3-pyridyl)-DL-alpha-alanine hydrochloride was synthesized from 3-pyridinecarboxyaldehyde via the azlactone which was hydrolyzed to the acrylic acid before hydrogenation. The methyl ester was effectively resolved with subtilisin. The optical purity of the D-isomer was established, since the D-isomer was used in synthesis of antagonists of the luteinizing hormone releasing hormone.

2.Temperature dependence of rotational disorder in a non-standard amino acid from X-ray crystallography and molecular dynamics simulation.

Dittrich B1, Warren JE, Fabbiani FP, Morgenroth W, Corry B. Phys Chem Chem Phys. 2009 Apr 21;11(15):2601-9. doi: 10.1039/b819157c. Epub 2009 Feb 20.

The X-ray single-crystal structure of methyl 2-aminoisobutyrate hydrochloride (Me-AIB), a non-standard amino acid, is reported at 10, 30, 50, 70 and 100 K. Fourier maps indicate the presence of rotational disorder of the hydrogen atoms of the ester methyl group. To study this effect in detail, high resolution data were collected with synchrotron radiation. The non-spherical molecular electron density was predicted with invariom scattering factors and subtracted from the density obtained from a full multipole refinement. This allows disorder to be distinguished from the molecular electron density at each temperature. The disorder is reduced between 100 K and 30 K, but still detectable even at 10 K. Hence, difference densities can be applied for the purpose of electronic structure validation and have the advantage of an absence of noise over Fourier methods. Ultra-low temperature experiments are foreseen to be useful in reducing such kinds of disorder in ultra-high resolution protein crystallography.

3.Differential effect of 2-aminoethyl-isothiourea, an inhibitor of the inducible nitric oxide synthase, on microvascular blood flow and organ injury in models of hepatic ischemia-reperfusion and endotoxemia.

Wang Y1, Lawson JA, Jaeschke H. Shock. 1998 Jul;10(1):20-5.

The vasodilator nitric oxide (NO) is involved in the regulation of systemic blood pressure and local organ blood flow. Inhibitors of the constitutively expressed nitric oxide synthase in endothelial cells (eNOS), e.g., Nomega-nitro-L-arginine methyl ester hydrochloride (L-NAME), aggravated liver injury in a variety of models. On the other hand, inhibitors of the inducible NOS (iNOS), e.g., 2-aminoethyl-isothiourea (AET), were found to be beneficial during endotoxemia. The aim of this investigation was to study the effect of AET compared with L-NAME on liver microvascular blood flow and injury in more complex models with multiple insults, i.e., ischemia (20 min)-reperfusion (8 h) in combination with .5 mg/kg endotoxin (IRE). Male Fisher rats were treated with 10 mg/kg AET or L-NAME and subjected to IRE. At 8 h, liver injury (plasma ALT: 1320+/-164 U/L) was significantly increased in AET-treated (5,018+/-1,379 U/L) and L-NAME-treated groups (2,429+/-228 U/L).

4.New insights into the mechanism of neurolathyrism: L-β-ODAP triggers [Ca2+]i accumulation and cell death in primary motor neurons through transient receptor potential channels and metabotropic glutamate receptors.

Kusama-Eguchi K1, Miyano T2, Yamamoto M3, Suda A2, Ito Y4, Ishige K4, Ishii M5, Ogawa Y2, Watanabe K2, Ikegami F6, Kusama T7. Food Chem Toxicol. 2014 May;67:113-22. doi: 10.1016/j.fct.2014.02.021. Epub 2014 Feb 25.

Neurolathyrism is a motor neuron (MN) disease caused by β-N-oxalyl-L-α,β-diaminopropionic acid (L-β-ODAP), an AMPA receptor agonist. L-β-ODAP caused a prolonged rise of intracellular Ca(2+) ([Ca(2+)]i) in rat spinal cord MNs, and the [Ca(2+)]i accumulation was inversely proportional to the MN's life span. The [Ca(2+)]i rise induced by L-β-ODAP or (S)-AMPA was antagonized completely by NBQX, an AMPA-receptor blocker. However, blocking the L-type Ca(2+) channel with nifedipine significantly lowered [Ca(2+)]i induced by (S)-AMPA, but not that by L-β-ODAP. Tetrodotoxin completely extinguished the [Ca(2+)]i rise induced by (S)-AMPA or kainic acid, whereas that induced by L-β-ODAP was only attenuated by 65.6±6% indicating the prominent involvement of voltage-independent Ca(2+) entry. The tetrodotoxin-resistant [Ca(2+)]i induced by L-β-ODAP was blocked by 2-APB, Gd(3+), La(3+), 1-(β-[3-(4-methoxy-phenyl)propoxy]-4-methoxyphenethyl)-1H-imidazole hydrochloride (SKF-96365) and flufenamic acid, which all are blockers of the transient receptor potential (TRP) channels.