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L-Alanine methyl ester hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

L-Alanine methyl ester is a derivative of L-Alanine. L-Alanine is used to make in-vivo measurement of glucose and alanine metabolism in studies of patients with diabetes. L-Alanine is a non-essential amino acid for human development and is one of the 20 amino acids encoded by the genetic code.

Category

L-Amino Acids

Catalog number

BAT-003953

CAS number

2491-20-5

Molecular Formula

C4H9NO2·HCl

Molecular Weight

139.60

IUPAC Name

methyl (2S)-2-aminopropanoate;hydrochloride

Synonyms

L-Ala-OMe HCl; L-Alaninemethylesterhydrochloride; L-Alanine Methyl Ester Hydrochloride; (S)-Methyl 2-aminopropanoate hydrochloride; H-Ala-OMe HCl; L-2-amino-propanoic acid methyl ester hydrochloride

Appearance

White powder

Purity

≥ 99% (HPLC)

Melting Point

100-115 °C

Boiling Point

101.5 °C at 760 mmHg

Storage

Store at 2-8 °C

InChI

InChI=1S/C4H9NO2.ClH/c1-3(5)4(6)7-2;/h3H,5H2,1-2H3;1H/t3-;/m0./s1

InChI Key

IYUKFAFDFHZKPI-DFWYDOINSA-N

Canonical SMILES

CC(C(=O)OC)N.Cl

L-Alanine methyl ester hydrochloride, a versatile chemical compound, finds extensive applications in bioscience and pharmaceutical industries. Here are the key applications of L-Alanine methyl ester hydrochloride, presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a pivotal intermediate in peptide synthesis, L-Alanine methyl ester hydrochloride plays a crucial role. Its ester form acts as a protective shield for the amino acid during peptide bond creation, a shield that can be gently removed later. This unique property makes it an invaluable asset in the tailored construction of peptides for both research and therapeutic pursuits.

Pharmaceutical Development: Positioned at the forefront of pharmaceutical innovation, this compound acts as both a precursor and a reagent in synthesizing a diverse array of pharmaceutical agents. It frequently features in the formulation of prodrugs—optimized medications engineered to enhance bioavailability and stability. These derivatives exhibit controlled drug release mechanisms upon entry into the body, heralding a new era in drug development.

Biochemical Research: Within the intricate domain of biochemical research, L-Alanine methyl ester hydrochloride serves as a key player, facilitating exploration of enzyme-substrate interactions and metabolic pathways. Researchers leverage its properties as a substrate analog to delve into enzyme specificity and catalytic mechanisms, unraveling the mysteries of cellular processes and metabolic regulation with each experiment conducted.

Chiral Synthesis: Taking center stage in chiral compound synthesis, L-Alanine methyl ester hydrochloride showcases its prowess in the creation of enantiomerically pure pharmaceuticals. Its chiral center aids in generating stereospecific intermediates, laying the foundation for more potent and selective drugs. This application stands as a cornerstone in the quest for medications with reduced side effects and heightened therapeutic efficacy, propelling pharmaceutical advancements to new heights.

1.Synthesis and activity of HCO-Met-Leu-Phe-OMe analogues containing beta-alanine or taurine at the central position.

Giordano C1, Lucente G, Nalli M, Pagani Zecchini G, Paglialunga Paradisi M, Varani K, Spisani S. Farmaco. 2003 Nov;58(11):1121-30.

New synthetic analogues of the chemotactic N-formyltripeptide HCO-Met-Leu-Phe-OMe have been synthesized. The reported new models, namely Boc-Met-beta-Ala-Phe-OMe (1), HCO-Met-beta-Ala-Phe-OMe (2), Boc-Met-Tau-Phe-OMe (3), HCO-Met-Tau-Phe-OMe (4) and HCl.Met-Tau-Phe-OMe (5), are characterized by the presence at the central position of a residue of beta-alanine or 2-aminoethanesulfonic acid (taurine) replacing the native L-leucine. Whereas tripeptides 1 and 2 have been found quite inactive as chemoattractants, all the three models containing the Tau residue exhibit a remarkable activity. Superoxide anion production and lysozyme release have been also evaluated and the biological results are discussed together with the conformational preferences of the examined models.

2.Galanin stimulates the N-methyl-D-aspartate receptor/nitric oxide/cyclic GMP pathway in vivo in the rat ventral hippocampus.

Consolo S1, Uboldi MC, Caltavuturo C, Bartfai T. Neuroscience. 1998 Aug;85(3):819-26.

We investigated whether the neuropeptide galanin affects the nitric oxide synthase/cyclic GMP pathway in rat hippocampus by measuring in vivo the extracellular cyclic GMP levels during microdialysis. Galanin (2.5 and 3.5 nmol; i.c.v.) dose-dependently raised the extracellular levels of cyclic GMP in the ventral but not the dorsal hippocampus. The effect of 3.5 nmol galanin was blocked by local application of tetrodotoxin and inhibited by the high-affinity galanin antagonist M40 (galanin-[1-12]-Pro3-[Ala-Leu]2-Ala amide). The non-competitive N-methyl-D-aspartate receptor antagonist dizocilpine maleate (30 microM infused into the ventral hippocampus or 0.2 mg/kg, i.p.) and the competitive one, 3-([R]-carboxypiperazin-4-yl)-propyl-phosphonic acid (50 microM infused), but not local perfusion of the AMPA antagonist 6-nitro-7-sulphamoylbenzo(f)quinoxaline-2,3-dione (15 microM) abolished the galanin-evoked cyclic GMP response in the hippocampus.