L-Aspartic acid β-methyl ester hydrochloride
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L-Aspartic acid β-methyl ester hydrochloride

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L-Aspartic acid 4-methyl ester is a protected form of L-Aspartic acid. L-Aspartic acid is a non-essential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system.

Category
L-Amino Acids
Catalog number
BAT-004120
CAS number
16856-13-6
Molecular Formula
C5H9NO4.HCl
Molecular Weight
183.59
L-Aspartic acid β-methyl ester hydrochloride
IUPAC Name
(2S)-2-amino-4-methoxy-4-oxobutanoic acid;hydrochloride
Synonyms
L-Aspartic acid, 4-methyl ester, hydrochloride (1:1); L-Aspartic acid, 4-methyl ester, hydrochloride; Aspartic acid, 4-methyl ester, hydrochloride, L-; (S)-2-Amino-4-methoxy-4-oxobutanoic acid hydrochloride; L-Aspartic acid β-methyl ester monohydrochloride; β-Methyl L-aspartate hydrochloride
Related CAS
2177-62-0 (free base)
Appearance
White crystalline powder
Purity
≥95%
Melting Point
190°C
Storage
Store at 2-8°C
InChI
InChI=1S/C5H9NO4.ClH/c1-10-4(7)2-3(6)5(8)9;/h3H,2,6H2,1H3,(H,8,9);1H/t3-;/m0./s1
InChI Key
QRBMPUYOGOCYDJ-DFWYDOINSA-N
Canonical SMILES
COC(=O)CC(C(=O)O)N.Cl

L-Aspartic acid β-methyl ester hydrochloride is a chemical compound derived from aspartic acid, an amino acid prevalent in the biosynthesis of proteins. This compound is particularly noted for its unique chemical structure, which includes a β-methyl ester group. The methyl ester modification endows the molecule with distinct properties, making it crucial in various chemical and biological applications. Moreover, the hydrochloride salt form enhances its solubility in water, facilitating its use in aqueous solutions. Its stereochemistry, being an L-isomer, aligns structurally with many biologically active molecules, which is significant in medicinal chemistry and biochemistry applications. At a fundamental level, L-Aspartic acid β-methyl ester hydrochloride serves as an essential intermediate in synthetic organic chemistry, providing a versatile building block for further chemical transformations.

One of the primary applications of L-Aspartic acid β-methyl ester hydrochloride is in the field of pharmaceuticals. Due to its structural similarity to neurotransmitters and its ability to mimic biological compounds, it is frequently used in the synthesis of biologically active molecules, particularly in the development of new drug candidates. It can act as a precursor in the preparation of a variety of pharmacologically relevant compounds, including amino acid derivatives that may modulate neurological pathways. Its role in drug synthesis emphasizes the importance of precise stereochemistry in the pharmaceutical industry, where even slight structural changes can significantly alter biological activity and efficacy.

In addition to pharmaceuticals, L-Aspartic acid β-methyl ester hydrochloride plays a critical role in peptide synthesis. Peptides are crucial in many biological processes and have therapeutic potential in treating diseases. The compound’s ester form allows it to be used as a protected amino acid derivative, facilitating the stepwise synthesis of peptides by preventing side reactions that may occur during peptide bond formation. This protection strategy is vital in laboratory and industrial settings, where the efficiency and yield of peptide synthesis are of utmost importance. It contributes to the production of complex peptides used in research and as therapeutic agents.

Another key application area for L-Aspartic acid β-methyl ester hydrochloride is in chemical research and development. As an intermediate, it enables the creation of novel compounds with potentially diverse chemical and physical properties. Research chemists utilize this compound to explore the synthesis of new materials, where its functional groups can undergo various chemical reactions such as alkylation or acylation. These chemical transformations are foundational in developing new materials, catalysts, and ligands used in industrial processes and academic research, leading to innovations in material science and engineering.

Furthermore, L-Aspartic acid β-methyl ester hydrochloride serves a significant role in the agricultural sector, especially in the synthesis of agrochemicals. These chemicals are critical in enhancing crop yield and protection. The compound can be utilized in designing and synthesizing herbicides and pesticides, taking advantage of its ability to interfere with biological processes in pests and weeds. By enabling the development of more effective and selective agrochemicals, it supports sustainable agricultural practices and contributes to meeting global food production demands. This application underscores the compound’s versatility and importance in addressing contemporary challenges in food security and sustainable agriculture.

1. A novel 1 beta-methylcarbapenem antibiotic, S-4661. Synthesis and structure-activity relationships of 2-(5-substituted pyrrolidin-3-ylthio)-1 beta-methylcarbapenems
Y Iso, T Irie, Y Nishino, K Motokawa, Y Nishitani J Antibiot (Tokyo). 1996 Feb;49(2):199-209. doi: 10.7164/antibiotics.49.199.
The synthesis and biological activity of (1R,5S,6S)-2-[(3S,5S)-5-substituted pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1- methylcarbapen-2-em-3-carboxylic acids are described. These compounds exhibit potent antibacterial activity against a wide range of both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. Of these new carbapenems, (1R,5S,6S)-2-[(3S,5S)-5-sulfamoylaminomethyl pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarb apen- 2-em-3-carboxyli c acid (S-4661) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.
2. Facile synthesis of (R)-4-mercaptopyrrolidine-2-thione from L-aspartic acid
M Seki, T Shimizu Biosci Biotechnol Biochem. 2001 Apr;65(4):973-6. doi: 10.1271/bbb.65.973.
An SN2-type of substitution of (S)-bromide 4, which had been prepared from L-aspartic acid, with potassium thiobenzoate provided (R)-benzoylthio derivative 5 with complete inversion of the configuration. Compound 5 was converted, via iodide 6c, to (R)-4-amino-3-benzoylthiobutyric acid 8b. (R)-4-Mercapto pyrrolidine-2-thione 1 was readily obtained from 8b through cyclization with acetic anhydride, thionation with Lawesson's reagent and facile removal of the S-benzoyl group with sodium methoxide.
3. Practical synthesis of a 1beta-methylcarbapenem, J-111,225, using 4-mercapto-2-[4-(N-methylaminomethyl)phenyl]pyrrolidine as a precursor
H Imamura, A Shimizu, H Sato, Y Sugimoto, S Sakuraba, K Yamada, H Morishima Chem Pharm Bull (Tokyo). 2001 Apr;49(4):476-9. doi: 10.1248/cpb.49.476.
An effective and practical procedure for the synthesis of J-111,225 (1), a new 1beta-methylcarbapenem, was developed using 4-mercapto-2-14-(N-methylaminomethyl)phenyl]pyrrolidine (2a) as a precursor. The coupling reaction of 2a with p-nitrobenzyl (PNB)-protected 1beta-methylcarbapenem enolphosphate 3a and successive removal of PNB group afforded J-111,225 (1) in significantly increased yield compared to the ordinary procedure using a C-2 side-chain thiol with amino-protective groups.
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