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Application Area

DL-Aspartic acid dimethyl ester hydrochloride

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

Category

DL-Amino Acids

Catalog number

BAT-003584

CAS number

14358-33-9

Molecular Formula

C6H11NO4·HCl

Molecular Weight

197.66

DL-Aspartic acid dimethyl ester hydrochloride

IUPAC Name

dimethyl 2-aminobutanedioate;hydrochloride

Synonyms

DL-Asp(OMe)-OMe HCl

Appearance

White or off-white crystal

Purity

≥ 98.5% (Assay: Anhydrous basis)

Melting Point

83-119 °C

Storage

Store at 2-8°C

InChI

InChI=1S/C6H11NO4.ClH/c1-10-5(8)3-4(7)6(9)11-2;/h4H,3,7H2,1-2H3;1H

InChI Key

PNLXWGDXZOYUKB-UHFFFAOYSA-N

Canonical SMILES

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

DL-Aspartic acid dimethyl ester hydrochloride, a versatile chemical compound, finds diverse applications in research and pharmaceutical advancements. Explore four key applications of DL-Aspartic acid dimethyl ester hydrochloride presented with elevated perplexity and burstiness.

Amino Acid Derivative Studies: Delving into the realm of amino acid derivatives, scientists utilize DL-Aspartic acid dimethyl ester hydrochloride to gain profound insights into their chemical characteristics and reactivity. This compound serves as a crucial tool for synthesizing intricate molecules, shedding light on metabolic pathways. It stands as a pivotal model compound for unraveling the mechanisms of amino acid esterification and hydrolysis, offering valuable knowledge for biochemical research.

Peptide Synthesis: Positioned at the heart of peptide synthesis, DL-Aspartic acid dimethyl ester hydrochloride plays a pivotal role as a critical intermediate. It integrates seamlessly into peptide chains, streamlining the creation of specific sequences and complex structures. Scientists harness this compound to craft synthetic peptides tailored for diverse applications, from therapeutic agents to biochemical probes, embodying the essence of precision in molecular design.

Neurochemical Research: In the arena of neurochemical exploration, DL-Aspartic acid dimethyl ester hydrochloride emerges as a key player, unravelling the intricate role of aspartate in the central nervous system. Researchers leverage this compound to delve into neurotransmitter functions and receptor interactions, particularly within excitatory signaling pathways.

Pharmaceutical Formulation: Within pharmaceutical research, DL-Aspartic acid dimethyl ester hydrochloride stands out for its potential as a prodrug in delivering active pharmacological agents. Through chemical modifications, researchers tailor derivatives to enhance the bioavailability and stability of therapeutic compounds, elevating the efficacy of drug formulations. This application underscores the importance of targeted delivery strategies in designing next-generation pharmaceuticals with enhanced performance metrics.

1. Potential inhibitors of L-asparagine biosynthesis. 4. Substituted sulfonamide and sulfonylhydrazide analogues of L-asparagine

S Brynes, G J Burckart, M Mokotoff J Med Chem. 1978 Jan;21(1):45-9. doi: 10.1021/jm00199a008.

Several N-substituted sulfonamides and N'-substituted sulfonylhydrazides have been prepared as sulfur analogues of L-asparagine with the potential of acting as inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma). L-Cysteine was converted in known steps to N-carboxy-3-(sulfonylchloro)-L-alanine dibenzyl ester (1). Condensation of 1 with O-benzylhydroxylamine, p-(fluorosulfonyl)benzylamine, or monoethyl fumarylhydrazide (9), followed by deblocking with HF, gave 3-(hydroxysulfamoyl)-L-alanine (3a), 3-[p-(fluorosulfonylbenzyl)]sulfamoyl-L-alanine (3c), and 3-sulfo-L-alanine S-[2-[(E)-3-(ethoxycarbonyl)acryloyl]hydrazide] (3e), respectively. Similarly, 1 with 2-chloroethylamine and deblocking with H2-Pd gave 3-[(2-chloroethyl)sulfamoyl]-L-alanine (3b). tert-Butyl carbazate was allowed to react with 1 and the tert-butyl group was removed with HCl. The resulting sulfonylhydrazide 7 was condensed with p-(fluorosulfonyl)benzoyl chloride and then deblocked with HF to give 3-sulfo-L-alanine S-[2-[P-(fluorosulfonyl)benzoyl]hydrazide] (3d). The inhibition of ASase by 3a-e at 2 mM was 97, 0, 30, 43, and 37%, respectively, and 3a was competitive with L-aspartic acid. Neither 3a nor 3e was effective in increasing the life span of mice bearing P-388 lymphocytic leukemia.

2. Potential inhibitors of L-asparagine biosynthesis. 3. Aromatic sulfonyl fluoride analogs of L-asparagine and L-glutamine

M Mokotoff, S Brynes, J F Bagaglio J Med Chem. 1975 Sep;18(9):888-91. doi: 10.1021/jm00243a005.

The N-[p-(fluorosulfonyl)benzyl] derivatives of L-asparagine and L-glutamine (1a,b) were synthesized as potential inhibitors of L-asparagine synthetase (ASase). Condensation of p-(fluorosulfonyl)benzylamine (2) with the suitably protected amino acid in the presence of dicyclohexylcarbodiimide, followed by deblocking, afforded 1a and 1b. Derivatives 1a and 1b at 10 mM inhibit ASase isolated from Novikoff hepatoma (rats) by 60 and 46%, respectively. Preliminary results on inhibition of Jensen sarcoma (L-asparaginase sensitive) and JA-1 sarcoma (L-asparaginase resistant) tissue cultures by 0.3 mM 1a (139,90%) and 1b (101, 103%), respectively, are discussed.

3. Potential inhibitors of L-asparagine biosynthesis. 5. Electrophilic amide analogues of (S)-2,3-diaminopropionic acid

M Mokotoff, L W Logue J Med Chem. 1981 May;24(5):554-9. doi: 10.1021/jm00137a015.

Three electrophilic amide analogues of (S)-2,3-diaminopropionic acid (1, DAP) have been prepared as potential inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma, EC 6.3.5.4). DAP was selectively blocked by the carbobenzoxy (Cbz) group to give 3-N-Cbz-DAP (2a). Esterification of 2a with isobutylene afforded tert-butyl 3-N-carbobenzoxy-(S)-2,3-diaminopropionate (3a), which was then blocked at the 2 position with the tert-butoxycarbonyl (Boc) group to give tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-[(carbobenzoxy)amino]propionate (4). Selective cleavage of the Cbz group by H2/Pd gave the key intermediate tert-butyl 2-N-(tert-butoxycarbonyl)-(S)-2,3-diaminopropionate (5), which was acylated, via the N-hydroxysuccinimide esters, with bromoacetic acid, dichloroacetic acid, and fumaric acid monoethyl ester to give tert-butyl 2-[(S)-(tert-butoxycarbonyl)-amino]-3-(2-bromoacetamido)propionate (6a), tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-(2,2-dichloroacetamido)propionate (6b), and tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-(ethoxycarbonyl)acrylamido]-propionate (6c), respectively. Deblocking of 6a-c gave the corresponding amino acids (S)-2-amino-3-(2-bromoacetamido)propionic acid hydrobromide (7a), (S)-2-amino-3-(2,2-dichloroacetamido)propionic acid (7b), and ethyl N-[(S)-2-amino-2-carboxyethyl]fumarate (7c). By a slightly different procedure, 5 was converted in two steps to (S)-2-amino-3-acetamidopropionic acid hydrobromide (7d). The inhibition of ASase by 7a-c at 1 mM was 93, 19, and 37%, respectively, while 7d was without inhibition at 2 mM. Compounds 7a-c failed to increase the life span of mice infected with B16 melanoma.