16856-13-6

Basic information

• Product Name: beta-Methyl L-aspartate hydrochloride
• Synonyms: H-ASP(OME)-OH HCL;ASPARTIC ACID(OME)-OH HCL;beta-Methyl L-aspartate hydrochloride;l-asparitc acid 4-methyl ester hydrochloride;L-ASPARTIC ACID B-METHYL ESTER HCL;L-ASPARTIC ACID B-METHYL ESTER HYDROCHLORIDE;L-ASPARTIC ACID BETA-METHYL ESTER HCL;L-ASPARTIC ACID BETA-METHYL ESTER HYDROCHLORIDE
• CAS NO: 16856-13-6
• Molecular Formula: C₅H₉NO₄*ClH
• Molecular Weight: 183.59
• EINECS: 240-880-5
• Product Categories: Aspartic acid [Asp, D];Amino Acids and Derivatives;Amino hydrochloride;A - H;Amino Acids;Modified Amino Acids
• Mol File: 16856-13-6.mol

Chemical Properties

• Melting Point: 191-193°C
• Boiling Point: 301.7 °C at 760mmHg
• Flash Point: 136.3 °C
• Appearance: /Solid
• Density: 1.299g/cm3
• Vapor Pressure: 0.000242mmHg at 25°C
• Storage Temp.: −20°C
• CAS DataBase Reference: beta-Methyl L-aspartate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: beta-Methyl L-aspartate hydrochloride(16856-13-6)
• EPA Substance Registry System: beta-Methyl L-aspartate hydrochloride(16856-13-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 16856-13-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Beta-Methyl L-aspartate hydrochloride is used as an intermediate in the synthesis of various pharmaceutical compounds for its role in the biosynthesis of amino acids and its impact on neuronal function.
Used in Neurological Applications:
Beta-Methyl L-aspartate hydrochloride is used as a neurochemical agent for its ability to increase membrane conductance in mammalian neurons, causing depolarization and nerve impulses that can be beneficial in the treatment of certain neurological conditions.
Used in Research and Development:
Beta-Methyl L-aspartate hydrochloride is used as a research compound to study the effects of L-Aspartic acid on neuronal function and amino acid biosynthesis, contributing to the advancement of neuroscience and pharmaceutical development.
Used in Drug Delivery Systems:
Similar to gallotannin, beta-Methyl L-aspartate hydrochloride can be employed in drug delivery systems to improve its bioavailability and therapeutic outcomes. Various organic and metallic nanoparticles can be used as carriers for its delivery, targeting specific areas of the central nervous system for enhanced efficacy.

Purification Methods

Recrystallise it from MeOH by adding anhydrous Et2O [Bach et al. Biochemical Preparations 13 20 1971].

InChI:InChI=1/C5H9NO4.ClH/c1-10-4(7)2-3(6)5(8)9;/h3H,2,6H2,1H3,(H,8,9);1H/t3-;/m0./s1

Upstream product

• 67-56-1 methanol 
• 56-84-8 L-Aspartic acid 
• 32213-95-9 dimethyl L-aspartate hydrochloride 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 107367-92-0 (S)-2-(2-Cyclohexyl-acetylamino)-succinic acid 4-methyl ester 
• 89744-48-9 (S)-2-(Cyclohexanecarbonyl-amino)-succinic acid 4-methyl ester 
• 89744-49-0 N-(1-methylcyclohexylcarbonyl)-L-aspartic acid β-methyl ester 
• 439803-74-4 2-(4-methylbenzoylamino)butane-1,4-dioic acid 4-methyl ester 
• 145038-53-5 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acid 
• 3160-47-2 N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester 
• 76-05-1 trifluoroacetic acid 
• 155148-23-5 (S)-2-bromo-3-methoxycarbonylpropionic acid 
• 79137-59-0 N-Mesitoyl-L-asparaginsaeure-β-methylester 
• 137428-31-0 (S)-N,N-dibenzylaspartic acid β-methyl ester 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 6120-55-4 (S)-2-(2-Benzyloxycarbonylamino-acetylamino)-succinic acid 4-methyl ester 
• 89744-50-3 N-(1-methyl-3-cyclohexen-1-ylcarbonyl)-L-aspartic acid β-methyl ester 
• 107367-91-9 (S)-2-[(Cyclohex-3-enecarbonyl)-amino]-succinic acid 4-methyl ester 

Relevant articles and documents

Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis

Tris(hydrochloride) adducts of the title compounds-are prepared from the inexpensive α-amino acids H 2 N(C=O)CH 2 CH(NH 2)CO 2 H, HO(C=O)(CH 2) n ′ CH(NH 2)CO 2 H (n ′ = 1, 2), and H2 N(CH 2) 4 CH(NH 2)CO 2 H, respectively (steps/overall yield = 5/32, 7/30, 7/33, 5/38). The NH 2 group that is remote from the secondary amine is installed via BH 3 reduction of an amide [-(C=O)NR 2[ derived?-from an α-amino carboxylic acid. The MeNHCH 2 units are introduced by BH 3 reductions of alkyl carbamate [RO(C=O)NHCH 2-; R = Et, t-Bu] or amide [MeHN(C=O)-] moieties.

A method of synthesizing L - asparagine (by machine translation)

The invention provides a method of synthesizing L - asparagine, the main technical means is to L - aspartic acid as the raw material, first to the reaction in the cauldron the pump enters methanol, then open the reaction kettle, input L - aspartic acid, cooling, subsequently drop adds the chlorination sulfoxide, generating L - aspartic acid methyl ester hydrochloride, then will be of the L - aspartic acid methyl ester hydrochloride into a reaction kettle, then to the reaction in the cauldron the pump enters the ammonia, to obtain the L - asparagine, the method generating L - aspartic acid methyl ester hydrochloride intermediate product, the intermediate product is stable structure, safe and non-toxic, for subsequent operation processing, reaction process only needs to have the participation of ammonia water, reactant complex, the small influence of the product, the method of the invention recovery of the methanol up to 99.5 - 99.9%, not only improving the intermediate the purity of the product, and also avoids the pollution of methanol, L - asparagine is finished effective content of 80 - 85%, moisture content is 15 - 18%, yield and moisture content are higher than the amount of the existing products, the method of the invention is suitable for industrial production. (by machine translation)

Process for preparing deuterated desmosine and derivatives thereof

There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.

Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups

Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.

Synthesis of desmosine-containing cyclic peptide for the possible elucidation of elastin crosslinking structure

Elastin is a vital extracellular matrix protein, which is known for providing elasticity in numerous tissues. It is formed by the self-assembly and subsequent crosslinking of elastin precursor, tropoelastin. Two tetrafunctional, pyridinium-based amino acids desmosine and isodesmosine are exclusively found in elastin and play an important role as crosslinkers. Structural elucidation of elastin has eluded scientists to date, owing to the highly cross-linked structure and insoluble nature. Therefore, in this study, we aimed to synthesize a desmosine-containing cyclic peptide as a partial elastin mimic, in order to eventually facilitate the elucidation of the crosslinking pattern of elastin by mass spectrometric analysis.

Facile synthesis of urea-and thiocarbamate-tethered glycosyl beta-amino acids

We describe here an efficient way to synthesize series of new urea- and thiocarbamate-tethered glycosyl β-amino acids under mild conditions. These glycosyl β-amino acids are elaborately designed on the basis of natural N-linked glycosides. They have the same side chain length as natural N-glycosyl amino acid while the main chain is replaced with β-amino acid chain. The linkage is an isostere of natural N-linked bond but exhibits competitive stability to chemical and enzymatic hydrolysis. This facile route is benefit from the choice of the commercially available l-aspartic acid as starting material, which not only provides a β-amino acid moiety, but also the α-carboxy group could be transformed to active isocyanate conveniently and economically. The prospective glycosyl β-amino acids are obtained readily by the reaction of isocyanate with appropriately protected glycosylamines and glycosylthiols.

VERSATILE AND STEREOSPECIFIC SYNTHESIS OF GAMMA,DELTA -UNSATURATED AMINO ACIDS BY WITTIG REACTION

The present invention relates to γ,δ-unsaturated a-amino acids of general formula (I). The present invention also provides a versatile process for the stereospecific synthesis of said compounds of formula (I), involving a Wittig reaction. The present invention also relates to intermediate products of general formulae (II) and (III), as shown below, which are involved in the synthesis of compounds (I).

PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS

The present application describes general process for the preparation of amino-substitued gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substitued gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

Method of inhibiting protein tyrosine phosphatase 1B and/or T-cell protein tyrosine phosphatase 4 and/or other PTPases with an Asp residue at position 48

The present invention provides a method of inhibiting a member of a family of Protein Tyrosine Phosphatases (PTPases, PTPs) such as PTP1B, TC-PTP, CD45, SHP-1, SHP-2, PTPα, PTPε, PTPμ, PTPδ, PTPσ, PTPζ, PTPβ, PTPD1, PTPD2, PTPH1, PTP-MEG1, PTP-LAR, and HePTP by exposing said Ptpase member by administration to a host or otherwise to at least one compound with certain structural, physical and spatial characteristics that allow for the interaction of said compound with specific residues of the active site of PTP1B and/or TC-PTP. These compounds are indicated in the management or treatment of a broad range of diseases such as autoimmune diseases, acute and chronic inflammation, osteoporosis, various forms of cancer and malignant diseases, and type I diabetes and type II diabetes, as well as in the isolation of PTPases and in elucidation or further elucidation of their biological function.