2058-58-4

Basic information

• Product Name: D-(-)-Asparagine monohydrate
• Synonyms: ASPARAGINE, D-;ASPARAGINE;(D)-ASPARTIC ACID 4-AMIDE;D-ASPARAGINE;(R)-2-AMINOSUCCINIC ACID 4-AMIDE;(R)-2-Aminosuccinamic acid;H-D-Asn-OH·H2O;D-2-Aminosuccinamic acid
• CAS NO: 2058-58-4
• Molecular Formula: C₄H₈N₂O₃
• Molecular Weight: 132.12
• EINECS: 218-163-3
• Product Categories: Amino Acids Derivatives;Amino Acids and Derivatives;Amino Acids
• Mol File: 2058-58-4.mol

Chemical Properties

• Melting Point: 280 °C (dec.)(lit.)
• Boiling Point: 438 °C at 760 mmHg
• Flash Point: 218.7 °C
• Appearance: /
• Density: 1.404 g/cm³
• Vapor Pressure: 2.38E-06mmHg at 25°C
• Storage Temp.: Store at 0-5°C
• PKA: 2.17(at 20℃)
• Merck: 13,842
• BRN: 1723526
• CAS DataBase Reference: D-(-)-Asparagine monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: D-(-)-Asparagine monohydrate(2058-58-4)
• EPA Substance Registry System: D-(-)-Asparagine monohydrate(2058-58-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 2058-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-(-)-Asparagine monohydrate is used as an active pharmaceutical ingredient for the development of drugs targeting specific medical conditions. Its unique structure allows it to interact with biological systems in a way that can be beneficial for therapeutic purposes.
Used in Nutritional Supplements:
D-(-)-Asparagine monohydrate is used as a dietary supplement to support protein synthesis and overall health. Its role in the body's metabolic processes makes it a valuable addition to nutritional products aimed at enhancing athletic performance and general well-being.
Used in Research and Development:
D-(-)-Asparagine monohydrate is used as a research compound in the field of biochemistry and molecular biology. Its unique properties make it an important tool for studying the structure and function of proteins and other biomolecules, as well as for developing new drugs and therapies.
Used in Cosmetics Industry:
D-(-)-Asparagine monohydrate is used as an ingredient in the cosmetics industry, where it may be incorporated into skincare and beauty products for its potential benefits to skin health and appearance. Its role in protein synthesis could contribute to the development of anti-aging and skin repair formulations.
Used in Food Industry:
D-(-)-Asparagine monohydrate may be used in the food industry as a flavor enhancer or as a component in the production of certain food additives. Its unique properties could potentially contribute to the development of new flavors or improve the taste and texture of existing products.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 2994, 1987 DOI: 10.1248/cpb.35.2994

InChI:InChI:1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)

Upstream product

• 108-31-6 maleic anhydride 
• 3130-87-8 ASPARAGINE 
• 70-47-3 L-asparagine 
• 7664-41-7 ammonia 
• 98490-54-1 optically inactive (3,6-dioxo-piperazine-2,5-diyl)-di-acetic acid diamide 
• 7732-18-5 water 
• 21860-86-6 aspartic acid 4-ethyl ester 
• 43101-48-0 DL-aspartic acid diethyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 4474-86-6 (R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid 

Downstream Products

• 117146-35-7 N^α-[(2,4,5-trichloro-phenoxy)-acetyl]-D-asparagine 
• 1783-96-6 (2R)-aspartic acid 
• 636-61-3 D-Malic acid 
• 6293-92-1 N-(2,4-Dichlor-phenoxyacetyl)-D-asparagin 
• 617-45-8 aspartic Acid 
• 122723-93-7 N²-chloroacetyl-D-asparagine 
• 908802-63-1 2-(R)-asparagine 
• 88194-24-5 D,L-succinamopine 
• 97974-51-1 (R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-N¹-[(S)-1-((S)-1-carbamoyl-butylcarbamoyl)-2-phenyl-ethyl]-succinamide 
• 92142-18-2 N-(p-Toluolsulfonyl)-D-asparagin 
• 4474-86-6 (R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid 
• 7536-55-2 N-t-butyloxycarbonyl-D-asparagine 
• 727740-59-2 (2R,4R)-3-benzoyl-1,2,3,4,5,6-hexahydro-2-(1-methylethyl)-6-oxopyrimidine-4-carboxylic acid 
• 859235-81-7 MeZ-(R)-Asn-OH 

Relevant articles and documents

Pasteur-like resolution of quasi-racemates in solid and gas phases

Isotopomeric quasi-racemates (IQR), i.e., 1:1 mixtures of enantiomers one of which contains an isotopic label, can undergo crystallisation as conglomerates or true quasi-racemates. In the former case, each single crystal contains, predominantly or exclusi

β-Cyclodextrin Functionalized Nanoporous Graphene Oxides for Efficient Resolution of Asparagine Enantiomers

Efficient resolution of racemic mixture has long been an attractive but challenging subject since Pasteur separated tartrate enantiomers in 19th century. Graphene oxide (GO) could be flexibly functionalized by using a variety of chiral host molecules and therefore, was expected to show excellent enantioselective resolution performance. However, this combination with efficient enantioselective resolution capability has been scarcely demonstrated. Here, nanoporous graphene oxides were produced and then covalently functionalized by using a chiral host material-β-cyclodextrin (β-CD). This chiral GO displayed enantioselective affinity toward the l-enantiomers of amino acids. In particular, >99 % of l-asparagine (Asn) was captured in a racemic solution of Asn while the adsorption of d-enantiomer was not observed. This remarkable resolution performance was subsequently modelled by using an attach-pull-release dynamic method. We expect this preliminary concept could be expanded to other chiral host molecules and be employed to current membrane separation technologies and finally show practical use for many other racemates.

Noncovalently Functionalized Commodity Polymers as Tailor-Made Additives for Stereoselective Crystallization

Stereoselective inhibition of the nucleation and crystal growth of one enantiomer aided by “tailor-made” polymeric additives is an efficient method to obtain enantiopure compounds. However, the conventional preparation of polymeric additives from chiral monomers are laborious and limited in structures, which impedes their rapid optimization and applicability. Herein, we report a “plug-and-play” strategy to facilitate synthesis by using commercially available achiral polymers as the platform to attach various chiral small molecules as the recognition side-chains through non-covalent interactions. A library of supramolecular polymers made up of two vinyl polymers and six small molecules were applied with seeds in the selective crystallization of seven racemates in different solvents. They showed good to excellent stereoselectivity in yielding crystals with high enantiomeric purities in conglomerates and racemic compound forming systems. This convenient, low-cost modular synthesis strategy of polymeric additives will allow for high-efficient, economical resolution of various racemates on different scales.

Self-Reporting Inhibitors: A Single Crystallization Process To Obtain Two Optically Pure Enantiomers

Collection of two optically pure enantiomers in a single crystallization process can significantly increase the chiral separation efficiency but this is difficult to realize. Now a self-reporting strategy is presented for visualizing the crystallization process by a dyed self-assembled inhibitor made from the copolymers with tri(ethylene glycol)-grafting polymethylsiloxane as the main chain and poly(N6-methacryloyl-l-lysine) as side chains. When applied with seeds together for the fractional crystallization of conglomerates, the inhibitors can label the formation of the secondary crystals and guide the complete separation process of two enantiomers with colorless crystals as the first product and red crystals as the second. This method leads to high optical purity of d/l-Asn?H2O (99.9 % ee for d-crystals and 99.5 % for l-crystals) in a single crystallization process. It requires a small amount of additives and shows excellent recyclability.

Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC

Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3'-halogen substituted-1,1'-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one α-amino acids have different degrees of separation on R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1'-binaphthyl)-20-crown-6 derivatives. Both the separation factors (α) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 chiral stationary phase.

SEPARATING AGENT AND MANUFACTURING METHOD THEREOF

An embodiment of the present invention is a separating agent wherein a group represented by a chemical formula of: or a group represented by a chemical formula of: is introduced on a surface thereof.

SEPARATING AGENT FOR CHROMATOGRAPHY

A separating agent for chromatography is provided that is useful for the separation of specific compounds, e.g., for the optical resolution of amino acids. This separating agent for chromatography provides a higher productivity and contains a crown ether-like cyclic structure and optically active binaphthyl. This separating agent for chromatography containing a crown ether-like cyclic structure and optically active binaphthyl is provided by introducing a substitution group for binding to carrier into a specific commercially available 1,1′-binaphthyl derivative that has substituents at the 2, 2′, 3, and 3′ positions, then introducing a crown ether-like cyclic structure, and subsequently chemically bonding the binaphthyl derivative to the carrier through the substitution group for binding to carrier.

Preparation of D-amino acids by enzymatic kinetic resolution using a mutant of penicillin-G acylase from E. coli

We have demonstrated for the first time that d-glutamine (d-Gln) and d-glutamic acid (d-Glu) can be efficiently obtained in high ee (97% and 90%, respectively) by enzymatic kinetic resolution of d,l-Gln and d,l-Glu. This was achieved by enantioselective conversion of the l-enantiomers to their N-phenylacetyl derivatives in aqueous solution, using a mutant of penicillin-G acylase (PGA) from E. coli and phenylacetic acid methylester as the acyl donor. Kinetic modeling studies suggest that the high ee values obtained are both due to a strong enantiopreference for the l-amino acid in the deacylation step of the covalent enzyme intermediate, as well as to completeness of conversion that is transiently obtained as a result of the distinct preference of the mutant PGA for phenylacetic acid methylester over the N-phenylacetyl-l-amino acid product. For the other amino acids tested (Asn, Asp, and Ser), the highest ee values that were obtained for the remaining d-enantiomer are moderate (50-80%) because of lower enantioselectivity in the enzyme deacylation step and due to less complete conversion of the l-amino acid caused by competition for the active site between the acyl donor and the N-phenylacetyl-l-amino acid that is produced. The results demonstrate that the mutated PGA has great potential for the production of optically active D-amino acids by kinetic resolution.

Resolution of DL-racemic mixtures

The present invention relates to a process for the resolution of DL-racemic mixtures of compounds which crystalize in the form of a conglumerate. Both, the D and L-enantiomers are obtained according to the invention in a industrially feasable process by adding chiral enantioselective polymers to the supersaturated solution of the racemat to inhibit crystalization of one enantiomer. Next a DL-racemic mixture of said compound is suspended in about twice the amount of the crystallized enantiomer. Consequently, the opposite enantiomer could be recovered by said suspension by physical separation.

Retention and selectivity of teicoplanin stationary phases after copper complexation and isotopic exchange

Teicoplanin is a macrocyclic glycopeptide that is highly effective as a chiral selector for LC enantiomeric separations. Two possible interaction paths were investigated and related to solute retention and selectivity: (1) interactions with the only teicoplanin amine group and (2) role of hydrogen bonding interactions. Mobile phases containing 0.5 and 5 mM copper ions were used to try to block the amine group. In the presence of copper ions, it was found that the teicoplanin stationary phase has a decreased ability to separate most underivatized racemic amino acids. However, it maintained its ability to separate enantiomers that were not α - amino acids. It is established that there is little copper - teicoplanin complex formation. The effect of Cu2+ on the enantioseparation of some α - amino acids appears to be due to the fact that these solutes are good bidentate ligands and form complexes with copper ions in the mobile phase. Isotopic exchange with deuterium oxide was performed using acetonitrile - heavy water mobile phases. It was found that the retention times of all amino acids were lower with deuterated mobile phases. The retention times of polar or apolar molecules without amine groups were higher with deuterated mobiles phases. In all cases, the enantio-selectivity factors were unaffected by the deuterium exchange. It is proposed that the electrostatic interactions are decreased in the deuterated mobile phases and the solute-accessible stationary-phase volume is somewhat swollen by deuterium oxide. The balance of these effects is a decrease in the amino acid retention times and an increase in the apolar solute retention time. The enantio-selectivity factors of all of the molecules remain unchanged because all of the interactions are changed equally. We propose a new global quality criterion (the E factor) for comparing and evaluating enantiomeric separations.