D-Asparagine hydrate
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D-Asparagine hydrate

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Category
D-Amino Acids
Catalog number
BAT-003478
CAS number
2058-58-4
Molecular Formula
C4H8N2O3·H2O
Molecular Weight
150.10
D-Asparagine hydrate
IUPAC Name
(2R)-2,4-diamino-4-oxobutanoic acid
Synonyms
D-Asn-OH H2O; (R)-2-Aminosuccinic acid 4-amide monohydrateD-2-Aminobutanedioic acid monohydrate; (2R)-2-amino-3-carbamoylpropanoic acid
Appearance
White to off-white powder
Purity
≥ 98.5% (Titration)
Density
1.404±0.06 g/cm3(Predicted)
Melting Point
280 °C (dec.)(lit.)
Boiling Point
438.0±40.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1
InChI Key
DCXYFEDJOCDNAF-UWTATZPHSA-N
Canonical SMILES
C(C(C(=O)O)N)C(=O)N

D-Asparagine hydrate is a crystalline form of the amino acid D-asparagine, combined with water molecules. D-asparagine is an enantiomer of L-asparagine, meaning it has a mirror-image structure. This compound plays a vital role in various biological processes, such as nitrogen metabolism and the synthesis of proteins. The hydrate form enhances the stability and solubility of D-asparagine, making it more practical for industrial applications. Its unique stereochemistry allows it to participate in specialized reactions that are critical in biochemical and pharmaceutical industries.

One of the key industrial applications of D-asparagine hydrate is in the pharmaceutical sector, where it is utilized in the development of enantiomerically pure drugs. Many drugs require specific enantiomers to be effective or reduce unwanted side effects. D-asparagine hydrate serves as a chiral building block, aiding in the synthesis of these enantiomerically pure compounds. Its role is particularly important in the production of antiviral and anticancer drugs, where precision in molecular configuration is critical.

Another important use of D-asparagine hydrate is in biotechnology, specifically in protein engineering and enzyme synthesis. The compound can be incorporated into peptide chains or serve as a precursor for enzymes. This helps in creating novel proteins with desired properties, such as increased stability or altered substrate specificity. D-asparagine hydrate is especially useful in the development of industrial enzymes that are employed in large-scale biocatalysis processes.

In the food and beverage industry, D-asparagine hydrate is employed as an additive to enhance flavor profiles, particularly in the production of sweeteners and flavor enhancers. Its role in the Maillard reaction, a chemical reaction between amino acids and reducing sugars, helps in creating the complex flavors associated with baked and roasted foods. This makes it a valuable ingredient in processed foods, contributing to both taste and aroma.

D-Asparagine hydrate is also important in the agricultural industry, where it is used in the formulation of bioactive agents, such as plant growth regulators. These agents can improve crop yield and stress tolerance, promoting healthier plant development. By acting as a precursor for bioactive compounds, D-asparagine hydrate supports sustainable agricultural practices and enhances the efficiency of crop production.

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