D-Glutamine, with the CAS number 5959-95-5, is the D-enantiomer of L-glutamine, an important chiral amino acid, also known as D-2-Aminoglutamic acid amide. Its molecular formula is C₅H₁₀N₂O₃, and its molecular weight is 146.14 g/mol. As a non-proteinogenic amino acid (not incorporated into natural proteins), it possesses unique chiral properties, good stability, and specific biochemical activities, making it widely applied in biochemistry research, pharmaceutical synthesis, chiral catalysis, and food additive fields.
Physically, D-Glutamine appears as a white to off-white crystalline powder or granular solid. It has a melting point of approximately 185-189℃ (decomposition) and is highly soluble in water, forming a clear and stable aqueous solution, while it is slightly soluble in methanol and ethanol, and insoluble in non-polar solvents. It is optically active, with a specific rotation [α]²⁰/D of +6.5° to +10.5° (in water, c=2). It has low hygroscopicity and remains stable under normal temperature and pressure when stored properly, facilitating easy handling, storage, and formulation.
Chemically, it contains an amino group, a carboxyl group, and an amide group—the key functional groups determining its properties. Unlike L-glutamine (the naturally occurring enantiomer), D-Glutamine does not participate in protein synthesis in organisms but exhibits unique chiral reactivity. It is stable under neutral and weakly acidic conditions but may hydrolyze under strong acid, strong alkali, or high-temperature environments, decomposing into D-glutamic acid. Its chiral structure makes it an ideal chiral building block for organic synthesis and pharmaceutical research.
Its core applications focus on biochemistry, pharmaceuticals, and chiral synthesis. In biochemistry research, it is used as a biochemical reagent for studying enantiomer-specific reactions, amino acid metabolism, and chiral recognition, serving as a reference standard for distinguishing D- and L-enantiomers. In the pharmaceutical industry, it acts as a key chiral intermediate for synthesizing peptide drugs, antiviral agents, and chiral pharmaceuticals, especially for drugs requiring specific enantiomeric purity.
In chiral catalysis, it is used as a chiral ligand to promote asymmetric reactions, improving the efficiency and enantioselectivity of organic synthesis. Additionally, it is used as a food additive and nutritional supplement in specific scenarios. Safety-wise, it is generally recognized as safe (GRAS), non-toxic and non-irritating under normal handling. It should be stored in a sealed, cool, dry, and dark environment at 2-8℃, away from strong oxidants, moisture, and high temperatures to prevent hydrolysis and degradation. With its unique chiral properties and versatile applications, it is an indispensable raw material in chiral chemistry and pharmaceutical research.
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