L-Prolinamide
[CAS# 7531-52-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other protected amino acids
• Name: L-Prolinamide
• Molecular Formula: C₅H₁₀N₂O
• Molecular Weight: 114.15
• Protein Sequence: P
• CAS Registry Number: 7531-52-4
• EC Number: 231-397-0
• SMILES: C1C[C@H](NC1)C(=O)N

Properties

• Melting point: 97-102 °C
• alpha: -106 ° (c=2, EtOH)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

L-Prolinamide is a derivative of the amino acid proline with the chemical name (2S)-2-pyrrolidineamide, derived from the amino acid L-proline. Its synthesis involves the amidation of L-proline, where the carboxyl group (-COOH) of L-proline is converted to an amide group (-CONH₂). This conversion results in the formation of L-prolinamide, a compound that retains the unique structural features of proline, including its pyrrolidine ring and amide functionality.

L-Prolinamide is typically a white to off-white crystalline solid that is soluble in water and polar organic solvents. The melting point is about 115-118°C.

L-Prolinamide exhibits pharmaceutical relevance in several areas: It is used as a chiral auxiliary in asymmetric synthesis, especially in the preparation of enantiomerically pure compounds. By exploiting the chiral properties of L-prolinamide, chemists can control the stereochemistry of reactions, thereby improving the efficiency and selectivity of organic synthesis processes. L-Prolinamide derivatives act as efficient organocatalysts in various organic reactions, such as aldol reactions and Michael addition reactions. These catalytic properties make it possible to synthesize complex molecules with high stereoselectivity under mild reaction conditions.

L-prolineamide and its derivatives have been studied for their biological activities, including interactions with enzymes and receptors. These studies have helped to understand biochemical processes and develop therapeutics targeting specific biological pathways. Research has also explored the therapeutic potential of L-prolineamide in areas such as neurology, where its interactions with neurotransmitter receptors and the nervous system have been studied for potential drug development.

L-prolineamide is used as a monomer or polymer additive in polymer chemistry. Its incorporation can modify the physical and chemical properties of polymers, enhancing their mechanical strength, thermal stability, and biocompatibility.

Standard laboratory safety procedures should be followed when handling L-prolineamide. This includes wearing appropriate personal protective equipment (PPE) and working in well-ventilated areas to minimize exposure risks.

Ongoing research focuses on expanding synthetic methods involving L-prolineamide derivatives and exploring new applications in medicinal chemistry, materials science, and biological research. Advances in the understanding of its molecular interactions and the development of novel derivatives may lead to enhanced therapeutics and functional materials.

References

none