Acetyl-L-alanine amide
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Acetyl-L-alanine amide

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Category
L-Amino Acids
Catalog number
BAT-003904
CAS number
15962-47-7
Molecular Formula
C5H10N2O2
Molecular Weight
130.10
Acetyl-L-alanine amide
IUPAC Name
(2S)-2-acetamidopropanamide
Synonyms
Ac-L-Ala-NH2; (S)-2-Acetamidopropanamide
Appearance
White to off-white powder
Purity
≥ 99% (TLC)
Density
1.2268 g/cm3(rough estimate)
Melting Point
160-164 °C
Boiling Point
240.83°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C5H10N2O2/c1-3(5(6)9)7-4(2)8/h3H,1-2H3,(H2,6,9)(H,7,8)/t3-/m0/s1
InChI Key
DVOVBGJJSFSOPZ-VKHMYHEASA-N
Canonical SMILES
CC(C(=O)N)NC(=O)C

Acetyl-L-alanine amide, a derivative of the amino acid alanine, finds its application in the field of pharmaceuticals and drug design. Its unique molecular structure makes it a valuable component in the development of peptide-based drugs. The acetyl group enhances the molecule's stability and bioavailability, making it more effective in targeted drug delivery systems. Researchers are particularly interested in its potential to improve the efficacy and safety profile of peptide therapeutics, which can be used to treat a variety of conditions, including metabolic disorders, autoimmune diseases, and cancer. The versatility of Acetyl-L-alanine amide in forming stable peptide bonds also aids in the synthesis of complex pharmaceuticals.

In the realm of biochemistry and molecular biology, Acetyl-L-alanine amide serves as a crucial tool in protein research and peptide synthesis. It is often used in the study of enzyme kinetics and protein-protein interactions due to its ability to mimic peptide bonds within protein structures. This makes it an excellent candidate for probing the active sites of enzymes and understanding the mechanisms of catalysis and inhibition. Additionally, its use in peptide sequencing and structure determination experiments helps in elucidating the functional and conformational aspects of proteins, thereby advancing our knowledge of cellular processes and molecular function.

The cosmetic industry also capitalizes on the benefits of Acetyl-L-alanine amide, leveraging its properties to develop anti-aging and skin care products. It is commonly included in formulations to enhance skin hydration and elasticity, combat oxidative stress, and promote collagen synthesis. Due to its ability to penetrate skin barriers efficiently, it aids in the delivery of active ingredients to deeper layers of the skin, thereby improving the efficacy of cosmetic products. Companies are increasingly incorporating Acetyl-L-alanine amide in serums, creams, and lotions aimed at reducing fine lines, wrinkles, and other signs of aging.

In the field of food science and nutrition, Acetyl-L-alanine amide is utilized as a functional additive and flavor enhancer. Its presence in food products can improve taste profiles, enhance nutritional value, and contribute to overall product stability and shelf life. It is particularly valuable in the formulation of dietary supplements and functional foods designed to support metabolic health and physical performance. By aiding in the delivery of essential amino acids and peptides, Acetyl-L-alanine amide helps in the maintenance of health and wellbeing. It also finds use in sports nutrition products where it supports muscle recovery and endurance. This multifaceted utility makes it a popular choice among food scientists and product developers aiming to create healthier, more effective food solutions.

1.The alanine model dipeptide Ac-Ala-NH2 exists as a mixture of C7(eq) and C5 conformers.
Cabezas C1, Varela M, Cortijo V, Jiménez AI, Peña I, Daly AM, López JC, Cativiela C, Alonso JL. Phys Chem Chem Phys. 2013 Feb 21;15(7):2580-5. doi: 10.1039/c2cp43924g. Epub 2013 Jan 14.
Microwave spectroscopy has been applied to characterize the conformations adopted in the gas phase by a small peptide derived from alanine, N-acetyl-L-alaninamide (Ac-Ala-NH(2)). This compound was vaporized by laser ablation and shown to exist as a mixture of C(eq)(7) and C(5) conformers stabilized by a CO···HN intramolecular hydrogen bond closing a seven- or a five-membered ring, respectively. The complicated quadrupole hyperfine structure originated from two (14)N nuclei has been completely resolved for both species and the derived nuclear quadrupole coupling constants have been used to determine the Ramachandran angles that describe their molecular shapes.
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