L-Alanine
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L-Alanine

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L-alanine is a non-essential amino acid involved in the metabolism of tryptophan and vitamin pyridoxine.

Category
L-Amino Acids
Catalog number
BAT-014294
CAS number
56-41-7
Molecular Formula
C3H7NO2
Molecular Weight
89.09
L-Alanine
IUPAC Name
(2S)-2-aminopropanoic acid
Synonyms
Alanine; (S)-Alanine; H-Ala-OH; Alanine, L-; (2S)-2-Azaniumylpropanoate; (S)-(+)-Alanine; (S)-2-Aminopropanoic acid; L-(+)-Alanine; L-2-Aminopropanoic acid; L-2-Aminopropionic acid; L-α-Alanine; L-α-Aminopropionic acid; Lactamine; NSC 206315; Propanoic acid, 2-amino-, (S)-; α-Alanine; α-Aminopropionic acid
Related CAS
6898-94-8 (Deleted CAS) 115967-49-2 (Deleted CAS) 170805-71-7 (Deleted CAS) 759445-89-1 (Deleted CAS) 787635-21-6 (Deleted CAS) 1150316-17-8 (Deleted CAS)
Appearance
White Crystals or Crystalline Powder
Purity
>98%
Density
1.432 g/cm3
Melting Point
300°C (dec.)
Boiling Point
212.9±23.0°C at 760 mmHg
Storage
Store at -20°C
Solubility
Soluble in Aqueous Acid (Slightly), Water (Slightly), Aqueous Base (Slightly)
InChI
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
InChI Key
QNAYBMKLOCPYGJ-REOHCLBHSA-N
Canonical SMILES
CC(C(=O)O)N

L-Alanine is a non-essential amino acid that plays a vital role in various biological processes in the human body. It is classified as an alpha-amino acid, which means that it contains an amino group and a carboxylic acid group located on the alpha carbon atom. As one of the building blocks of protein, L-Alanine is involved in a variety of metabolic pathways and functions that are essential to overall health. L-Alanine has a variety of applications in fields such as sports nutrition, medicine, and the food industry:

1. Sports Nutrition: Because it affects muscular function and energy metabolism, l-alanine is crucial in the field of sports nutrition. The body uses more energy during periods of prolonged, vigorous exercise, which leads to the breakdown of muscle protein for fuel. L-alanine supplements can assist avert muscle breakdown by offering a substitute energy source. Furthermore, L-alanine is believed to aid in the gluconeogenesis process, which produces glucose and improves physical strength and endurance. L-alanine pills are frequently used by athletes and fitness enthusiasts to promote muscle repair, enhance performance, and sustain peak energy levels throughout exercise.

2. Medicine: Because of its medicinal qualities, L-alanine has several useful applications in the medical field. L-alanine plays a significant role in the management of hypoglycemia, a disorder marked by low blood sugar. L-alanine helps raise blood sugar levels and reduce hypoglycemic episodes in people with diabetes or other similar illnesses since it is a precursor to the creation of glucose. Additionally, patients who are malnourished, have had serious burns, or are having surgery can benefit from intravenous (IV) solutions containing L-alanine, which provides necessary amino acids and supports protein synthesis.

Furthermore, L-alanine is essential for liver function and detoxification procedures. L-alanine strengthens the body's antioxidant defenses and aids in the neutralization of dangerous free radicals that can destroy cells and tissues. It is a constituent of the tripeptide glutathione. L-alanine enhances detoxification processes and supports liver function, which improves general health and helps fend off disorders linked to oxidative stress.

3. Food Industry: In the food industry, L-alanine plays a variety of roles in food production and processing. This amino acid is often used as a flavor enhancer and food additive to improve the taste and palatability of processed foods and beverages. L-alanine contributes to the overall umami flavor, known for enhancing the salty taste of foods such as soups, sauces, and snacks. In addition, L-alanine can be used as a stabilizer and texturizer in foods to extend their shelf life, improve texture, and maintain quality during storage and transportation.

In addition, L-alanine plays a vital role in food preservation and fermentation processes. As a precursor for the synthesis of nitrogen-containing compounds, L-alanine helps promote the growth of beneficial microorganisms in fermented foods such as yogurt, cheese, and kimchi. By supporting microbial growth and metabolic activities, L-alanine contributes to the formation of unique flavors, textures, and aromas in fermented foods.

4. Biotechnology and pharmaceutical research: In the field of biotechnology and pharmaceutical research, L-alanine can be used to produce recombinant proteins, antibodies, and other biopharmaceuticals. Due to its stability and compatibility with various expression systems, L-alanine is often used as a fusion tag or linker in protein engineering and purification processes. By attaching L-alanine residues to target proteins, researchers can facilitate protein expression, purification, and characterization to develop new biologics and therapeutics.

In addition, due to its chemical properties and biocompatibility, L-alanine is used to synthesize peptide drugs and pharmaceutical preparations. Peptides containing L-alanine residues exhibit improved stability, solubility, and bioavailability, making them promising candidates for drug delivery mechanisms and disease treatment modalities. In addition, L-alanine derivatives and analogs are being investigated for potential pharmacological activities and therapeutic applications in areas such as cancer therapy, antimicrobial resistance, and metabolic disorders.

1.Metabolic engineering of microorganisms for L-alanine production
J Ind Microbiol Biotechnol. 2022 Apr 14;49(2):kuab057. doi: 10.1093/jimb/kuab057.
L-alanine is extensively used in chemical, food, and medicine industries. Industrial production of L-alanine has been mainly based on the enzymatic process using petroleum-based L-aspartic acid as the substrate. L-alanine production from renewable biomass using microbial fermentation process is an alternative route. Many microorganisms can naturally produce L-alanine using aminotransferase or L-alanine dehydrogenase. However, production of L-alanine using the native strains has been limited due to their low yields and productivities. In this review, metabolic engineering of microorganisms for L-alanine production was summarized. Among them, the Escherichia coli strains developed by Dr. Lonnie Ingram's group which can produce L-alanine with anaerobic fermentation process had several advantages, especially having high L-alanine yield, and it was the first one that realized commercialization. L-alanine is also the first amino acid that could be industrially produced by anaerobic fermentation.
2.[Alanine aminotransferase (ALT)]
Nihon Rinsho. 1995 May;53(5):1146-50.
Alanine aminotransferase (Alt, L-alanine:2-oxoglutalate aminotransferase) is a pyridoxal enzyme which catalyses the reversible interconversion of L-alanine and 2-oxoglutalate to pyruvate and L-glutamate. The enzyme is widely distributed in various tissues from animals and even in some kind of plants. Isoenzymes of human ALT localize in the cytosol (c-ALT) and mitochondria (m-ALT) of tissues such as liver, kidney, skeletal and cardiac muscles. Amino acid sequence of c-ALT from rat and human liver has been wholly determined by Ishiguro et al. It is suggested that c-ALT is associated to the utilization of pyruvate in glycolysis and m-ALT is involved in the conversion of alanine to pyruvate for gluconeogenesis.
3.Biomedical applications of L-alanine produced by Pediococcus acidilactici BD16 (alaD+)
Appl Microbiol Biotechnol. 2022 Feb;106(4):1435-1446. doi: 10.1007/s00253-022-11766-9.
L-alanine possesses extensive physiological functionality and tremendous pharmacological significance, therefore could be considered as potential ingredient for food, pharmaceutical, and personal care products. However, therapeutic properties of L-alanine still need to be addressed in detail to further strengthen its utilization as a viable ingredient for developing natural therapeutics with minimum side effects. Thus, the present study was aimed to explore the anticipated therapeutic potential of L-alanine, produced microbially using a lactic acid bacterial strain Pediococcus acidilactici BD16 (alaD + ) expressing L-alanine dehydrogenase enzyme. The anticipated therapeutic potential of L-alanine was assessed in terms of anti-proliferative, anti-bacterial, and anti-urolithiatic properties. Anti-bacterial assays revealed that L-alanine successfully inhibited growth and in vitro proliferation of important human pathogens including Enterococcus faecalis, Escherichia coli, Klebsiella pneumonia, Staphylococcus aureus, Streptococcus mutans, and Vibrio cholerae in a concentration-dependent manner. Current investigation has also revealed its significant anti-proliferative potential against human lung adenocarcinoma (A549; IC 50 7.32 μM) and mammary gland adenocarcinoma (MCF-7; IC 50 8.81 μM) cells. The anti-urolithiatic potential of L-alanine was augmented over three different phases, viz., nucleation inhibition, aggregation inhibition, and oxalate depletion. Further, an in vitro cell culture-based kidney stone dissolution model using HEK293-T cells was also established to further strengthen its anti-urolithiatic potential. This is probably the first in vitro cell culture-based model which experimentally validates the immense therapeutic efficacy of L-alanine in treating urolithiasis disease. KEY POINTS: • Assessment of therapeutic potential of L-alanine produced by LAB. • L-alanine exhibited significant anti-proliferative and anti-bacterial activities. • L-alanine as potential anti-urolithiatic agent.
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