2-Aminoisobutyric acid - 62-57-7

2-Aminoisobutyric acid

Catalog Number: EVT-249034
CAS Number: 62-57-7
Molecular Formula: C4H9NO2
Molecular Weight: 103,12 g/mole
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
2-Aminoisobutyric acid (AIB) is a non-proteinogenic amino acid that is widely distributed in nature. It is also known as alpha-aminoisobutyric acid or 2-methylalanine. AIB is an important building block for the synthesis of various peptides and proteins. It has been found to possess several biological activities, including antimicrobial, antitumor, and antiviral properties.
Applications in Various Fields
AIB has several applications in medical research, environmental research, and industrial research. In medical research, AIB has been studied for its role in drug development. AIB has been found to have antitumor and antiviral properties, which make it a promising candidate for the development of new drugs. AIB has also been studied in clinical trials for its potential therapeutic effects. In environmental research, AIB has been studied for its effects on ecosystems and its role in pollution management. AIB has been found to have a low environmental impact and can be used as a sustainable alternative to toxic chemicals. In industrial research, AIB has been used in manufacturing processes to improve product quality and efficiency. AIB has also been used to enhance the health and safety of workers in industrial settings.

Properties

CAS Number

62-57-7

Product Name

2-Aminoisobutyric acid

IUPAC Name

2-amino-2-methylpropanoic acid

Molecular Formula

C4H9NO2

Molecular Weight

103,12 g/mole

InChI

InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)

InChI Key

FUOOLUPWFVMBKG-UHFFFAOYSA-N

SMILES

CC(C)(C(=O)O)N

Solubility

1.76 M
181 mg/mL at 25 °C

Synonyms

2-aminoisobutyric acid
2-aminoisobutyric acid, 11C-labeled
2-aminoisobutyric acid, 14C-labeled
2-methylalanine
alpha-aminoisobutyrate
alpha-aminoisobutyric acid
alpha-methylalanine

Canonical SMILES

CC(C)(C(=O)[O-])[NH3+]
Method of Synthesis or Extraction
AIB can be synthesized by several methods, including the Strecker synthesis, the Gabriel synthesis, and the reductive amination of pyruvate. The Strecker synthesis involves the reaction of an aldehyde or ketone with ammonia and hydrogen cyanide. The Gabriel synthesis involves the reaction of phthalimide with potassium hydroxide and diethyl sulfate, followed by hydrolysis and decarboxylation. The reductive amination of pyruvate involves the reaction of pyruvate with ammonia and sodium borohydride. The efficiency and yield of each method vary depending on the starting materials and reaction conditions. The Strecker synthesis is the most commonly used method for the synthesis of AIB. However, it involves the use of toxic and hazardous chemicals, such as hydrogen cyanide, which poses environmental and safety considerations.
Chemical Structure and Biological Activity
AIB has a unique chemical structure, with a methyl group attached to the alpha-carbon of the amino acid. This structural feature makes AIB resistant to proteolysis and enhances its bioactivity. AIB has been found to possess several biological activities, including antimicrobial, antitumor, and antiviral properties. AIB acts as a competitive inhibitor of alanine aminotransferase, which is involved in the metabolism of amino acids. AIB also inhibits the growth of several cancer cell lines by inducing apoptosis and cell cycle arrest. AIB has been shown to inhibit the replication of several viruses, including HIV-1, by interfering with viral entry and fusion.
Biological Effects
AIB has been found to have several biological effects on cell function and signal transduction. AIB has been shown to modulate the activity of several enzymes, including alanine aminotransferase, glutamate dehydrogenase, and pyruvate kinase. AIB also regulates the expression of several genes involved in cell growth, differentiation, and apoptosis. AIB has been found to have potential therapeutic and toxic effects. AIB has been shown to have antitumor and antiviral properties, which make it a promising candidate for drug development. However, AIB has also been found to have toxic effects on the liver and kidneys, which limit its clinical use.
Future Perspectives and Challenges
The use and study of AIB face several limitations and challenges. The synthesis of AIB involves the use of toxic and hazardous chemicals, which poses environmental and safety considerations. The clinical use of AIB is limited by its toxic effects on the liver and kidneys. The future perspectives of AIB lie in the development of new methods for its synthesis and the discovery of new applications for its use. Possible solutions and improvements include the use of green chemistry methods for the synthesis of AIB and the development of new drug delivery systems to enhance its therapeutic effects. The future trends and prospects in the application of AIB in scientific research are promising, and further studies are needed to fully understand its potential.
Conclusion:
In conclusion, AIB is a non-proteinogenic amino acid that possesses several biological activities, including antimicrobial, antitumor, and antiviral properties. AIB has several applications in medical research, environmental research, and industrial research. The use and study of AIB face several limitations and challenges, but the future perspectives and prospects are promising. Further studies are needed to fully understand the potential of AIB in scientific research.

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