Phenylalanine is an essential amino acid that plays a vital role in the synthesis of proteins. There are two forms of phenylalanine: L-phenylalanine and D-phenylalanine. However, researchers have recently discovered a third form of this amino acid, which is known as L-4/'>4-tert-Butylphenylalanine or L-tBPA. L-tBPA has a similar structure to L-phenylalanine but has a tert-butyl group attached to it that enhances its activity. In this blog, we will discuss L-tBPA's properties and its applications, along with its CAS number 3/'>388077-74-5.
Properties of L-4-tert-Butylphenylalanine:
CAS Number: 388077-74-5
Molecular Formula: C15H21NO2
Molecular Weight: 247.33 g/mol
Appearance: White powder
Melting Point: 138-140°C
Solubility: Soluble in water
Synthesis of L-4-tert-Butylphenylalanine:
There are different methods to synthesize L-tBPA. One of the most common methods is the asymmetric hydrogenation of ketone precursor 4-tert-butylcinnamic acid using a chiral catalyst. Another method is the direct N-alkylation of L-phenylalanine using tert-butyl bromoacetate.
Applications of L-4-tert-Butylphenylalanine:
L-tBPA has several applications in the field of pharmaceuticals and biotechnology.
1. As a chiral auxiliary:
L-tBPA can be used as a chiral auxiliary in the asymmetric synthesis of drugs and biologically active molecules. It helps to produce enantiomerically pure compounds, which have better pharmacological properties and reduced side effects.
2. As a ligand:
L-tBPA can act as a ligand for metal ions like copper, palladium, and platinum. The resulting complexes have shown promising applications in catalysis, organic synthesis, and medicinal chemistry.
3. As a building block:
L-tBPA can be used as a building block in the synthesis of peptides and proteins. Its tert-butyl group helps to enhance its stability and makes it resistant to hydrolysis.
4. As a drug:
L-tBPA derivatives have shown potential as anti-inflammatory and anti-cancer agents. For example, N-[(4-tert-butylphenyl) carbamoyl]-L-glutamic acid (BPTES) is a potent inhibitor of glutaminase, which is overexpressed in many cancer cells.
Conclusion:
L-4-tert-Butylphenylalanine or L-tBPA is a unique amino acid that has several applications in the field of pharmaceuticals and biotechnology. Its tert-butyl group enhances its activity and stability, making it an attractive building block for drug development. The CAS number of L-tBPA is 388077-74-5. As research in this field progresses, we can expect to see new and exciting applications of L-tBPA in the future.