608528-91-2

Usage

Uses

Used in Pharmaceutical Research:
(S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID is used as a key building block in the synthesis of peptidomimetics and peptidic drug molecules, contributing to the development of innovative therapeutic agents with improved pharmacological properties.
Used in Organic Synthesis:
As a chiral compound with an asymmetric carbon center, (S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID is utilized in the synthesis of enantiomerically pure compounds, which are essential for various applications in the chemical and pharmaceutical industries.
Used in Drug Development:
(S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID serves as a valuable component in the development of novel drug candidates, providing a structural foundation for the creation of new therapeutic agents with potential applications in various medical fields.
Used in Molecular Interaction Studies:
(S)-3-BIPHENYL-3-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID is employed in the study of molecular interactions involving amino acid derivatives, helping researchers understand their effects on biological systems and contributing to the advancement of our knowledge in the field of medicinal chemistry.

Upstream product

• 273221-75-3 (S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodophenyl)propanoic acid 
• 1287221-44-6 benzyl (S)-3-([1,1’-biphenyl]-3-yl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 14473-91-7 3-bromocinnamic acid 
• 82278-73-7 (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Intensified biocatalytic production of enantiomerically pure halophenylalanines from acrylic acids using ammonium carbamate as the ammonia source

An intensified, industrially-relevant strategy for the production of enantiopure halophenylalanines has been developed using the novel combination of a cyanobacterial phenylalanine ammonia lyase (PAL) and ammonium carbamate reaction buffer. The process boasts STYs up to >200 g L-1 d-1, ees ≥ 98% and simplified catalyst/reaction buffer preparation and work up.

LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs

The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has been found to be up-regulated in many different tumor types, and its expression levels have been correlated with prognosis. Substitution at the meta position of aromatic amino acids has been reported to increase affinity for LAT-1; however, the SAR for this position has not previously been explored. Guided by newly refined computational models of the binding site, we hypothesized that groups capable of filling a hydrophobic pocket would increase binding to LAT-1, resulting in improved substrates relative to parent amino acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted phenylalanine and tyrosine analogs is described.