155760-02-4

Basic information

• Product Name: L-4,4'-BIPHENYLALANINE
• Synonyms: (S)-4-BIPHENYL-ALANINE;(S)-4-BIPHENYLYL-ALANINE;(S)-2-AMINO-3-BIPHENYL-4-YL-PROPIONIC ACID;(S)-2-AMINO-3-(1,1'-BIPHENY-4-YL)PROPANOIC ACID;H-4-PHENYL-L-PHE-OH;H-4-PHENYL-PHE-OH;H-BIP(4,4')-OH;H-BIP-OH
• CAS NO: 155760-02-4
• Molecular Formula: C₁₅H₁₅NO₂
• Molecular Weight: 241.29
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Chiral Compound;a-amino
• Mol File: 155760-02-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 428.6 °C at 760 mmHg
• Flash Point: 213 °C
• Appearance: White fine crystals
• Density: 1.19 g/cm³
• Vapor Pressure: 8.52E-14mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: Store at RT.
• Solubility: Acidic DMSO (Slightly)
• PKA: 2.21±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: L-4,4'-BIPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-4,4'-BIPHENYLALANINE(155760-02-4)
• EPA Substance Registry System: L-4,4'-BIPHENYLALANINE(155760-02-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 155760-02-4(Hazardous Substances Data)

Usage

Description

L-4,4'-BIPHENYLALANINE is an amino acid derivative that possesses unique structural and functional properties. It is characterized by the presence of a biphenyl group attached to the alpha-carbon of the alanine molecule, which distinguishes it from other amino acids. This structural feature endows L-4,4'-BIPHENYLALANINE with potential applications in various fields, particularly in the synthesis of biologically active small molecules.

Uses

Used in Pharmaceutical Industry:
L-4,4'-BIPHENYLALANINE is used as a building block for the synthesis of various biologically active small molecules, such as peptides, peptidomimetics, and other bioactive compounds. Its unique structural properties allow for the development of novel therapeutic agents with potential applications in the treatment of various diseases and conditions.
Used in Chemical Research:
L-4,4'-BIPHENYLALANINE serves as a valuable reagent in chemical research, particularly in the field of organic synthesis. Its distinct structural features make it an attractive candidate for the development of new synthetic methods and strategies, as well as for the exploration of its potential as a chiral auxiliary or ligand in asymmetric catalysis.
Used in Material Science:
The unique structural properties of L-4,4'-BIPHENYLALANINE also make it a promising candidate for the development of novel materials with specific properties, such as optoelectronic materials, sensors, or self-assembling systems. Its incorporation into polymers or other materials could lead to the creation of new materials with enhanced performance characteristics.

InChI:InChI=1/C18H20N2O4/c19-15(17(21)22)9-11-1-5-13(6-2-11)14-7-3-12(4-8-14)10-16(20)18(23)24/h1-8,15-16H,9-10,19-20H2,(H,21,22)(H,23,24)/t15-,16-/m0/s1

Upstream product

• 1432516-20-5 C₂₉H₃₄N₄O₄ 
• 62129-39-9 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine 
• 98-80-6 phenylboronic acid 
• 119273-61-9 N-tert-butoxycarbonyl-p-phenyl-L-phenylalanine 
• 24250-84-8 H-p-BrPhe-OH 
• 13026-23-8 (2E)-3-(1,1'-biphenyl-4-yl)acrylic acid 
• 76985-08-5 α-amino-(1,1'-biphenyl)-4-propanoic acid 
• 199110-64-0 (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid 
• 198561-04-5 Fmoc-4-bromo-L-phenylalanine 

Downstream Products

• 139040-51-0 methyl (S)-2-amino-3-(biphenyl-4-yl)propanoate 
• 63024-30-6 (S)-2-amino-3-(biphenyl-4-yl)-propionic acid methyl ester hydrochloride 
• 225528-25-6 tert-butyl (2S)-2-amino-3-(4-phenylphenyl)propanoate 
• 270568-72-4 2-benzyloxycarbonylamino-3-biphenyl-4-ylpropionic acid 
• 119273-61-9 N-tert-butoxycarbonyl-p-phenyl-L-phenylalanine 

Relevant articles and documents

Constraining the Side Chain of C-Terminal Amino Acids in Apelin-13 Greatly Increases Affinity, Modulates Signaling, and Improves the Pharmacokinetic Profile

Side-chain-constrained amino acids are useful tools to modulate the biological properties of peptides. In this study, we applied side-chain constraints to apelin-13 (Ape13) by substituting the Pro12 and Phe13 positions, affecting the binding affinity and signaling profile on the apelin receptor (APJ). The residues 1Nal, Trp, and Aia were found to be beneficial substitutions for Pro12, and the resulting analogues displayed high affinity for APJ (Ki 0.08-0.18 nM vs Ape13 Ki 0.7 nM). Besides, constrained (d-Tic) or α,α-disubstituted residues (Dbzg; d-α-Me-Tyr(OBn)) were favorable for the Phe13 position. Compounds 47 (Pro12-Phe13 replaced by Aia-Phe, Ki 0.08 nM) and 53 (Pro12-Phe13 replaced by 1Nal-Dbzg, Ki 0.08 nM) are the most potent Ape13 analogues activating the Gα12 pathways (53, EC50 Gα12 2.8 nM vs Ape13, EC50 43 nM) known to date, displaying high affinity, resistance to ACE2 cleavage as well as improved pharmacokinetics in vitro (t1/2 5.8-7.3 h in rat plasma) and in vivo.

Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky l- and d-Arylalanines

Tailored mutants of phenylalanine ammonia-lyase from Petroselinum crispum (PcPAL) were created and tested in ammonia elimination from various sterically demanding, non-natural analogues of phenylalanine and in ammonia addition reactions into the corresponding (E)-arylacrylates. The wild-type PcPAL was inert or exhibited quite poor conversions in both reactions with all members of the substrate panel. Appropriate single mutations of residue F137 and the highly conserved residue I460 resulted in PcPAL variants that were active in ammonia elimination but still had a poor activity in ammonia addition onto bulky substrates. However, combined mutations that involve I460 besides the well-studied F137 led to mutants that exhibited activity in ammonia addition as well. The synergistic multiple mutations resulted in substantial substrate scope extension of PcPAL and opened up new biocatalytic routes for the synthesis of both enantiomers of valuable phenylalanine analogues, such as (4-methoxyphenyl)-, (napthalen-2-yl)-, ([1,1′-biphenyl]-4-yl)-, (4′-fluoro-[1,1′-biphenyl]-4-yl)-, and (5-phenylthiophene-2-yl)alanines.

Design, synthesis, and bioevaluation of viral 3C and 3C-like protease inhibitors

A class of tripeptidyl transition state inhibitors containing a P1 glutamine surrogate, a P2 leucine, and a P3 arylalanines, was found to potently inhibit Norwalk virus replication in enzyme and cell based assays. An array of warheads, including aldehyde, α-ketoamide, bisulfite adduct, and α-hydroxyphosphonate transition state mimic, was also investigated. Tripeptidyls 2 and 6 possess antiviral activities against noroviruses, human rhinovirus, severe acute respiratory syndrome coronavirus, and coronavirus 229E, suggesting a broad range of antiviral activities.