147923-08-8

Basic information

• Product Name: BOC-L-4,4'-BIPHENYLALANINE
• Synonyms: 3-(4-BIPHENYLYL)-N-(T-BUTOXYCARBONYL)-L-ALANINE;3-(4-BIPHENYLYL)-N-(TERT-BUTOXYCARBONYL)-L-ALANINE;(S)-2-(BOC-AMINO)-3-(4-BIPHENYLYL)PROPIONIC ACID;(S)-3-BIPHENYL-4-YL-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID;(S)-N-ALPHA-T-BUTYLOXYCARBONYL-BIPHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-L-(4-PHENYL)PHENYLALANINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-BIPHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-4,4'-BIPHENYL-L-ALANINE
• CAS NO: 147923-08-8
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Biphenyl & Diphenyl ether;Amino Acid Derivatives;a-amino
• Mol File: 147923-08-8.mol

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 528.2 °C at 760 mmHg
• Flash Point: 273.2 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 2.33E-12mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.88±0.10(Predicted)
• CAS DataBase Reference: BOC-L-4,4'-BIPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-4,4'-BIPHENYLALANINE(147923-08-8)
• EPA Substance Registry System: BOC-L-4,4'-BIPHENYLALANINE(147923-08-8)

Safety Data

• Hazard Codes: N,Xi,Xn
• Statements: 50/53-41-38-20/22-63
• Safety Statements: 60-61-36-26-36/37
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 147923-08-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-L-4,4'-BIPHENYLALANINE is used as a reactant for the synthesis of novel phenylalanines derived diamides. These diamides serve as factor XIa inhibitors, which are used in the treatment of various medical conditions. The compound plays a crucial role in the development of new therapeutic agents that can potentially improve patient outcomes.

InChI:InChI=1/C21H25NO4/c1-21(2,3)26-20(25)22-18(19(24)14-23)13-15-9-11-17(12-10-15)16-7-5-4-6-8-16/h4-12,18,23H,13-14H2,1-3H3,(H,22,25)

Upstream product

• 137255-86-8 methyl (S)-3-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 98-80-6 phenylboronic acid 
• 62129-39-9 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 24250-84-8 H-p-BrPhe-OH 
• 266306-18-7 (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 155760-02-4 (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid 

Downstream Products

• 1026595-70-9 {(S)-1-[(S)-1-((S)-1-Benzyl-3-chloro-2-oxo-propylcarbamoyl)-2-carbamoyl-ethylcarbamoyl]-2-biphenyl-4-yl-ethyl}-carbamic acid tert-butyl ester 
• 155873-50-0 (S)--β-alanine benzyl ester 
• 200864-86-4 [(S)-2-Biphenyl-4-yl-1-(3-morpholin-4-yl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 200864-88-6 {(S)-2-Biphenyl-4-yl-1-[2-(4-hydroxy-phenyl)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 200864-90-0 [(S)-2-Biphenyl-4-yl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

A self-assembling NHC-PD-loaded calixarene as a potent catalyst for the Suzuki-Miyaura cross-coupling reaction in water

Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 40-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance.

Selective modification of a native protein in a patient tissue homogenate using palladium nanoparticles

We have developed new benign palladium nanoparticles able to catalyze the Suzuki-Miyaura cross-coupling reaction on human thyroglobulin (Tg), a naturally iodinated protein produced by the thyroid gland, in homogenates from patients' tissues. This represents the first example of a chemoselective native protein modification using transition metal nanoobjects in near-organ medium.

Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters

A number of cyanomethyl esters of natural/unnatural aminoacids with un-protected amino functionality were synthesized because of their synthetic and medicinal importance. Critical N-Boc deprotection methods in the presence of labile (hydrolytic sensitivity) cyanomethyl functionality were screened thoroughly and it was found that readily available 4M HCl in 1,4-dioxane solution (2–4 equiv); acetonitrile, 0 °C, 2–4 h was a suitable condition. This condition was generalized and successfully applied to a variety of alkyl, alkynyl, aryl, heteroaryl, benzyl, azido, spiro amino acid cyanomethylesters irrespective of the nature of the amine (primary or secondary) and the distance between the amine and ester group to achieve final deprotected amino esters with high yield, and purity compared to other commonly known N-protecting groups (Cbz, Fmoc, Ac, Bn, Bz etc.). It was also demonstrated that N-Boc protected aminoacid cyanomethylesters are stable enough to carry out further functionalization compared to N-unprotected counterparts.

Improved binding affinities of pyrrolidine derivatives as Mcl-1 inhibitors by modifying amino acid side chains

As an important member of anti-apoptotic Bcl-2 protein, myeloid cell leukemia sequence 1 (Mcl-1) protein is an attractive target for cancer therapy. In this study, a new series of pyrrolidine derivatives as Mcl-1 inhibitors were developed by mainly modifying the amino acid side chain of compound 1. Among them, compound 18 (Ki= 0.077 μM) exhibited better potent inhibitory activities towards Mcl-1 protein compared to positive control Gossypol (Ki= 0.18 μM). In addition, compound 40 possessed good antiproliferative activities against PC-3 cells (Ki= 8.45 μM), which was the same as positive control Gossypol (Ki= 7.54 μM).

PLGA-PEG-supported Pd nanoparticles as efficient catalysts for Suzuki-Miyaura coupling reactions in water

Chemical transformations that can be performed selectively under physiological conditions are highly desirable tools to track biomolecules and manipulate complex biological processes. Here, we report a new nanocatalyst consisting of small palladium nanoparticles stabilized on the surface of PLGA-PEG nanoparticles that show excellent catalytic activity for the modification of biological building blocks through Suzuki-Miyaura cross-coupling reactions in water. Brominated or iodinated amino acids were coupled with aryl boronic acids in phosphate buffer in good yields. Interestingly, up to 98% conversion into the coupled amino acid could be achieved in 2 h at 37°C using the stable, water-soluble cyclic triolborate as organometallic partner in the presence of only 1 mol% of palladium. These results pave the way for the modification of biomolecules in complex biological systems such as the intracellular space.

Suzuki-Miyaura Diversification of Amino Acids and Dipeptides in Aqueous Media

The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with considerable potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that although asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.

Chemoenzymatic Synthesis of Optically Pure l- and d-Biarylalanines through Biocatalytic Asymmetric Amination and Palladium-Catalyzed Arylation

A chemoenzymatic approach was developed and optimized for the synthesis of a range of N-protected nonnatural l- and d-biarylalanine derivatives. Starting from 4-bromocinnamic acid and 4-bromophenylpyruvic acid using a phenylalanine ammonia lyase (PAL) and an evolved d-amino acid dehydrogenase (DAADH), respectively, both enantiomers of 4-bromophenylalanine were obtained and subsequently coupled with a panel of arylboronic acids to give the target compounds in high yield and optical purity under mild aqueous conditions.

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.

A convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling

(Figure Presented) A phosphine-free palladium catalyst for aqueous Suzuki-Miyaura cross-coupling is presented. The catalyst is active enough to mediate hindered, ortho-substituted biaryl couplings but mild enough for use on peptides and proteins. The Suzuki-Miyaura couplings on protein substrates are the first to proceed in useful conversions. Notably, hydrophobic aryl and vinyl groups can be transferred to the protein surface without the aid of organic solvent since the aryl- and vinylboronic acids used in the coupling are water-soluble as borate salts. The convenience and activity of this catalyst prompts use in both general synthesis and bioconjugation.

PHOSPHONO SUBSTITUTED TETRAZOLE DERIVATIVES AS ECE INHIBITORS

The present invention relates to the N-phosphonomethyl substituted compounds of formula STR1