128779-47-5

Usage

Uses

Used in Peptide Chemistry:
BOC-D-4,4'-BIPHENYLALANINE is used as a building block for the synthesis of peptides, allowing for the creation of novel peptide sequences with tailored properties. Its unique 4,4'-biphenyl moiety contributes to the structural diversity and functional characteristics of the resulting peptides.
Used in Drug Development:
In the pharmaceutical industry, BOC-D-4,4'-BIPHENYLALANINE is used as a key component in the design and synthesis of new drugs. Its ability to modulate peptide and protein structures makes it a valuable asset in the development of therapeutic agents with specific biological activities.
Used in Medicinal Chemistry:
BOC-D-4,4'-BIPHENYLALANINE is employed as a research tool in medicinal chemistry to explore the interactions between peptides, proteins, and other biomolecules. Its incorporation into peptide sequences can provide insights into the mechanisms of action and potential therapeutic applications of these molecules.
Used in Materials Science:
BOC-D-4,4'-BIPHENYLALANINE is used as a component in the development of advanced materials with specific properties, such as self-assembling systems, biocompatible coatings, and stimuli-responsive materials. Its unique structural features and reactivity contribute to the creation of innovative materials with potential applications in various fields.

InChI:InChI=1/C20H23NO4/c1-20(2,3)25-19(24)21-17(18(22)23)16(14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13,16-17H,1-3H3,(H,21,24)(H,22,23)/t17-/m1/s1

Upstream product

• 4530-20-5 BOC-glycine 
• 3218-36-8 4-Phenylbenzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1057002-37-5 4-[1-biphenyl-4-yl-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one 
• 1188995-14-3 (Z)-4-([1,10-biphenyl]-4-ylmethylene)-2-methyloxazol-5(4H)-one 
• 91853-46-2 3-([1,1'-biphenyl]-4-yl)-2-oxopropanoic acid 
• 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 
• 155760-02-4 (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid 
• 266306-18-7 (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 62129-39-9 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 24250-84-8 H-p-BrPhe-OH 

Downstream Products

• 1426129-50-1 N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester 
• 149709-59-1 (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester 
• 149709-60-4 ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate 
• 752174-62-2 (2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester 
• 155873-50-0 (S)--β-alanine benzyl 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 
• 153037-40-2 (S)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propan-1-ol 
• 155760-02-4 (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid 
• 872341-97-4 [(S)-1-Biphenyl-4-ylmethyl-2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Developing Equipotent Teixobactin Analogues against Drug-Resistant Bacteria and Discovering a Hydrophobic Interaction between Lipid II and Teixobactin

Teixobactin, targeting lipid II, represents a new class of antibiotics with novel structures and has excellent activity against Gram-positive pathogens. We developed a new convergent method to synthesize a series of teixobactin analogues and explored structure-activity relationships. We obtained equipotent and simplified teixobactin analogues, replacing the l-allo-enduracididine with lysine, substituting oxygen to nitrogen on threonine, and adding a phenyl group on the d-phenylalanine. On the basis of the antibacterial activities that resulted from corresponding modifications of the d-phenylalanine, we propose a hydrophobic interaction between lipid II and the N-terminal of teixobactin analogues, which we map out with our analogue 35. Finally, a representative analogue from our series showed high efficiency in a mouse model of Streptococcus pneumoniae septicemia.

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.

Sacubitril intermediate as well as synthesis method and application thereof

The invention belongs to the technical field of medicine, and particularly relates to a sacubitril intermediate and a synthetic method and application thereof, wherein the synthetic method comprises the steps: taking D-biphenyl alanine as an initial raw material, and successively carrying out multiple reactions; and crystallizing and filtering to obtain (R)-2-(N-tert-butyloxycarbonylamino)biphenylpropanol. According to the sacubitril intermediate and the synthetic method and application thereof disclosed by the invention, D-biphenyl alanine is selected as an initial raw material; the subsequent added reactants are combined for successive reaction for multiple times; and finally, (R)-2-(N-tert-butyloxycarbonylamino)biphenyl propanol is synthesized. The reaction steps are simple and environment-friendly; industrial production is facilitated, particularly, the chemical purity of the product can reach 96% or above; the yield can reach 85% or above, and good industrial prospects are achieved; in addition, according to the synthetic method of (R)-2-(N-tert-butyloxycarbonylamino)biphenyl propanol, the recycled metal catalyst and concentrated filtrate can be recycled, the synthesis cost of (R)-2-(N-tert-butyloxycarbonylamino)biphenyl propanol is low, and industrial production is better facilitated.

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.

NEW PROCESS FOR EARLY SACUBITRIL INTERMEDIATES

The invention relates to a new enantioselective process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone.

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).

Preparation method and application of high-optical-purity biphenylalanine and derivative thereof

The invention relates to a preparation method and application of high-optical-purity biphenylalanine and a derivative thereof. The preparation method employs an acidic resolution reagent and controls the pH value of a reaction so as to prepare a target compound. According to the invention, raw materials are simple, easily available and cheap; the product obtained after resolution has high optical purity, so the problem of a final product with high optical purity is hard to prepare through refining in the prior art; and the preparation method is simple to operate, high in security, and low in the usage amount of wastewater and energy consumption, can overcome EHS problems in drug development, and is suitable for industrial large-scale production.

Preparation method of (R)-2-(N-tertbutyloxycarbonylamino)biphenylpropanol

The invention discloses a preparation method of (R)-2-(N-tertbutyloxycarbonylamino)biphenylpropanol represented by formula (I). The method comprises the following steps: carrying out an Erlenmeyer-Plochl cyclization reaction on biphenylcarboxaldehyde and N-acylglycine, hydrolyzing or alcoholyzing, and carrying out asymmetric hydrogenation to obtain (R)-N-acylbiphenylalanine or an ester thereof; and carrying out acid hydrolysis, reduction and amino protection on the (R)-N-acylbiphenylalanine or the ester thereof, or carrying out reduction, acid hydrolysis and amino protection on the (R)-N-acylbiphenylalanine or the ester thereof, or directly reducing the (R)-N-acylbiphenylalanine or the ester thereof in order to obtain the product (R)-2-(N-tertbutyloxycarbonylamino)biphenylpropanol. The product is a key intermediate of Sacubitril (AHU-377) which is one of a novel blood pressure reducing medicine LCZ696. The method has the advantages of easily available raw materials, and suitableness for industrial production.

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.