82310-97-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-AMINO-4-(4-METHOXY-PHENYL)-BUTYRIC ACID is used as an intermediate in the synthesis of various pharmaceuticals for its unique structural properties that can be leveraged to create novel drugs with specific therapeutic effects.
Used as a Chiral Building Block in Organic Synthesis:
In the field of organic chemistry, (S)-2-AMINO-4-(4-METHOXY-PHENYL)-BUTYRIC ACID is used as a chiral building block for the development of enantiomerically pure compounds, which are essential in the creation of drugs with targeted effects and reduced side effects.
Used in Medical Applications:
L-Phenylglycine has potential applications in the medical industry, where it can be utilized in the development of new therapeutic agents, particularly those that require a specific stereochemistry for their mode of action.
Used in Agricultural Applications:
In agriculture, (S)-2-AMINO-4-(4-METHOXY-PHENYL)-BUTYRIC ACID may be employed in the development of compounds that can enhance crop protection, acting as additives in pesticides or fertilizers, or as components in the synthesis of plant growth regulators.
Used in Manufacturing Industry:
The manufacturing industry can benefit from L-Phenylglycine's properties, using it in the production of specialty chemicals, materials, or as a component in the formulation of various industrial products that require its specific characteristics.

Upstream product

• 112741-55-6 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 728925-59-5 N-[(2E)-4-(4-methoxyphenyl)-4-oxobut-2-enoyl]-L-leucine 
• 728925-56-2 1-{[(2E)-4-(4-methoxyphenyl)-4-oxobut-2-enoyl]oxy}pyrrolidine-2,5-dione 
• 82267-39-8 diethyl<2-(p-methoxyphenyl)ethyl>(acetamido)malonate 
• 82267-42-3 <2-(p-methoxyphenyl)ethyl>(acetamido)malonic acid 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 14425-64-0 4-methoxyphenethyl bromide 
• 82310-95-0 (R)-2-Acetylamino-4-(4-methoxy-phenyl)-butyric acid 
• 728925-58-4 N-[(2E)-4-(4-methoxyphenyl)-4-oxobut-2-enoyl]-L-phenylalanine 
• 696-62-8 para-iodoanisole 
• 346722-43-8 (S)-2-((R)-1-Hydroxymethyl-propylamino)-4-(4-methoxy-phenyl)-4-oxo-butyric acid 
• 20972-37-6 (E)-4-(4-methoxyphenyl)-4-oxo-2-butenoic acid 
• 346722-47-2 (S)-2-((R)-1-Hydroxymethyl-propylamino)-4-(4-methoxy-phenyl)-butyric acid 
• 212010-24-7 (αS,1S)-α-[N-(1-methyl)benzyl]-β-[4'-(methoxy)benzoyl]alanine 

Downstream Products

• 87423-12-9 Boc-L-Ala-L-Hmb-L-Amb-OH 

Relevant academic research and scientific papers

METHOD FOR PREPARING AROMATIC AMINO ACID DERIVATIVE

The present invention provides methods of efficiently producing various optically active aromatic amino acid derivatives by reacting, using an additive, a specific ester compound with an aromatic halide and zinc in the presence of a catalyst. The present invention also provides amino acid derivatives that can be produced by the methods.

Inhibition of tyrosine phenol-lyase by tyrosine homologues

We have designed, synthesized, and evaluated tyrosine homologues and their O-methyl derivatives as potential inhibitors for tyrosine phenol lyase (TPL, E.C. 4.1.99.2). Recently, we reported that homologues of tryptophan are potent inhibitors of tryptophan indole-lyase (tryptophanase, TIL, E.C. 4.1.99.1), with Ki values in the low μM range (Do et al. Arch Biochem Biophys 560:20–26, 2014). As the structure and mechanism for TPL is very similar to that of TIL, we postulated that tyrosine homologues could also be potent inhibitors of TPL. However, we have found that homotyrosine, bishomotyrosine, and their corresponding O-methyl derivatives are competitive inhibitors of TPL, which exhibit Ki values in the range of 0.8–1.5?mM. Thus, these compounds are not potent inhibitors, but instead bind with affinities similar to common amino acids, such as phenylalanine or methionine. Pre-steady-state kinetic data were very similar for all compounds tested and demonstrated the formation of an equilibrating mixture of aldimine and quinonoid intermediates upon binding. Interestingly, we also observed a blue-shift for the absorbance peak of external aldimine complexes of all tyrosine homologues, suggesting possible strain at the active site due to accommodating the elongated side chains.

Changing the selectivity profile–from substrate analog inhibitors of thrombin and factor Xa to potent matriptase inhibitors

The type II transmembrane serine protease matriptase is a potential target for anticancer therapy and might be involved in cartilage degradation in osteoarthritis or inflammatory skin disorders. Starting from previously described nonspecific thrombin and factor Xa inhibitors we have prepared new noncovalent substrate-analogs with superior potency against matriptase. The most suitable compound 35 (H-d-hTyr-Ala-4-amidinobenzylamide) binds to matriptase with an inhibition constant of 26 nM and has more than 10-fold reduced activity against thrombin and factor Xa. The crystal structure of inhibitor 35 was determined in the surrogate protease trypsin, the obtained complex was used to model the binding mode of inhibitor 35 in the active site of matriptase. The methylene insertion in d-hTyr and d-hPhe increases the flexibility of the P3 side chain compared to their d-Phe analogs, which enables an improved binding of these inhibitors in the well-defined S3/4 pocket of matriptase. Inhibitor 35 can be used for further biochemical studies with matriptase.

Crystallisation-induced asymmetric transformation (CIAT) for the synthesis of dipeptides containing homophenylalanine

A novel synthesis of highly enantioenriched dipeptides containing homophenylalanine is described. The process involves a crystallisation-induced asymmetric transformation (CIAT) in a Michael addition followed by exhaustive reduction. A unique example of a formally stereodivergent CIAT in conjugate addition of an achiral N-nucleophile to enantiomerically pure Michael acceptor has been discovered.

A novel β-amino acid in cytotoxic peptides from the cyanobacterium Tychonema sp.

The cyclic dodecapeptides tychonamide A (1) and B (2) isolated from the methanolic extract of the cyanobacterium Tychonema sp. contain the novel β-amino acid 3-amino-2,5,7-trihydroxy-8-phenyloctanoic acid (Atpoa). Compounds 1 and 2 have cytotoxic activity

Crystallization-induced asymmetric transformations (CIAT): Stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids

Acid-catalyzed lactonization in dilute hydrochloric acid of N-substituted 2-amino-4-aryl-4-hydroxybutanoic acids with electron donating aryl substituents is stereoconvergent. The stereochemical outcome is controlled by the precipitation of little soluble

Crystallization-induced dynamic resolution (CIDR) and its application to the synthesis of unnatural N-substituted amino acids derived from aroylacrylic acids

A highly stereoselective conjugate addition of chiral amino alcohols affords a simple and inexpensive access to a wide variety of N-functionalized homophenylalanine derivatives. Limitations and conditions for application of CIDR to this system were studied.

Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives

(R and S)-α-Amino alcohols and α-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant α-amino alcohols are described.

γ-oxo-homophenylalanine derivatives and process for producing homophenylalanine derivatives by reducing the same

The present invention provides an economically advantageous and efficient process for producing an optically active homophenylalanine derivative of the general formula (IV), and an intermediate therefor and a process for producing it. The present invention relates to a process for producing homophenylalanine derivative of the general formula (IV) which comprises reacting a β-benzoylacrylic acid derivative of the general formula (II) with a 1-arylethylamine derivative of the general formula (III) and reducing the resultant γ-oxo-homophenylalanine derivative of the general formula (I). STR1

Synthesis of optically active (2-arylvinyl)glycine derivatives by palladium-catalyzed arylation of (s)-n-(benzyloxycarbonyl)vinylglycine

Phenyl, tolyl, anisyl, and 1-naphthyl iodides (7a-g,n) smoothly reacted with (S)-N-(benzyloxycarbonyl)-vinylglycine (6) in H2O in the presence of Pd(OAc)2, Bu4NCI, and NaHCO3 at 45°C, producing [S-(E)]-(2- arylvinyl)glycine derivatives 8a-g, n of high enantiomeric purity. The yields of the reactions of 3- (7f), 2- (7e), and 4-iodoanisoles (7g) increased in this order. This relationship between the yield and the position of substitution has been found to hold for bromophenyl iodides (7i-k), although somewhat lower chemical and optical yields were realized in these cases. Phenyl iodide 71 carrying an electron-withdrawing 4-acetyl group gave an unsatisfactory result, and more electron-deficient 4-nitrophenyl iodide (7m) did not provide the desired product. All these results suggest that the reaction is advantageous with electron-sufficient substrates 7. However, this was not the case for 4-iodophenol (7h), as well as some heterocyclic iodides.