82311-00-0

Basic information

• Product Name: O-methyl-L-homotyrosine
• Synonyms: O-methyl-L-homotyrosine
• CAS NO: 82311-00-0
• Molecular Weight: 209.245
• Mol File: 82311-00-0.mol

Chemical Properties

• CAS DataBase Reference: O-methyl-L-homotyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: O-methyl-L-homotyrosine(82311-00-0)
• EPA Substance Registry System: O-methyl-L-homotyrosine(82311-00-0)

Safety Data

• Hazardous Substances Data: 82311-00-0(Hazardous Substances Data)

Upstream product

• 696-62-8 para-iodoanisole 
• 728925-58-4 N-[(2E)-4-(4-methoxyphenyl)-4-oxobut-2-enoyl]-L-phenylalanine 
• 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 
• 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 
• 171077-29-5 -2-<(benzyloxycarbonyl)amino>-4-(4-methoxyphenyl)-3-butenoic acid 
• 82267-44-5 DL-2-acetamido-4-(p-methoxyohenyl)butanoic acid 
• 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 

Downstream Products

• 110936-12-4 N-(methylcarbamoyl)homotyrosine methyl ester 
• 221243-01-2 (S)-homotyrosine 
• 87423-16-3 D-A₂pr(Z)-L-Ala-L-Hmb-L-Amb-ONSu trifluoroacetic acid 
• 92837-10-0 Boc-D-A₂pr(Z)-L-Ala-L-Hmb-L-Amb-ONSu 
• 87423-14-1 Boc-D-A₂pr(Z)-L-Ala-L-Hmb-L-Amb-OH 
• 87423-13-0 L-Ala-L-Hmb-L-Amb-OH hydrochloride 
• 87423-12-9 Boc-L-Ala-L-Hmb-L-Amb-OH 

Relevant articles and documents

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.

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 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.

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.

A highly efficient asymmetric synthesis of methoxyhomophenylalanine using Michael addition of phenethylamine

A practical method for (S)-p-methoxyhomophenylalanine (S)-1 by using diastereoselective Michael addition as a key step was reported. Thus, the Michael addition of (S)-1-phenethylamine (S)-3 to p-methoxy-trans- benzoylacrylic acid 2 was performed in a high

The Heck reaction of N-protected vinylglycines with 4-iodoanisole

Among N-protected and unprotected vinylglycines tested, N-(benzyloxycarbonyl)vinylglycine (1c) provided the highest yield of the coupling product 3c in the reaction with 1-iodo-4-methoxybenzene (2) in N,N-dimethylformamide in the presence of palladium acetate, sodium bicarbonate, and tetrabutylammonium chloride, whereas none of the desired product was obtained in the reaction with 4-methoxyphenyl trifluoromethanesulfonate (7). The stereo-selectivity of the reaction was reversed by employing triethylamine instead of sodium bicarbonate to furnish (Z)-3c predominantly. In the presence of sodium bicarbonate, replacement of the solvent by water improved not only the chemical yield and stereo-selectivity but also the optical purity: geometiically pure (E)-3c of 96% ee was formed in a good yield.

Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates

The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.

PREPARATION OF HOMOLOGS OF L-2-AMINO-5-(p-METOXYPHENYL)PENTANOIC ACID

Lower and higher homologs, L-2-amino-4-(p-methoxyphenyl)butanoic acid (L-amb) and L-2-amino-6-(p-methoxyphenyl)hexanoic acid (L-Amh), of L-2-amino-5-(p-methoxyphenyl)pentanoic acid were prepared by optical resolution of N-acetyl-DL-Amb and of N-acetyl-DL-Amh with Aspergillus acylase.N-acetyl DL-Amb or N-acetyl-DL-Amh was synthesized from (acetamido malonic acid by heating with p-xylene.