Syntheses of 6-fluoro-meta-tyrosine and of its metabolites

Konkel, Jamie; Fan, Junfeng; Jayachandran, B.; Kirk, Kenneth L.

doi:10.1016/s0022-1139(02)00013-1

Cited by 26 publications

(10 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fluorophenols can serve as synthons for the production of drugs, including enzyme inhibitors [2,3] and receptor antagonists. [4] Catecholamines and amino acids with a radiolabelled [ 18 F]-fluorophenol moiety have found applications for the in vivo imaging of amino acid metabolism [5] and protein synthesis [6] using positron emission tomography (PET). [7] Chemical methods to produce fluorophenols include diazotization/Sandmeyer decomposition with fluoroanilines, diazotization/thermal decomposition with aminophenols, alkaline hydrolysis with substituted fluorobenzene and F 2 /N 2 gas/liquid phase conversion with phenol.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Baeyer–Villiger Oxidation of Benzaldehydes

Moonen¹,

Westphal²,

Rietjens

et al. 2005

Adv Synth Catal

View full text Add to dashboard Cite

The selectivity of the chemical Baeyer-Villiger oxidation of benzaldehydes depends on steric and electronic factors, the type of oxidizing agent and the reaction conditions. Here we report on the enzymatic Baeyer-Villiger oxidation of fluorobenzaldehydes as catalyzed by the flavoprotein 4-hydroxyacetophenone monooxygenase (HAPMO). HAPMO was most active with 4-amino-and 4-hydroxybenzaldehydes. With these compounds significant substrate inhibition occurred. Monofluoro-and difluorobenzaldehydes were readily oxidized by HAPMO without substrate inhibition. 19F NMR analysis revealed that 4-fluoro-, 2,6-difluoro-, 3,4-difluoro-, 2-fluoro-4-hydroxy-and 3-fluoro-4-hydroxybenzaldehyde were quantitatively converted by HAPMO to the corresponding fluorophenyl formates. These products spontaneously hydrolyzed to fluorophenols. The HAPMO-mediated conversion of 2-fluoro-, 3-fluoro-, 2,3-difluoro-and 2,4-difluorobenzaldehyde yielded, besides fluorophenols, also minor amounts of fluorobenzoic acids. The high preference of HAPMO for the production of fluorophenols is in disagreement with the rule derived from chemical studies that electron-poor benzaldehydes form mainly benzoic acids. This suggests that interactions of the benzaldehyde substrates with amino acids and/or the flavin cofactor in the enzyme active site influence the selection of the migratory group in favor of the phenyl ring.

show abstract

Section: Introductionmentioning

confidence: 99%

Enzymatic Baeyer–Villiger Oxidation of Benzaldehydes

Moonen¹,

Westphal²,

Rietjens

et al. 2005

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…Several methods of synthesis for halogenated meta-tyrosine or tyrosine were previously proposed (Bovonsombat et al 2008, Drain &Howes 1967, Kirk et al 1986, Konkel et al 2002. Fluorinated analogues and particularly 6-fluoro-meta-tyrosine (Table 1, 8d) was synthesized to use it as a tracer for medical imaging (Konkel et al 2002, VanBrocklin et al 2004, Vasdev et al 2001. Halogenated m-tyrosine derivatives were found to lower the blood pressure of mammals (Drain &Howes 1967).…”

Section: Synthesis Of Halogenated Analogues Of M-tyrosinementioning

confidence: 99%

“…Halogenated m-tyrosine derivatives were found to lower the blood pressure of mammals (Drain &Howes 1967). Finally, we chose the synthesis in seven steps proposed by Konkel et al (Kirk et al 1986, Konkel et al 2002 and among the nine products that were synthesized (Table 1), six were new (compounds 8a, 8b, 8e, 8f, 8h and 8i). The first six steps were performed with good to very good yields, whose median is between 65% (steps 2 and 4) and 95% (step 6).…”

Section: Synthesis Of Halogenated Analogues Of M-tyrosinementioning

confidence: 99%

Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine

Movellan

Rocher

Chikh

et al. 2012

Environ Sci Pollut Res

View full text Add to dashboard Cite

L-meta-tyrosine is an herbicidal nonprotein amino acid isolated some years ago from fine fescue grasses and characterized by its almost immediate microbial degradation in soil (half-life <24 h). Nine monohalogenated or dihalogenated analogs of this allelochemical have been obtained through a seven-step stereoselective synthesis from commercial halogenated phenols. Bioassays showed a large range of biological responses, from a growth root inhibition of lettuce seedling similar to that noted with m-tyrosine [2-amino-3-(2-chloro-5-hydroxyphenyl)propanoic acid or compound 8b] to an increase of the primary root growth concomitant with a delay of secondary root initiation [2-amino-3-[2-fluoro-5-hydroxy-3-(trifluoromethyl)phenyl]propanoic acid or compound 8h]. Compound 8b was slightly less degraded than m-tyrosine in the nonsterilized nutritive solution used for lettuce development, while the concentration of compound 8h remained unchanged for at least 2 weeks. These data indicate that it is possible to manipulate both biological properties and degradation of m-tyrosine by halogen addition.

show abstract

“…[1] They are particularly useful precursors for the synthesis of aminoacids, [2] peptides, [3] heterocycles, [4] N-substituted pyrroles, [5] biosensors [6] and antitumor [7] or anticancer [8] compounds. Hence, synthesis of this heterocyclic nucleus is of continuing interest.…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al₂O₃Under Solvent-Free Conditions

Rostamizadeh

Khajeh‐Amiri

Moghanian

2015

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

View full text Add to dashboard Cite

MgO/Al 2 O 3 catalyzes the synthesis of azlactone derivatives from condensation reaction of aldehydes (or ketones) with hippuric acid and acetic anhydride as a dehydrating agent under microwave irradiation. The low toxicity, low cost, ease of handling and high activity of MgO/Al 2 O 3 make this procedure particularly attractive. Also, this catalyst can be easily recovered by decant and can be reused for this condensation five times in succession without considerable loss of its catalytic activity.

show abstract

Syntheses of 6-fluoro-meta-tyrosine and of its metabolites

Cited by 26 publications

References 7 publications

Enzymatic Baeyer–Villiger Oxidation of Benzaldehydes

Enzymatic Baeyer–Villiger Oxidation of Benzaldehydes

Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine

Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al₂O₃Under Solvent-Free Conditions

Contact Info

Product

Resources

About

Syntheses of 6-fluoro-meta-tyrosine and of its metabolites

Cited by 26 publications

References 7 publications

Enzymatic Baeyer–Villiger Oxidation of Benzaldehydes

Enzymatic Baeyer–Villiger Oxidation of Benzaldehydes

Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine

Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al2O3Under Solvent-Free Conditions

Contact Info

Product

Resources

About

Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al₂O₃Under Solvent-Free Conditions