Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement
نویسندگان
چکیده
منابع مشابه
Stereocontrolled synthesis of kelsoene by the homo-favorskii rearrangement.
[reaction: see text] (+/-)-Kelsoene (4) has been synthesized from 2,5-dihydroanisole in 16 steps in 12.5% overall yield. The key step involves a base-catalyzed reaction of gamma-keto tosylate (5), which effects a homo-Favorskii rearrangement to 16 as well as the corresponding intramolecular S(N)2 product 15 from the enolate of 5. Ketone 15 can efficiently be isomerized to cyclobutanone 17 havin...
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We report a new approach for the detection of mitochondrial flavins through photo-oxidation of a probe molecule. Probe 1 showed high brightness (ε × Φf = 6.50 × 103 M-1 cm-1) at long wavelengths (maximum emission wavelength, λmax = 600 nm) upon photo-oxidation, assisted by the strong electron accepting ability of the isoalloxazine moiety in flavins. Probe 1 also exhibited high selectivity for f...
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The oxidation of alkyl and aryl aldehydes to their corresponding carboxylic acids has been achieved through the action of a biomimetic bridged flavin catalyst. The reaction uses readily available 35% aqueous hydrogen peroxide and is operationally simple. The oxidation is a green and sustainable reaction, obviating chlorinated solvents with minimal byproducts.
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An enzyme has been partially purified from brewer's yeast which catalyzes the reversible reaction between riboflavin phosphate and adenosine triphosphate (ATP) on the one hand and flavin-adenine dinucleotide (FAD) and inorganic pyrophosphate on the other in the presence of magnesium ions. ATP could not be replaced by adenosine diphosphate or adenosine-5-phosphate, and in the reverse reaction, i...
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The Claisen rearrangement and its applications to organic synthesis have been studied for a long time.l In recent years, this rearrangement has been applied in stereocontrolled natural product synthesis2 and asymmetric i n d ~ c t i o n . ~ The term "Claisen rearrangement", which originally denoted the rearrangement of allyl aryl ethers to 0or p-allylphenols, has now been extended to analogous ...
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ژورنال
عنوان ژورنال: Nature
سال: 2013
ISSN: 0028-0836,1476-4687
DOI: 10.1038/nature12643