Baciocchi, Enrico published the artcileLignin peroxidase-catalyzed oxidation of nonphenolic trimeric lignin model compounds: Fragmentation reactions in the intermediate radical cations, Application In Synthesis of 183303-74-4, the publication is Journal of Organic Chemistry (2003), 68(23), 9061-9069, database is CAplus and MEDLINE.
The H2O2-promoted oxidations of the two nonphenolic β-O-aryl lignin model trimers 1 and 2, catalyzed by lignin peroxidase (LiP) at pH = 3.5, have been studied. The results have been compared with those obtained in the oxidation of 1 and 2 with the genuine one-electron oxidant potassium 12-tungstocobalt(III)ate. These models present a different substitution pattern of the three aromatic rings, and by one-electron oxidation, they form radical cations with the pos. charge, which is localized in the dialkoxylated ring as also evidenced by a pulse radiolysis study. Both the oxidations with the enzymic and with the chem. systems lead to the formation of products deriving from the cleavage of C-C and C-H bonds in a β position with respect to the radical cation with the charge residing in the dialkoxylated ring (3,4-dimethoxybenzaldehyde (5) and a trimeric ketone 6 in the oxidation of 1 and a dimeric aldehyde 8 and a trimeric ketone 9 in the oxidation of 2). These products are accompanied by a dimeric aldehyde 7 in the oxidation of 1 and 4-methoxybenzaldehyde (10) in the oxidation of 2. The unexpected formation of these two products has been explained by suggesting that 1â? and 2â? can also undergo an intramol. electron transfer leading to the radical cations 1aâ? and 2aâ? with the charge residing in a monoalkoxylated ring. The fast cleavage of a C-C bond β to this ring, leading to 7 from 1â? and to 10 from 2â?, is the driving force of the endoergonic electron transfer. A kinetic steady-state investigation of the LiP-catalyzed oxidation of the trimer 2, the dimeric model 1-(3,4-dimethoxyphenyl)-2-phenoxy-1-ethanol (4), and 3,4-dimethoxybenzyl alc. (3) has indicated that the turnover number (kcat) and the affinity for the enzyme decrease significantly by increasing the size of the model compound In contrast, the three substrates exhibited a very similar reactivity toward a chem. oxidant [CoIIIW]. This suggests a size-dependent interaction of the enzyme with the substrate which may influence the efficiency of the electron transfer.
Journal of Organic Chemistry published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, Application In Synthesis of 183303-74-4.
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