Photochemical and enzymatic SET promoted C-C bond cleavage reactions of lignin beta-1 model compounds containing varying number of methoxy substituents on their arene rings

Title
Photochemical and enzymatic SET promoted C-C bond cleavage reactions of lignin beta-1 model compounds containing varying number of methoxy substituents on their arene rings
Author(s)
조대원임숙현이우솔김영일손영구김철희[김철희]김은애[김은애]John A Latham[John A Latham]Debra Dunaway-Mariano[Debra Dunaway-Mariano]Patrick S Mariano[Patrick S Mariano]
Keywords
PEROXIDASE-CATALYZED OXIDATION; OXYGEN-MEDIATED DEGRADATION; ARYL ETHER TYPE; PHANEROCHAETE-CHRYSOSPORIUM; ELECTRON-TRANSFER; SINGLET-OXYGEN; VERATRYL ALCOHOL; 3,4-DIMETHOXYBENZYL ALCOHOL; LIGNOCELLULOSIC BIOMASS; FRAGMENTATION REACTIONS
Issue Date
201506
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON, v.71, no.24, pp.4236 - 4247
Abstract
In the current study, 1,2-diarylpropan-1,3-diols, containing varying numbers of methoxy substituents that mimic beta-1 type units in lignins, were prepared and subjected to photochemical and enzymatic SET oxidative C-C bond cleavage reactions to explore how product distributions and reactivity profiles depend on the numbers and positions of arene ring methoxy-substituents. For this purpose, product distributions of SET-promoted photochemical reactions of the beta-1 model compounds and the characteristics of lignin peroxidase catalyzed bond cleavage reactions of these substances were explored. The results show that both the photochemical and enzymatic reactions, which are known to occur by initial SET to form arylpropanoid cation radicals, generate predominantly aldehydes and beta-hydroxyketones through cation radical C1-C2 bond cleavage pathways. In addition, analysis of the relative quantum efficiencies of the SET photochemical processes shows that they do not depend greatly on the numbers and positions of arene ring methoxy substituents of the beta-1 model compounds. (C) 2015 Elsevier Ltd. All rights reserved.
URI
http://hdl.handle.net/YU.REPOSITORY/32077http://dx.doi.org/10.1016/j.tet.2015.04.077
ISSN
0040-4020
Appears in Collections:
이과대학 > 화학생화학부 > Articles
문과대학 > 중국언어문화학과 > Articles
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