期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 8, 页码 2840-2852出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200253v
关键词
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资金
- U.S. Department of Energy [20080001DR]
- National Research Foundation of Korea [2009-0072585]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0946690] Funding Source: National Science Foundation
- National Research Foundation of Korea [2009-0072585] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
New types of tetrameric lignin model compounds, which contain the common beta-O-4 and,beta-1 structural subunits found in natural lignins, have been prepared and carbon carbon bond fragmentation reactions of their cation radicals, formed by photochemical (9,10-dicyanoanthracene) and enzymatic (lignin peroxidase) SET-promoted methods, have been explored. The results show that cation radical intermediates generated from the tetrameric model compounds undergo highly regioselective C C bond cleavage in their beta-1 subunits. The outcomes of these processes suggest that, independent of positive charge and odd-electron distributions, cation radicals of lignins formed by SET to excited states of sensitizers or heme-iron centers in enzymes degrade selectively through bond cleavage reactions in beta-1 vs beta-O-4 moieties. In addition, the findings made in the enzymatic studies demonstrate that the sterically large tetrameric lignin model compounds undergo lignin peroxidase-catalyzed cleavage via a mechanism involving preliminary, formation of an enzyme substrate complex.
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