An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols

被引:126
|
作者
Pickel, Benjamin [2 ]
Constantin, Mihaela-Anca [1 ]
Pfannstiel, Jens [3 ,4 ]
Conrad, Juergen [1 ]
Beifuss, Uwe [1 ]
Schaller, Andreas [2 ]
机构
[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany
[2] Univ Hohenheim, Inst Physiol & Biotechnol Pflanzen, D-70599 Stuttgart, Germany
[3] Univ Hohenheim, Life Sci Ctr, D-70593 Stuttgart, Germany
[4] Univ Hohenheim, Inst Physiol, D-70593 Stuttgart, Germany
关键词
arabidopsis; dirigent proteins; enantioselectivity; lignans; phenol couplings; SHIRAIA-BAMBUSICOLA; BIOSYNTHESIS; EXPRESSION; VIOXANTHIN;
D O I
10.1002/anie.200904622
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(+)- or (-)-plnoreslnol: that Is the question. Which of the two enantiomeric lignans is formed during laccasecatalyzed phenol coupling of (E)-coniferyl alcohol (1) depends on the dirigent protein. In the presence of the first enantiocomplementary dirigent protein AtDIR6, (-)-2 is formed (78 % ee). Preferential formation of (+)-2 is observed in the presence of the dirigent protein FiDIR1, whereas only racemic 2 is formed in the absence of dirigent proteins © 2010 Wiley-VCHVerlag GmbH & Co. KCaA, Weinheim.
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页码:202 / 204
页数:3
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