Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana
Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana
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连翘无细胞提取物对映选择性木脂素合成
DOI：
10.1271/bbb.58.230
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发表时间：
1994
期刊：
影响因子：
--
通讯作者：
M. Shimada
中科院分区：
文献类型：
--
作者：
T. Umezawa;H. Kuroda;Toshinari Isohata;T. Higuchi;M. Shimada
朝鲜连翘植物产生木脂素如（−）-开环异落叶松树脂酚和（+）-松脂醇。在NADPH和H2 O2存在下，植物的无细胞提取物催化[9，9- 2 H2，OC 2 H3]松柏醇对映选择性形成（−）-[2 H10]开环异落叶松树脂酚。另一方面，发现从酶促反应产物中分离的[2 H10]lariciresinosl主要由非天然的（-）-对映异构体组成[88%对映异构体过量（e.e.）]。这些木脂素形成的立体选择性可以至少部分地通过以下发现来解释：酶系统也催化（+）-落叶松树脂酚而不是其（-）-对映体立体选择性还原为（-）-开环异落叶松树脂酚。
The Forsythia koreana plant produces such lignans as ( − )-secoisolariciresinol, and ( + )-pinoresinol. Cell-free extracts from the plant catalyzed the enantioselective formation of ( − )-[2H10]secoisolariciresinol from [9, 9-2H2, OC2H3]coniferyl alcohol in the presence of NADPH and H2 O2. On the other hand, [2H10]lariciresinosl isolated from the enzymatic reaction products was found to be predominantly composed of the unnatural ( − )-enantiomer [88% enantiomer excess (e.e.)]. The stereoselectivity for the formation of these lignans can be explained, at least in part, by the finding that the enzyme system also catalyzed the stereoselective reduction of ( + )-lariciresinol, but not its ( − )-enantiomer, to ( − )-secoisolariciresinol.