与II类二萜环化酶呈顺式或反式。
cis or trans with class II diterpene cyclases.
作者信息
Jia Meirong, Peters Reuben J
机构信息
Roy J. Carver Department of Biochemistry, Biophysics & Molecular Biology, Iowa State University, Ames, IA 50010, USA.
出版信息
Org Biomol Chem. 2017 Apr 11;15(15):3158-3160. doi: 10.1039/c7ob00510e.
Abstract
Isoprenoid precursors readily undergo (poly)cyclization in electrophilic reaction cascades, presumably as internal addition of the carbon-carbon double-bonds from neighboring isoprenyl repeats readily forms relatively stable cyclohexyl tertiary carbocation intermediates. This hypothesis is agnostic regarding alkene configuration (i.e., Z or E). Consistent with this, here it is shown that certain class II diterpene cyclases, which normally convert (E,E,E)-geranylgeranyl diphosphate to 13E-trans-decalin bicycles, will also act upon (Z,Z,Z)-nerylneryl diphosphate, producing novel 13Z-cis-decalin bicycles instead.
摘要
类异戊二烯前体在亲电反应级联中很容易发生（多）环化，据推测，相邻异戊烯基重复单元的碳 - 碳双键的分子内加成很容易形成相对稳定的环己基叔碳正离子中间体。该假设与烯烃构型（即Z型或E型）无关。与此一致的是，此处表明某些II类二萜环化酶，通常将（E,E,E）-香叶基香叶基二磷酸转化为13E-反式十氢化萘双环结构，也会作用于（Z,Z,Z）-橙花叔基二磷酸，反而产生新型的13Z-顺式十氢化萘双环结构。
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