TRICHODIENE SYNTHASE - SYNERGISTIC INHIBITION BY INORGANIC PYROPHOSPHATE AND AZA ANALOGS OF THE BISABOLYL CATION
TRICHODIENE SYNTHASE - SYNERGISTIC INHIBITION BY INORGANIC PYROPHOSPHATE AND AZA ANALOGS OF THE BISABOLYL CATION
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DOI：
10.1021/jo00038a040
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发表时间：
1992-06-05
影响因子：
3.6
通讯作者：
HOHN, TM
中科院分区：
文献类型：
--
作者：
CANE, DE;YANG, GH;HOHN, TM
一系列的红没药基和α-萜品基阳离子的氮杂类似物作为倍半萜环化酶，β-二烯合酶的抑制剂进行了测试。当单独孵育时，（R）-和（S）-16和（R）-和（S）-13以及三甲胺仅为弱抑制剂。在无机焦磷酸盐，本身是一个已知的竞争性抑制剂的β-二烯合酶的存在下，所有五个胺表现出很强的合作竞争性抑制与增强因子估计为10-40。表观诱导抑制常数α-K（j）在从三甲胺到单萜类似物13的过程中降低，并且对于倍半萜类似物16最强，表明静电和疏水相互作用在每个中间类似物的结合中都是重要的。环化酶表现出很小的歧视，但是，每个抑制剂的个别对映体之间。
A series of aza analogs of the bisabolyl and alpha-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase. Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone. In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40. The apparent induced inhibition constant alpha-K(j) decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog. The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.