Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate.
Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate.
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DOI：
10.1021/bi201827a
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发表时间：
2012-04-10
期刊：
影响因子：
2.9
通讯作者：
Christianson, David W.
中科院分区：
文献类型：
--
作者：
Koeksal, Mustafa;Chou, Wayne K. W.;Cane, David E.;Christianson, David W.
天蓝色链霉菌（Streptomycescoelicolor）A3（2）的2-甲基异山梨醇合酶（MIBS）与底物类似物香叶基硫代二磷酸和2-氟香叶基二磷酸的复合物的晶体结构分别在1.80和1.95 μ m的分辨率下得到测定。这种萜类环化酶催化天然存在的非典型C-甲基化类异戊二烯底物2-甲基香叶基二磷酸的环化，以形成双环产物2-甲基异戊烯，一种具有泥土霉味的挥发性C11高萜醇。虽然MIBS采用I类萜类化合物环化酶的三级结构，但其二聚体四级结构不同于先前在来自植物和真菌的二聚体萜类化合物环化酶中观察到的结构。然而，MIBS的四级结构在某些方面与二聚法呢基二磷酸合酶相似，而法呢基二磷酸合酶不是环化酶。与底物类似物复合的MIBS的结构提供了关于MIBS的催化机制与（+）-藜芦基二磷酸合酶和内切-小茴香酚合酶的机制的差异的见解，所述（+）-藜芦基二磷酸合酶和内切-小茴香酚合酶是将香叶基二磷酸转化为具有密切相关的双环藜芦基骨架但具有不同结构和立体化学的产物的植物环化酶。
The crystal structure of 2-methylisoborneol synthase (MIBS) from Streptomyces coelicolor A3(2) has been determined in complex with substrate analogues geranyl-S-thiolodiphosphate and 2-fluorogeranyl diphosphate at 1.80 Å and 1.95 Å resolution, respectively. This terpenoid cyclase catalyzes the cyclization of the naturally-occuring, non-canonical C-methylated isoprenoid substrate, 2-methylgeranyl diphosphate, to form the bicyclic product 2-methylisoborneol, a volatile C11 homoterpene alcohol with an earthy, musty odor. While MIBS adopts the tertiary structure of a class I terpenoid cyclase, its dimeric quaternary structure differs from that previously observed in dimeric terpenoid cyclases from plants and fungi. The quaternary structure of MIBS is nonetheless similar in some respects to that of dimeric farnesyl diphosphate synthase, which is not a cyclase. The structures of MIBS complexed with substrate analogues provide insights regarding differences in the catalytic mechanism of MIBS and the mechanisms of (+)-bornyl diphosphate synthase and endo-fenchol synthase, plant cyclases that convert geranyl diphosphate into products with closely related bicyclic bornyl skeletons, but distinct structures and stereochemistries.
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DOI：
10.1351/pac-con-09-09-37
发表时间：
2010
期刊：
Pure and applied chemistry. Chimie pure et appliquee
影响因子：
--
作者：
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通讯作者：
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影响因子：
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发表时间：
2010-02
期刊：
Acta crystallographica. Section D, Biological crystallography
影响因子：
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通讯作者：
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DOI：
10.1107/s0907444998003254
发表时间：
1998-09-01
期刊：
ACTA CRYSTALLOGRAPHICA SECTION D-BIOLOGICAL CRYSTALLOGRAPHY
影响因子：
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作者：
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通讯作者：
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