A Density Functional Theory Study on the Catalytic Mechanism of Hydroxycinnamoyl-CoA Hydratase-Lyase

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	A Density Functional Theory Study on the Catalytic Mechanism of Hydroxycinnamoyl-CoA Hydratase-Lyase
	Ma, Guangcai 1; Li, Yulin 2; Wei, Lixin 2; Liu, Yongjun 1,2; Liu, Chengbu 1
	2014-02-15
发表期刊	INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
ISSN	0020-7608
卷号	114 期号:4 页码:249-254
文章类型	Article
摘要	Hydroxycinnamoyl-CoA hydratase-lyase (HCHL), a particular member of the crotonase superfamily, catalyzes the bioconversion of feruloyl-CoA to the important flavor and fragrance compound vanillin. In this article, the catalytic mechanism of HCHL has been studied by using hybrid density functional theory method with simplified models. The calculated results reveal that the mechanism involves the hydration of the CC double bond of feruloyl-CoA and thence the cleavage of CC single bond of -hydroxythioester. The hydration step is a typical concerted process, whereas CC bond cleavage follows a concerted but asynchronous mechanism. The calculated energy barrier of hydration reaction is only slightly lower than that of cleavage process, implying both of two processes are rate limiting. By using three substrate analogs, the substrate specificity of HCHL was further examined. It is found that the p-hydroxyl group of aromatic ring is necessary for the catalytic reaction. (c) 2013 Wiley Periodicals, Inc.; Hydroxycinnamoyl-CoA hydratase-lyase (HCHL), a particular member of the crotonase superfamily, catalyzes the bioconversion of feruloyl-CoA to the important flavor and fragrance compound vanillin. In this article, the catalytic mechanism of HCHL has been studied by using hybrid density functional theory method with simplified models. The calculated results reveal that the mechanism involves the hydration of the CC double bond of feruloyl-CoA and thence the cleavage of CC single bond of -hydroxythioester. The hydration step is a typical concerted process, whereas CC bond cleavage follows a concerted but asynchronous mechanism. The calculated energy barrier of hydration reaction is only slightly lower than that of cleavage process, implying both of two processes are rate limiting. By using three substrate analogs, the substrate specificity of HCHL was further examined. It is found that the p-hydroxyl group of aromatic ring is necessary for the catalytic reaction. (c) 2013 Wiley Periodicals, Inc.
关键词	Hydroxycinnamoyl-coa Hydratase-lyase Density Functional Theory Method Catalytic Mechanism Substrate Specificity
WOS标题词	Science & Technology ; Physical Sciences
关键词[WOS]	1.8 ANGSTROM RESOLUTION ; FERULIC ACID ; CROTONASE SUPERFAMILY ; COENZYME-A ; PSEUDOMONAS-FLUORESCENS ; CRYSTAL-STRUCTURE ; ESCHERICHIA-COLI ; VANILLIN ; ENZYME ; THERMOCHEMISTRY
收录类别	SCI
语种	英语
WOS研究方向	Chemistry ; Mathematics ; Physics
WOS类目	Chemistry, Physical ; Mathematics, Interdisciplinary Applications ; Physics, Atomic, Molecular & Chemical
WOS记录号	WOS:000329509400002
引用统计	被引频次：5[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://210.75.249.4/handle/363003/4252
专题	中国科学院西北高原生物研究所
作者单位	1.Shandong Univ, Sch Chem & Chem Engn, Key Lab Theoret & Computat Chem Univ Shandong, Jinan 250100, Shandong, Peoples R China 2.Chinese Acad Sci, Northwest Inst Plateau Biol, Xining 810001, Qinghai, Peoples R China
推荐引用方式 GB/T 7714	Ma, Guangcai,Li, Yulin,Wei, Lixin,et al. A Density Functional Theory Study on the Catalytic Mechanism of Hydroxycinnamoyl-CoA Hydratase-Lyase[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2014,114(4):249-254.
APA	Ma, Guangcai,Li, Yulin,Wei, Lixin,Liu, Yongjun,&Liu, Chengbu.(2014).A Density Functional Theory Study on the Catalytic Mechanism of Hydroxycinnamoyl-CoA Hydratase-Lyase.INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,114(4),249-254.
MLA	Ma, Guangcai,et al."A Density Functional Theory Study on the Catalytic Mechanism of Hydroxycinnamoyl-CoA Hydratase-Lyase".INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY 114.4(2014):249-254.

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