Optically Active beta-Methyl-delta-Valerolactone: Biosynthesis and Polymerization

	Optically Active beta-Methyl-delta-Valerolactone: Biosynthesis and Polymerization
	Zhang, Chaoqun 1,2; Schneiderman, Deborah K.3; Cai, Tao 2,4; Tai, Yi-Shu 2; Fox, Kevin 2; Zhang, Kechun 2
刊名	ACS SUSTAINABLE CHEMISTRY & ENGINEERING
	2016-08-01
卷号	4 期号:8 页码:4396-4402
关键词	Biosynthesis Chemo-enzymatic pathways Enatntioselectivity Isotactic polymer Thermal properties
英文摘要	Chemo-enzymatic pathways were developed to prepare optically enriched (+)-beta-methyl-delta-valerolactone and (-)-beta-methyl-delta-valerolactone. Anhydromevalonolactone, synthesized by the acid-catalyzed dehydration of bioderived mevalonate, was transformed to (+)-beta-methyl-delta-valerolactone with 76% ee and 69% conversion using the mutant enoate reductase, YqjM(C26D, I69T). With the same substrate but a different enoate reductase (OYE2), we obtained the other enantiomer ((-)-beta-methyl-delta-valerolactone) with higher selectivity and yield (96% ee and a 92% conversion). The enzyme docking program LibDock was used to help explain the origin of the divergent enatntioselectivity of the two reductases, and complementary in vitro experiments were used to determine the turnover number and Michaelis constant for each. Finally, the effect of the enantiopurity of the beta-methyl-delta-valerolactone monomer on the properties of the corresponding polyester was investigated. Like atactic poly((+/-)-beta-methyl-delta-valerolactone), the isotactic polymer was determined to be amorphous with a low softening temperature (-52 degrees C).
WOS标题词	Science & Technology ; Physical Sciences ; Technology
类目[WOS]	Chemistry, Multidisciplinary ; Engineering, Chemical
研究领域[WOS]	Chemistry ; Engineering
关键词[WOS]	ALCOHOL-DEHYDROGENASE ; GAMMA-BUTYROLACTONES ; ENZYMATIC-SYNTHESIS ; LACTONES ; REDUCTION ; 2-BUTENOLIDES ; OXIDATIONS ; REDUCTASES ; SYSTEMS ; FAMILY
收录类别	SCI
语种	英语
WOS记录号	WOS:000380869800039
内容类型	期刊论文
源URL	[http://124.16.173.210/handle/834782/2917]
专题	天津工业生物技术研究所_总体研究部_期刊论文
作者单位	1.South China Agr Univ, Coll Mat & Energy, Guangzhou 510642, Guangdong, Peoples R China 2.Univ Minnesota, Dept Chem Engn & Mat Sci, Minneapolis, MN 55455 USA 3.Univ Minnesota, Dept Chem, 207 Pleasant St SE, Minneapolis, MN 55455 USA 4.Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin 300308, Peoples R China
推荐引用方式 GB/T 7714	Zhang, Chaoqun,Schneiderman, Deborah K.,Cai, Tao,et al. Optically Active beta-Methyl-delta-Valerolactone: Biosynthesis and Polymerization[J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING,2016,4(8):4396-4402.
APA	Zhang, Chaoqun,Schneiderman, Deborah K.,Cai, Tao,Tai, Yi-Shu,Fox, Kevin,&Zhang, Kechun.(2016).Optically Active beta-Methyl-delta-Valerolactone: Biosynthesis and Polymerization.ACS SUSTAINABLE CHEMISTRY & ENGINEERING,4(8),4396-4402.
MLA	Zhang, Chaoqun,et al."Optically Active beta-Methyl-delta-Valerolactone: Biosynthesis and Polymerization".ACS SUSTAINABLE CHEMISTRY & ENGINEERING 4.8(2016):4396-4402.