Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction

doi:10.1021/acsomega.8b00852

CORC > 化学研究所 > 中国科学院化学研究所 > 胶体、界面与化学热力学实验室

	Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction
	Bhowmick, Sudipto 1; Zhang, Li 1; Ouyang, Guanghui 1; Liu, Minghua 1,2,3
刊名	ACS OMEGA
	2018-07-01
卷号	3 期号:7 页码:8329-8336
ISSN号	2470-1343
DOI	10.1021/acsomega.8b00852
英文摘要	Chiral self-assembly has drawn increasing interest in supramolecular chemistry. Here, we have designed amphiphilic L-Pro-L-Glu and L-Pro-D-Glu dipeptides and investigated their chiral self-assembly as well as asymmetric catalytic performance to disclose the synergistic effect of two stereogenic centers in the self-assembly and catalysis. It was found that both of the diastereomeric dipeptides can easily self-assemble into organogels with nanofibers. When these nanofibers were used as a catalyst for the asymmetric aldol reactions, enhanced enantioselectivity was obtained compared with their molecular state. Moreover, the L-L isomer assemblies showed higher enantioselectivity than the L-D isomer. It was revealed that both the supramolecular chirality of the nanofiber and the chiral catalytic site of L-proline played important roles in the asymmetric catalysis. In addition, the synergistic effect of two homochiral centers led to more efficient supramolecular catalysis that the L-L assemblies showed high yields (up to 97%), anti-diastereoselectivity (up to 99%), and excellent enantioselectivity (up to >99%).
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000440615900041
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/41919]
专题	化学研究所_胶体、界面与化学热力学实验室中国科学院化学研究所
通讯作者	Liu, Minghua
作者单位	1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, CAS Key Lab Colloid Interface & Chem Thermodynam, Zhongguancun Beiyijie 2, Beijing 100190, Peoples R China 2.Natl Ctr Nanosci & Technol, Zhongguancun Beiyitiao 11, Beijing 100190, Peoples R China 3.Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
推荐引用方式 GB/T 7714	Bhowmick, Sudipto,Zhang, Li,Ouyang, Guanghui,et al. Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction[J]. ACS OMEGA,2018,3(7):8329-8336.
APA	Bhowmick, Sudipto,Zhang, Li,Ouyang, Guanghui,&Liu, Minghua.(2018).Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction.ACS OMEGA,3(7),8329-8336.
MLA	Bhowmick, Sudipto,et al."Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction".ACS OMEGA 3.7(2018):8329-8336.