Surface-Induced Diastereomeric Complex Formation of a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition and Preferential Adsorption

doi:10.1021/ja402914m

	Surface-Induced Diastereomeric Complex Formation of a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition and Preferential Adsorption
	Guo, Zongxia1,4 ; De Cat, Inge 1; Van Averbeke, Bernard 3; Ghijsens, Elke 1; Lin, Jianbin 2; Xu, Hong 1; Wang, Guojie 1; Hoeben, Freek J. M.2; Tomovic, Zeljko 2; Lazzaroni, Roberto 3; Beljonne, David 3; Meijer, E. W.2; Schenning, Albertus P. H. J.2; De Feyter, Steven 1
	2013-07-03
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷号	135 期号:26 页码:9811-9819
摘要	With the aim of achieving surface-mediated enantioselective adsorption, the self-assembly of chiral oligo(p-phenylenevinylene) (OPV3T) with nucleosides is investigated at the liquid/solid interface by means of scanning tunneling microscopy and molecular modeling. OPV3T enantiomers form mirror related hexameric rosette patterns. The DNA nucleoside, thymidine, does not self-assemble into stable adlayers but coadsorbs with OPV3T on the surface, leading to a pattern transformation of OPV3T from rosettes to dimers, and a change in chiral expression as well Diastereoselective recognition between OPV3T and thymidine enantiomers can be used to resolve thymidine enantiomers at an achiral surface with an OPV3T enantiomer as the resolving agent. The impact of molar ratio and concentration on the self-assembly and chiral resolution is systematically investigated Because there is no interaction between OPV3T and thymidine in solution, the liquid/solid interface acts as the platform for the chiral resolution of thymidine enantiomers.
文章类型	Article
WOS标题词	Science & Technology ; Physical Sciences
DOI	10.1021/ja402914m
关键词[WOS]	SCANNING-TUNNELING-MICROSCOPY ; SPONTANEOUS RESOLUTION ; 2-DIMENSIONAL CRYSTALS ; STEREOGENIC CENTERS ; CHIRAL SEPARATION ; ORGANIC-MOLECULES ; ASSEMBLIES ; ACID ; MONOLAYERS ; HOMOCHIRALITY
收录类别	SCI
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000321541800043
引用统计
文献类型	期刊论文
条目标识符	http://ir.qibebt.ac.cn/handle/337004/6003
专题	生物基及仿生高分子材料团队（过去）
作者单位	1.Katholieke Univ Leuven, Dept Chem, Div Mol Imaging & Photon, B-3001 Louvain, Belgium 2.Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands 3.Univ Mons UMONS, Serv Chim Mat Nouveaux, B-7000 Mons, Belgium 4.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Peoples R China
推荐引用方式 GB/T 7714	Guo, Zongxia,De Cat, Inge,Van Averbeke, Bernard,et al. Surface-Induced Diastereomeric Complex Formation of a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition and Preferential Adsorption[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2013,135(26):9811-9819.
APA	Guo, Zongxia.,De Cat, Inge.,Van Averbeke, Bernard.,Ghijsens, Elke.,Lin, Jianbin.,...&De Feyter, Steven.(2013).Surface-Induced Diastereomeric Complex Formation of a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition and Preferential Adsorption.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,135(26),9811-9819.
MLA	Guo, Zongxia,et al."Surface-Induced Diastereomeric Complex Formation of a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition and Preferential Adsorption".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 135.26(2013):9811-9819.