Optical Resolution of the Water-Soluble Ti4(embonate)6 Cages for Enantioselective Recognition of Chiral Drugs

被引：55

作者：

He, Yan-Ping ^{[1
]}

Yuan, Lv-Bing ^{[1
]}

Song, Jin-Shuai ^{[1
]}

Chen, Guang-Hui ^{[1
]}

Ling, Qipu ^{[1
]}

Li, Chunsen ^{[1
]}

Zhang, Lei ^{[1
]}

Zhang, Jian ^{[1
]}

机构：

[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

来源：

CHEMISTRY OF MATERIALS | 2018年 / 30卷 / 21期

关键词：

METAL-ORGANIC POLYHEDRA; COORDINATION CAGES; STEREOCHEMISTRY; TETRAHEDRON; COMPLEXES; MOLECULES; VALENCE; DESIGN; HOST;

D O I：

10.1021/acs.chemmater.8b03174

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Synergetic optical resolution and chiral amplification of tetrahedral Ti4L6 cages by enantiopure coordination cations have been realized in this work. Anionic Delta Delta Delta Delta-[Ti4L6] and Lambda Lambda Lambda Lambda-[Ti4L6] cages (L = embonate) have been completely resolved by enantiopure Lambda-[Mn(1R,2R-DCH)(3)] and Delta-[Mn(1S,2S-DCH)(3)] cations, respectively. Accordingly, two homochiral compounds (PTC-108(Delta) and PTC-108(Lambda)) with three-dimensional supramolecular architectures were formed, containing larger diamondoid cages. Such an unusual resolution process clearly shows the stepwise transfer of homochirality from an enantiopure molecule to a resolved hydrogen-bonding aggregation and a final homochiral framework. Moreover, the separated homochiral Ti4L6 cage presents enantioselective recognition toward chiral organic and pharmaceutical molecules. This work opens a novel resolution-dependent homochiral framework construction approach, and it also takes the homochiral tetrahedral Ti4L6 cages with high solubility and stability into promising enantioselective application.

引用

页码：7769 / 7775

页数：7

共 45 条

[1] Chiral confined space:: Induction of stereochemistry in a M4L4 metallosupramolecular container [J].

Albrecht, Markus ;

Burk, Simon ;

Weis, Patrick .

SYNTHESIS-STUTTGART, 2008, (18) :2963-2967

[2] Sign inversion of circularly polarized luminescence by geometry manipulation of four naphthalene units introduced into a tartaric acid scaffold [J].

Amako, Tomoyuki ;

Nakabayashi, Kazuki ;

Mori, Tadashi ;

Inoue, Yoshihisa ;

Fujiki, Michiya ;

Imai, Yoshitane .

CHEMICAL COMMUNICATIONS, 2014, 50 (85) :12836-12839

[3] Diastereoselective formation and optical activity of an M4L6 cage complex [J].

Argent, SP ;

Riis-Johannessen, T ;

Jeffery, JC ;

Harding, LP ;

Ward, MD .

CHEMICAL COMMUNICATIONS, 2005, (37) :4647-4649

[4] A Pd24 Pregnant Molecular Nanoball: Self-Templated Stellation by Precise Mapping of Coordination Sites [J].

Bhat, Imtiyaz Ahmad ;

Samanta, Dipak ;

Mukherjee, Partha Sarathi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) :9497-9502

[5] Generation of a Dynamic System of Three-Dimensional Tetrahedral Polycatenanes [J].

Black, Samuel P. ;

Stefankiewicz, Artur R. ;

Smulders, Maarten M. J. ;

Sattler, Dominik ;

Schalley, Christoph A. ;

Nitschke, Jonathan R. ;

Sanders, Jeremy K. M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) :5749-5752

[6] Enantiopure Water-Soluble [Fe4L6] Cages: Host-Guest Chemistry and Catalytic Activity [J].

Bolliger, Jeanne L. ;

Belenguer, Ana M. ;

Nitschke, Jonathan R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) :7958-7962

[7] Enantioselective Catalysis of the Aza-Cope Rearrangement by a Chiral Supramolecular Assembly [J].

Brown, Casey J. ;

Bergman, Robert G. ;

Raymond, Kenneth N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (48) :17530-17531

[8] Stereochemistry in Subcomponent Self-Assembly [J].

Castilla, Ana M. ;

Ramsay, William J. ;

Nitschke, Jonathan R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (07) :2063-2073

[9] High-Fidelity Stereochemical Memory in a Fe4IIL4 Tetrahedral Capsule [J].

Castilla, Ana M. ;

Ousaka, Naoki ;

Bilbeisi, Rana A. ;

Valeri, Elisa ;

Ronson, Tanya K. ;

Nitschke, Jonathan R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (47) :17999-18006

[10]

Caulder DL, 1998, ANGEW CHEM INT EDIT, V37, P1840, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1840::AID-ANIE1840>3.0.CO

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