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Self-assembly of Novel Hetero[3]rotaxane,[2]Rotaxanes and [2]catenane

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Chinese Journal of Chemistry 2003年第7期21卷 739-745页

作者：张未星范翠琴屠波赵新蒋锡夔黎占亭 College of Materials Scicnce and Chemical Engineering Zhejiang Uinversity Hangzhou Zhejiang 310027China Department of Chemistry Fudan UniversityShanghai 200433China Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

One linear template 13 and one cyclophane template 15, both incorporating two electron rich 1,4-dialkoxybenzene units and one diamide unit, have been synthesized. By utilizing donor-acceptor interaction and/or intermolecular hydrogen bonding assembling principles, one novel hetero[3]rotaxane 22·4Cl, possessing one neutral and one tetracationic ring components, has been synthesized from 13, through neutral [2]rotaxane 21 as intermediate. With 15 as template, tetracationic [2]catenane 23·4PF6 was assembled by using donor-acceptor interaction, but no neutral [2]rotaxane could be obtained under the typical conditions of hydrogen bonding assembling principle. The interlocked supramolecular compounds have been characterized and their spectral properties are investigated.

关键词： self-assembly rotaxane catenane

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Synthesis and Characterization of Two [2]catenanes Based on Phenylene-diacetylene Crown Ethers

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Chemical Research in Chinese Universities 2013年第6期29卷 1094-1097页

作者： CHEN Mu-juan ZHOU Song-gen LI Mei LEI Chun-yan XIAO Rui JIANG La-sheng School of Chemistry and Environment South China Normal University Guangzhou 510006 P.R.China

Two charged donor-acceptor [2]catenanes were synthesized by the cyclization of the π-acceptor 1,1 ＇-[1, 4-phenylenebis-（methylene）]bis（4,4＇-bipyridinium）bis（hexafluorophosphate）（2） and bis（bromomethyl）benzene with the templates of the π-donor phenylene-diacetylene crown ethers la and lb in the yields of 31%, 35%, respectively. The mass spectra, 1H and 13C NMR spectra confirm that the phenylene-diacetylene crown ethers, with a nonaromatic ~r-system, successfully template the cyclization of CBPQT4＋. The X-ray crystallography analysis shows that the CBPQT4＋ ring encircles around the phenylene motif of the crown ethers, leaving the 1,3-butadiyne fragment out of the cavity of CBPQT4＋ ring. The mechanically interlocked structure of [2]catenanes was stabilized by the cooperative effects of π-stacking and hydrogen bonding interactions.

关键词： catenane Crystal structure Crown ether

Active Template Synthesis of Protein[n]catenanes Using Engineered Peptide–Peptide Ligation Tools

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CCS Chemistry 2024年第2期6卷 377-389页

作者： Fan Zhang Yajie Liu Yu Shao Wen-Bin Zhang Beijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of EducationCenter for Soft Matter Science and EngineeringCollege of Chemistry and Molecular EngineeringPeking UniversityBeijing 100871 Beijing Academy of Artificial Intelligence Beijing 100084

The expansion of protein topological diversity requires new and efficient synthetic ***,we report the second and third generations of the SpyStapler-mediated SpyTag/BDTag ligation system for the efficient synthesis of 4-arm star proteins and the repurposing of the third generation as an active template to enable the synthesis of higher-order protein[n]catenanes(n=3,4,and 5).SpyStapler003 has a higher affinity to its cognate SpyTag and BDTag reactive pairs relative to the original ***,it can overcome much more profound steric hindrance in protein ligation and improve the efficiency of the resulting active template tool to facilitate the construction of radial protein[n]*** proteins of interest,such as dihydrofolate reductase and the nanobody KN035,can be modularly incorporated into the[n]catenanes with intact *** of passive and active template strategies gives rise to linear protein[4]catenanes,which further expands the current topological ***,higher-order protein catenation not only leads to enhanced thermal stability and proteolytic resistance but also higher affinity of the nanobody via multivalent *** study provides tools useful for bioconjugation and new topological protein scaffolds for the multivalent display of enzymes and antibodies.

关键词： SpyTag SpyCatcher catenane topology active template ligation

Topology: a unique dimension in protein engineering

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Science China Chemistry 2018年第1期61卷 3-16页

作者： Lianjie Xu Wen-Bin Zhang Key Laboratory of Polymer Chemistry & Physics of Ministry of Education Center for Soft Matter Science and EngineeringCollege of Chemistry and Molecular Engineering Peking University

Controlling protein topology has been a long standing challenge to go beyond their linear configuration defined by the translation mechanism of cellular machinery. In this mini-review, we focus on the topological diversity in proteins and review the major categories of protein topologies known to date, including branched/star proteins, circular proteins, lasso proteins, knotted proteins, and protein catenanes. The discovery of these topologically complex natural proteins and their synthetic pathways, the rational design and recombinant synthesis of artificial topological proteins and their biophysical studies, are summarized and discussed with regard to their general features and broad implications. The complexity of protein topology is recognized and the routes to diverse protein topologies are illustrated. We believe that topology engineering is an important way to modify protein properties without altemating their native sequences and shall bring in valuable dynamic features central to the creation of artificial protein machinery.

关键词： protein topology protein engineering catenane rotaxane knot lasso peptide

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Rational Design and Cellular Synthesis of Proteins with Unconventional Chemical Topology

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Chinese Journal of Chemistry 2023年第21期41卷 2873-2880页

作者： Tianzuo Li Fan Zhang Jing Fang Yajie Liu Wen-Bin Zhang Beijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry&Physics of Ministry of EducationCenter for Soft Matter Science and EngineeringCollege of Chemistry and Molecular EngineeringPeking UniversityBeijing100871 China Beijing Academy of Artificial Intelligence Beijing100084 China

Chemical topology refers to the three-dimensional arrangement(i.e.,connectivity and spatial relationship)of a molecule's constituent atoms and *** molecular mechanism for translation defines the linear configuration of all nascent *** protein topology arises only upon post-translational processing events and often imparts functional benefits such as enhanced stability,making topology a unique dimension for protein *** the assembly-reaction synergy,our group has developed several methods for the effective and convenient cellular synthesis of a variety of topological proteins,such as lasso proteins,protein rotaxanes,and protein *** work opens the access to new protein classes and paves the road toward illustrating the topological effects on structure-function relationship of proteins,which lays solid foundation for exploring topological proteins’practical application.

关键词： Active template catenane Cellular synthesis Chemical topology Lasso protein Protein engineering

Architecture of Platonic and Archimedean polyhedral links

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Science China Chemistry 2008年第1期51卷 13-18页

作者： QIU WenYuan ZHAI XinDong QIU YuanYuan Department of Chemistry State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou 730000China Faculty of Arts and Social Sciences The National University of SingaporeSG 117570Singapore

A new methodology for understanding the construction of polyhedral links has been developed on the basis of the Platonic and Archimedean solids by using our method of the ‘three-cross-curve and dou- ble-twist-line covering’. There are five classes of polyhedral links that can be explored: the tetrahedral and truncated tetrahedral links; the hexahedral and truncated hexahedral links; the dodecahedral and truncated dodecahedral links; the truncated octahedral and icosahedral links. Our results show that the tetrahedral and truncated tetrahedral links have T symmetry; the hexahedral and truncated hexahedral links, as well as the truncated octahedral links, O symmetry; the dodecahedral and truncated dodeca- hedral links, as well as the truncated icosahedral links, I symmetry, respectively. This study provides further insight into the molecular design, as well as theoretical characterization, of the DNA and protein catenanes.

关键词： knot theory polyhedron truncated polyhedron polyhedral link DNA catenane protein catenane

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Toward Selective Synthesis of Protein Olympiadanes via Orthogonal Active Templates in One Step

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CCS Chemistry 2024年第4期6卷 1047-1059页

作者： Fan Zhang Yajie Liu Xiao-Di Da Wen-Bin Zhang Beijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of EducationCenter for Soft Matter Science and EngineeringCollege of Chemistry and Molecular EngineeringPeking UniversityBeijing100871 Beijing Academy of Artificial Intelligence Beijing 100084

Unlike small molecules,the topological complexity of macromolecules remains largely unexplored due to the huge synthetic ***,we report the development of orthogonal active templates for concise and selective synthesis of protein[n]heterocatenanes toward protein *** active template(AT-Snoop)was first developed based on the isopeptide-bond-forming RrgA domain with comparable efficiency and excellent orthogonality to the previously reported active template(AT-Spy)based on the CnaB2 *** combination facilitated the selective synthesis of protein[n]catenanes from multiple components in one step and the resulting structures were verified by sodium dodecyl sulfate-polyacrylamide gel electrophoresis,size exclusion chromatography,liquid chromatography-mass spectrometry,and proteolytic digestion *** results offered a promising solution to tackling the daunting challenge of precision synthesis of protein olympiadane with five distinct ring *** only did the success provide new tools for proteintopology engin eering but alsospurred and fueled the future exploitation of topology-related functional benefits in protein science.

关键词： catenane topology active template SnoopTag SnoopCatcher SpyTag SpyCatcher

Catenated Cages Mediated by Enthalpic Reaction Intermediates

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CCS Chemistry 2021年第7期3卷 1838-1850页

作者： Shijun Xu Pan Li Zi-Ying Li Chunyang Yu Xiaoyun Liu Zhiqiang Liu Shaodong Zhang Key Laboratory of Specially Functional Polymeric Materials and Related Technology Ministry of EducationEast China University of Science and TechnologyShanghai 200237 School of Chemistry and Chemical Engineering Frontiers Science Center for Transformative MoleculesShanghai Key Laboratory of Electrical Insulation and Thermal AgingShanghai Jiao Tong UniversityShanghai 200240 The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals Zhejiang University of TechnologyHangzhou 310014

Catenated cages are generally considered thermodynamically more stable than their constituent monomeric ***,the catenation mechanism is yet to be elucidated;it would require systematic investigation into the structural effects of the building blocks,their enthalpic and entropic contributions,and the effect of *** inspecting these factors,we rationalized some design principles for the efficient construction of catenated cages.

关键词： cage catenane enthalpic intermediate interlocked cages supramolecular chemistry

Cellular Synthesis of Topological Proteins

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Cellular Synthesis of Topological Proteins