1407183-51-0Relevant articles and documents
Enantioselective Diels–Alder reactions with left-handed G-quadruplex DNA-based catalysts
Chen, Kun,He, Zhiyong,Xiong, Wei,Wang, Chun-Jiang,Zhou, Xiang
, p. 1701 - 1704 (2021)
Since the discovery of left-handed G-quadruplex (L-G4) structure formed by natural DNA, there has been a growing interest in its potential functions. This study utilised it to catalyse enantioselective Diels-Alder reactions, considering its different opti
Enantioselective Diels-Alder reactions using a G-triplex DNA-based catalyst
Xu, Xiaowei,Mao, Wuxiang,Lin, Feng,Hu, Jianlin,He, Zhiyong,Weng, Xiaocheng,Wang, Chun-Jiang,Zhou, Xiang
, p. 16 - 18 (2016)
In this study, it was found that the G-triplex DNA could be used as an enantioselective catalyst without further addition of ligands in Diels-Alder reactions when coordinated with copper ions, for the first time. The efficiency and selectivity of the cata
N, N ′-Dioxide/nickel(II)-catalyzed asymmetric Diels-Alder reaction of cyclopentadiene with 2,3-dioxopyrrolidines and 2-alkenoyl pyridines
Lu, Yan,Zhou, Yuhang,Lin, Lili,Zheng, Haifeng,Fu, Kai,Liu, Xiaohua,Feng, Xiaoming
, p. 8255 - 8258 (2016)
A chiral N,N′-dioxide/Ni(OTf)2 complex-catalyzed asymmetric Diels-Alder reaction of cyclopentadiene with 2,3-dioxopyrrolidines and 2-alkenoyl pyridines has been achieved. The corresponding chiral bridged compounds were obtained in high yields with excellent dr and ee values (up to 97% yield, 95: 5 dr and 97% ee).
Enantioselective Catalysis by Using Short, Structurally Defined DNA Hairpins as Scaffold for Hybrid Catalysts
Marek, Jasmin J.,Singh, Raghvendra P.,Heuer, Andreas,Hennecke, Ulrich
, p. 6004 - 6008 (2017)
A new type of DNA metal complex hybrid catalyst, which is based on single-stranded DNA oligonucleotides, is described. It was shown that oligonucleotides as short as 14 nucleotides that fold into hairpin structures are suitable as nucleic acid components for DNA hybrid catalysts. With these catalysts, excellent enantioinduction in asymmetric Diels–Alder reactions with selectivity values as high as 96 % enantiomeric excess (ee) can be achieved. Molecular dynamics simulations indicate that a rather flexible loop combined with a rigid stem region provides DNA scaffolds with these high selectivity values.
An Efficient Cyclic Di-AMP Based Artificial Metalloribozyme for Enantioselective Diels–Alder Reactions
Qi, Qianqian,Lv, Shuting,Hao, Min,Dong, Xingchen,Gu, Youkun,Wu, Peizhe,Zhang, Wenyue,Chen, Yashao,Wang, Changhao
, p. 4417 - 4424 (2020/06/17)
The diverse structures of nucleic acids as scaffolds have brought the significant advancement for DNA-based enantioselective catalysis, yet RNA-based enantioselective catalysis is lacking investigation. Herein, we report a small, natural RNA of cyclic di-AMP (c-di-AMP) and Cu2+ ions assemble into an artificial metalloribozyme (c-di-AMP·Cu2+), that could effectively catalyze the enantioselective Diels–Alder reactions with up to 80 percent ee. The enantioselective catalytic performance of c-di-AMP·Cu2+ has been studied by thorough investigations of different metal cofactors, c-di-AMP/Cu2+ molar ratios, additives, buffers and c-di-AMP analogues. In addition, the assembly of c-di-AMP·Cu2+ gives rise to 300-fold and 5-fold rate acceleration compared to the uncatalyzed reaction and Cu2+ ions, respectively. This work provides a simple and efficient strategy to construct the RNA-based catalysts that would expand the current nucleic acids-based catalysis and might hint the possible catalytic RNA in primordial chemistry.
Terpyridine-Cu(II) targeting human telomeric DNA to produce highly stereospecific G-quadruplex DNA metalloenzyme
Li, Yinghao,Cheng, Mingpan,Hao, Jingya,Wang, Changhao,Jia, Guoqing,Li, Can
, p. 5578 - 5585 (2015/09/28)
The cofactors commonly involved in natural enzymes have provided the inspiration for numerous advances in the creation of artificial metalloenzymes. Nevertheless, to design an appropriate cofactor for a given biomolecular scaffold or vice versa remains a challenge in developing efficient catalysts in biochemistry. Herein, we extend the idea of G-quadruplex-targeting anticancer drug design to construct a G-quadruplex DNA metalloenzyme. We found that a series of terpyridine-Cu(ii) complexes (CuLn) can serve as excellent cofactors to dock with human telemetric G-quadruplex DNA. The resulting G-quadruplex DNA metalloenzyme utilising CuL1 catalyzes an enantioselective Diels-Alder reaction with enantioselectivity of >99% enantiomeric excess and about 73-fold rate acceleration compared to CuL1 alone. The terpyridine-Cu(ii) complex cofactors demonstrate dual functions, both as an active site to perform catalysis and as a structural regulator to promote the folding of human telemetric G-quadruplex DNA towards excellent catalysts.
