DNA-based hybrid catalysis

Rioz‐Martínez, Ana; Roelfes, Gérard

doi:10.1016/j.cbpa.2014.12.033

Cited by 67 publications

(45 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In general, comparing with the high specificity and selectivity of duplex DNA‐based hybrid catalysts and conventional biocatalysts (such as enzymes), current G‐quadruplex‐based catalytic systems exhibit a high catalytic activity but are lack of a high specificity and selectivity. However, multiple G‐quadruplex structures (Scheme ) have more complexed topology and more structural variety than duplex DNA, which could potentially provide versatile binding sites for metal ligands enabling some unique asymmetric catalysis .…”

Section: Resultsmentioning

confidence: 99%

G‐quadruplex DNA‐based asymmetric catalysis of michael addition: Effects of sonication, ligands, and co‐solvents

Zhao

Shen

2016

Biotechnology Progress

View full text Add to dashboard Cite

There is an escalating interest of using double stranded DNA molecules as a chiral scaffold to construct metal-biomacromolecule hybrid catalysts for asymmetric synthesis. Several recent studies also evaluated the use of G-quadruplex DNA-based catalysts for asymmetric Diels-Alder and Friedel-Crafts reactions. However, there is still a lack of understanding of how different oligonucleotides, salts (such as NaCl and KCl), metal ligands and co-solvents affect the catalytic performance of quadruplex DNA-based hybrid catalysts. In this study, we aim to systematically evaluate these key factors in asymmetric Michael addition reactions, and to examine the conformational and molecular changes of DNA by circular dichroism (CD) spectroscopy and gel electrophoresis. We achieved up to 95% yield and 50% enantiomeric excess (ee) when the reaction of 2-acylimidazole 1a and dimethylmalonate was catalyzed by 5'-G3 (TTAG3 )3 -3' (G4DNA1) in 20 mM MOPS (pH 6.5) containing 50 mM KCl and 40 µM [Cu(dmbipy)(NO3 )2 ], and G4DNA1 was pre-sonicated in ice bath for 10 min prior to the reaction. G-quadruplex-based hybrid catalysts provide a new tool for asymmetric catalysis, but future mechanistic studies should be sought to further improve the catalytic efficiency. The current work presents a systematic study of asymmetric Michael addition catalyzed by G-quadruplex catalysts constructed via non-covalent complexing, and an intriguing finding of the effect of pre-sonication on catalytic efficiency. © 2016 American Institute of Chemical Engineers Biotechnol. Prog., 32:891-898, 2016.

show abstract

Section: Resultsmentioning

confidence: 99%

G‐quadruplex DNA‐based asymmetric catalysis of michael addition: Effects of sonication, ligands, and co‐solvents

Zhao

Shen

2016

Biotechnology Progress

View full text Add to dashboard Cite

show abstract

“…Two distinct strategies are developed for constructing DNA catalysts --i) in vitro selection from synthetic DNA libraries 1,2 and ii) anchoring transition metal complexes as cofactors to naturally occurring double stranded (ds) DNAs. 3,4 The former focuses on the transformation of nucleic acids and peptides, meanwhile asymmetric catalysis of small molecules is frequently applied in exploring the catalytic function of the latter. DNA is usually a double helix in vivo, but single stranded guanine-rich DNAs can fold into alternative structural forms known as G-quadruplex.…”

Section: Enantioselective Sulfoxidation Reaction Catalyzed By G-quadrmentioning

confidence: 99%

Enantioselective sulfoxidation reaction catalyzed by a G-quadruplex DNA metalloenzyme

Cheng

Zhou

et al. 2016

Chem. Commun.

View full text Add to dashboard Cite

show abstract

“…DNA is active in catalysis, and can be divided into types I and II, according to the source of DNA sequences . The sequences of type I and II DNA catalysts come from in vitro selected and naturally occurring DNA, respectively.…”

Section: Introductionmentioning

confidence: 99%

“…The sequences of type I and II DNA catalysts come from in vitro selected and naturally occurring DNA, respectively. The former mainly catalyze the transformations of nucleic acids and peptides, and the latter are usually used for asymmetric catalysis of small molecules . Acceleration of the reaction rate is the most important and fundamental function of DNA for type I DNA catalysts .…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Spectroscopic Insight into the Supramolecular Interactions in DNA‐Based Enantioselective Sulfoxidation

Cheng

Hao

et al. 2018

ChemBioChem

View full text Add to dashboard Cite

Interactions of copper(II)-bipyridine cofactors and thioanisole substrate with human telomeric G-quadruplex DNA were studied by UV/Vis absorption, circular dichroism, and fluorescence quenching titration. Three copper(II)-bipyridine complexes are equivalently anchored to the G-quadruplex scaffold at all five fluorescently labeled sites. Thioanisole interacts with the DNA architecture at both the second loop and 3' terminus in the absence or presence of copper(II)-bipyridine complexes. These nonspecificities in the weak interactions of Cu complexes and thioanisole with G-quadruplex might explain why DNA only affords a modest enantioselectivity in the oxidation of thioanisole. These findings provide insights toward the construction of highly enantioselective DNA-based catalysts.

show abstract

DNA-based hybrid catalysis

Cited by 67 publications

References 35 publications

G‐quadruplex DNA‐based asymmetric catalysis of michael addition: Effects of sonication, ligands, and co‐solvents

G‐quadruplex DNA‐based asymmetric catalysis of michael addition: Effects of sonication, ligands, and co‐solvents

Enantioselective sulfoxidation reaction catalyzed by a G-quadruplex DNA metalloenzyme

Fluorescence Spectroscopic Insight into the Supramolecular Interactions in DNA‐Based Enantioselective Sulfoxidation

Contact Info

Product

Resources

About