Cyclodextrin‐Based Artificial Enzymes: Synthesis and Function

Pedersen, Christian; Bols, Mikael

doi:10.1002/9781118736449.ch11

Cited by 7 publications

(2 citation statements)

References 101 publications

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“…These naturally occurring cyclic oligosaccharides are composed of glucose units in 4 C 1 chair conformations, with a hydrogen bond network formed between the secondary hydroxyl groups, creating a conical shape with an internal hydrophobic cavity, conferring the ability to form host–guest or inclusion complexes with a great variety of molecules and rendering them one of the most important supramolecular host families. Because of these inclusion properties, CDs are displayed as being potentially useful as drug and gene delivery systems, artificial enzymes or catalysts, just to cite a few.…”

Section: Introductionmentioning

confidence: 99%

Radical-Mediated C–H Functionalization: A Strategy for Access to Modified Cyclodextrins

et al. 2016

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This version is available at https://strathprints.strath.ac.uk/58624/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.uk derivative shows a severe distortion toward a narrower elliptical shape for the primary face.

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Section: Introductionmentioning

confidence: 99%

Radical-Mediated C–H Functionalization: A Strategy for Access to Modified Cyclodextrins

et al. 2016

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“…CD derivatives have been increasingly applied in catalysis and biomimetic reactions [3–4] thanks to host–guest interactions and to the non-toxic, chiral skeleton of CDs. More specifically, CDs applied in reactions involving metal catalysis [5], organocatalysis [6] and artificial enzymes [7] have been recently studied, thus highlighting their high potential as effective catalysts.…”

Section: Introductionmentioning

confidence: 99%

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

Tichá

Hybelbauerová

Jindřich

2019

Beilstein J. Org. Chem.

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The preparation of new organocatalysts for asymmetric syntheses has become a key stage of enantioselective catalysis. In particular, the development of new cyclodextrin (CD)-based organocatalysts allowed to perform enantioselective reactions in water and to recycle catalysts. However, only a limited number of organocatalytic moieties and functional groups have been attached to CD scaffolds so far. Cinchona alkaloids are commonly used to catalyze a wide range of enantioselective reactions. Thus, in this study, we report the preparation of new α- and β-CD derivatives monosubstituted with cinchona alkaloids (cinchonine, cinchonidine, quinine and quinidine) on the primary rim through a CuAAC click reaction. Subsequently, permethylated analogs of these cinchona alkaloid–CD derivatives also were synthesized and the catalytic activity of all derivatives was evaluated in several enantioselective reactions, specifically in the asymmetric allylic amination (AAA), which showed a promising enantiomeric excess of up to 75% ee. Furthermore, a new disubstituted α-CD catalyst was prepared as a pure AD regioisomer and also tested in the AAA. Our results indicate that (i) the cinchona alkaloid moiety can be successfully attached to CD scaffolds through a CuAAC reaction, (ii) the permethylated cinchona alkaloid–CD catalysts showed better results than the non-methylated CDs analogues in the AAA reaction, (iii) promising enantiomeric excesses are achieved, and (iv) the disubstituted CD derivatives performed similarly to monosubstituted CDs. Therefore, these new CD derivatives with cinchona alkaloids effectively catalyze asymmetric allylic aminations and have the potential to be successfully applied in other enantioselective reactions.

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Easy Access to Modified Cyclodextrins by an Intramolecular Radical Approach

et al. 2015

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A simple method to modify the primary face of cyclodextrins (CDs) is described. The 6 I -O-yl radical of a-, b-, and g-CDs regioselectively abstracts the H5 II , located in the adjacent d-glucose unit, by an intramolecular 1,8-hydrogenatom-transfer reaction through a geometrically restricted ninemembered transition state to give a stable 1,3,5-trioxocane ring. The reaction has been extended to the 1,4-diols of a-and b-CD to give the corresponding bis(trioxocane)s. The C 2 -symmetric bis(trioxocane) corresponding to the a-CD is a stable crystalline solid whose structure was confirmed by X-ray diffraction analysis. The calculated geometric parameters confirm that the primary face is severely distorted toward a narrower elliptical shape for this rim.

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Cyclodextrin‐Based Artificial Enzymes: Synthesis and Function

Cited by 7 publications

References 101 publications

Radical-Mediated C–H Functionalization: A Strategy for Access to Modified Cyclodextrins

Radical-Mediated C–H Functionalization: A Strategy for Access to Modified Cyclodextrins

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

Easy Access to Modified Cyclodextrins by an Intramolecular Radical Approach

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