Amino–Acetone‐Bridged Cyclodextrins ― Artificial Alcohol Oxidases

Marinescu, Lavinia; Doyagüez, Elisa G.; Petrillo, Marta; Fernández-Mayoralas, Alfonso; Bols, Mikael

doi:10.1002/ejoc.200901099

Cited by 16 publications

(2 citation statements)

References 57 publications

(22 reference statements)

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“…Marinescu et al reported the synthesis of new αand β-cyclodextrin derivatives with good enzyme-like activity in the oxidation of alcohols with H 2 O 2 [66]. In this context, different cyclodextrin derivatives (Figure 2, left) have also been described to catalyse the oxidation of anilines to nitroarenes [67].…”

Section: Oxidation With Hydrogen Peroxidementioning

confidence: 99%

Synthesis of Nitroarenes by Oxidation of Aryl Amines

Capperucci

Tanini

2022

Chemistry

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Nitro compounds are an important class of organic molecules with broad application in organic synthesis, medicinal chemistry, and materials science. Among the variety of methodologies available for their synthesis, the direct oxidation of primary amines represents an attractive alternative route. Efforts towards the development of oxidative procedures for the synthesis of nitro derivatives have spanned over the past decades, leading to a wide variety of protocols for the selective oxidative conversion of amines to nitro derivatives. Methods for the synthesis of nitroarenes via oxidation of aryl amines, with particular emphasis on recent advances in the field, are summarised in this review.

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Section: Oxidation With Hydrogen Peroxidementioning

confidence: 99%

Synthesis of Nitroarenes by Oxidation of Aryl Amines

Capperucci

Tanini

2022

Chemistry

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“…Cyclodextrins are cyclic oligosaccharides of at least six α-1-4-linked α-Dglucopyranoside units, with a peculiar internal toroidal shape with a cavity able to recognize and host several molecules. In the past, CDs had already been used to build enzyme models [175], and Li-Wu et al used this strategy to study Se-and Te-based artificial enzymes, highlighting a higher efficiency of Te-based CDs in catalyzing the model reaction (NADPH), especially when the chalcogens are inserted in the 2-position rather than in the 6position. Moreover, the activity of dual-bridged enzymatic mimics was found to be higher than that of single-bridged ones.…”

Section: Other Classes Of Diselenides: Towards Macromolecular Gpx Mimicsmentioning

confidence: 99%

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Tiezza¹,

Ribaudo

Orian³

2019

COC

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Organodiselenides are an important class of compounds characterized by the presence of two adjacent covalently bonded selenium nuclei. Among them, diaryldiselenides and their parent compound diphenyl diselenide attract continuing interest in chemistry as well as in close disciplines like medicinal chemistry, pharmacology and biochemistry. A search in SCOPUS database has revealed that in the last three years 105 papers have been published on the archetypal diphenyl diselenide and its use in organic catalysis and drug tests. The reactivity of the Se-Se bond and the redox properties of selenium make diselenides efficient catalysts for numerous organic reactions, such as Bayer- Villiger oxidations of aldehydes/ketones, epoxidations of alkenes, oxidations of alcohols and nitrogen containing compounds. In addition, organodiselenides might find application as mimics of glutathione peroxidase (GPx), a family of enzymes, which, besides performing other functions, regulate the peroxide tone in the cells and control the oxidative stress level. In this review, the essential synthetic and reactivity aspects of organoselenides are collected and rationalized using the results of accurate computational studies, which have been carried out mainly in the last two decades. The results obtained in silico provide a clear explanation of the anti-oxidant activity of organodiselenides and more in general of their ability to reduce hydroperoxides. At the same time, they are useful to gain insight into some aspects of the enzymatic activity of the GPx, inspiring novel elements for rational catalyst and drug design.

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Artificial Enzyme Mimics

Geibel

Merschky

Rether

et al. 2012

Supramolecular Chemistry

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Enzymes are among the most effective catalysts known so far both in terms of their efficiency as well as selectivity. They can achieve rate accelerations of up to a factor of 10 11 and more, and sometimes react exclusively with only one single stereoisomer of a substrate if required. Enzymes make use of various different mechanisms of catalysis such as transition‐state binding, acid–base catalysis, nucleophilic catalysis, entropic control of reactions, and so on, with roughly half the known enzymes using metal ions while the other half solely relies on organic functional groups. Owing to these fascinating features of enzymes, chemists have tried to mimic enzymes early on developing artificial enzyme models. Over the years, a multitude of functional artificial enzyme models for very different types and classes of enzymes were developed, some closely mimicking the mode of action of their natural counterparts whereas others just adopt some general features found in enzymes. We briefly discuss some selected examples of artificial enzyme mimics in this review. Of course, the following examples are only a few picked out of a great variety. We do not attempt to provide a complete overview in respect to enzymes that are mimicked or models that were developed, but rather focus on the different approaches and concepts used to imitate an enzyme. The choice of examples is purely reflecting our personal preferences and is not implied to indicate that any work not mentioned is less interesting. We have arranged the examples of enzyme mimics and presented roughly according to their increasing chemical and structural complexity, starting with simple metal complexes (Section 1), then discussing cyclodextrin and related enzyme mimics (Section 2) before focusing on polymer‐ and dendrimer‐derived systems (Section 3). Miniproteins and oligopeptides with defined structures are then discussed (Section 4) before we end with a brief description of catalytic antibodies (Section 5).

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Amino–Acetone‐Bridged Cyclodextrins ― Artificial Alcohol Oxidases

Cited by 16 publications

References 57 publications

Synthesis of Nitroarenes by Oxidation of Aryl Amines

Synthesis of Nitroarenes by Oxidation of Aryl Amines

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Artificial Enzyme Mimics

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