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Related Concept Videos

Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Regulation of Metabolism01:19

Regulation of Metabolism

Cellular needs and conditions vary from cell to cell and change within individual cells over time. For example, the required enzymes and energetic demands of stomach cells are different from those of fat storage cells, skin cells, blood cells, and nerve cells. Furthermore, a digestive cell works much harder to process and break down nutrients during the time that closely follows a meal compared with many hours after a meal. As these cellular demands and conditions vary, so do the amounts and...
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Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Substrate control through per-O-methylation of cyclodextrin acids.

Thomas H Fenger1, Mikael Bols

  • 1Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Kbh Ø, Denmark.

Chemical Communications (Cambridge, England)
|September 28, 2010
PubMed
Summary

Per-O-methylated cyclodextrins with specific modifications showed significant glycosidase enzyme catalysis, accelerating reactions by up to 1000-fold. These findings highlight the importance of the cyclodextrin

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Published on: November 20, 2014

Area of Science:

  • Carbohydrate Chemistry
  • Enzyme Catalysis
  • Supramolecular Chemistry

Background:

  • Cyclodextrins are cyclic oligosaccharides with a hydrophobic cavity and hydrophilic exterior.
  • Per-O-methylation modifies cyclodextrin properties, influencing their interactions and catalytic potential.
  • Understanding structure-activity relationships in modified cyclodextrins is crucial for designing artificial enzymes.

Purpose of the Study:

  • To investigate the glycosidase activity of specifically modified per-O-methylated cyclodextrins.
  • To determine the influence of substituent position and type on catalytic efficiency.
  • To elucidate the mechanism of substrate binding and catalysis.

Main Methods:

  • Synthesis of per-O-methylated cyclodextrins with 2-O-acetate, 2-O-propanoate, or 6-carboxylate modifications.
  • Assay of glycosidase activity using p-nitrophenyl glycosides as substrates.
  • Kinetic analysis to determine rate accelerations and catalytic efficiency.

Main Results:

  • Per-O-methylated cyclodextrins with 2-O-acetate and 2-O-propanoate substituents exhibited significant enzyme-like catalysis.
  • Rate accelerations of 500-1000 were observed for these modified cyclodextrins.
  • The 6-carboxylate derivative showed only marginal catalytic activity.

Conclusions:

  • Per-O-methylated cyclodextrins can act as effective catalysts for glycosidase reactions.
  • Substituents at the 2-O position promote catalysis by directing substrate binding to the secondary face of the cyclodextrin.
  • These findings provide insights into the design of artificial enzymes based on cyclodextrin scaffolds.