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Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

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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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Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
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Glutathione, a tripeptide made up of glutamate, cysteine, and glycine, is a critical player in the detoxification of drugs and xenobiotics via a process known as glutathione conjugation or mercapturic acid formation. This phase II biotransformation reaction involves the covalent binding of glutathione to a drug or its metabolite, enhancing the compound's water solubility and enabling its excretion.
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Phase II Reactions: Miscellaneous Conjugation Reactions01:19

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Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
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Vitamin B12 catalysed reactions.

Maciej Giedyk1, Katarzyna Goliszewska, Dorota Gryko

  • 1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. dorota.gryko@icho.edu.pl.

Chemical Society Reviews
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Vitamin B12 (cobalamin) is a natural organometallic catalyst crucial for biological processes. This review explores its use in environmentally friendly organic synthesis, highlighting its potential for sustainable cobalt catalysis.

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Area of Science:

  • Biochemistry
  • Organometallic Chemistry
  • Green Chemistry

Background:

  • Vitamin B12 (cobalamin) is a unique, naturally occurring organometallic molecule.
  • It functions as a cofactor for essential enzymes in DNA synthesis, nervous system function, and red blood cell formation.
  • The cobalt-carbon bond cleavage and formation are key to its enzymatic activity.

Purpose of the Study:

  • To review cobalamin-catalyzed organic reactions.
  • To highlight the potential of cobalamin as an environmentally friendly catalyst in organic synthesis.
  • To provide foundational knowledge for utilizing cobalamin's catalytic capabilities.

Main Methods:

  • Literature review of cobalamin-catalyzed reactions.
  • Analysis of cobalamin's role in enzymatic processes.
  • Discussion of cobalamin's application in sustainable cobalt catalysis.

Main Results:

  • Cobalamin (1) is a nontoxic, naturally occurring cobalt complex.
  • It has been successfully employed as a catalyst in various Co-mediated organic reactions.
  • Cobalamin catalysis offers a promising route for green chemistry applications.

Conclusions:

  • Cobalamin is a versatile and sustainable catalyst for organic synthesis.
  • Its natural origin and benign properties make it ideal for green chemistry.
  • Harnessing cobalamin's catalytic potential can lead to more environmentally friendly chemical processes.