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Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
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Cholinesterases are a group of serine hydrolase enzymes that play a crucial role in the breakdown of choline esters. The two primary types of cholinesterases are acetylcholinesterases (AChEs) and butyrylcholinesterase (BuChEs), which differ in their distribution, function, and substrate specificity. AChEs, also known as true cholinesterases, specifically hydrolyze acetylcholine, while BuChEs, often referred to as pseudocholinesterases, can hydrolyze various choline esters, including...
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Environmental role of aromatic carboxylesterases.

Venkatesh M Ghodke1, Narayan S Punekar1

  • 1Department of Biosciences and Bioengineering, Indian Institute of Technology Bombay, Mumbai, India.

Environmental Microbiology
|September 16, 2021
PubMed
Summary
This summary is machine-generated.

Carboxylesterases are crucial hydrolases that break down various esters. Aromatic carboxylesterases, which are rare, are vital for degrading difficult aromatic compounds and plastic waste.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Environmental Science

Background:

  • Carboxylesterases (EC 3.1.1.x) are diverse hydrolases that cleave ester bonds in numerous substrates, including drugs, pesticides, and plant components.
  • While some enzymes exhibit promiscuity, very few exclusively hydrolyze aromatic carboxylic acid esters due to steric and polar effects, making them inherently difficult to break down.
  • The environmental presence of aromatic carboxylesters has increased due to anthropogenic activities, posing challenges for natural degradation processes.

Purpose of the Study:

  • To highlight the unique challenges associated with the hydrolysis of aromatic carboxylesters.
  • To underscore the significance of carboxylesterases in addressing the environmental persistence of aromatic esters, including plastic waste.
  • To review the current literature on the evolution and catalytic efficiency of enzymes capable of hydrolyzing aromatic esters.

Main Methods:

  • Literature review and appraisal of existing research on carboxylesterases and ester hydrolysis.
  • Analysis of the chemical properties contributing to the difficulty in hydrolyzing aromatic esters (steric and polar effects).
  • Examination of the natural occurrence and evolution of enzymes targeting aromatic esters.

Main Results:

  • Aromatic carboxylesters are inherently resistant to hydrolysis compared to regular esters, requiring specialized enzymes.
  • Naturally occurring aromatic carboxylesterases are rare, but their prevalence is increasing due to human activities.
  • Enzymes capable of hydrolyzing aromatic esters are evolving but often exhibit low catalytic efficiency, necessitating further research.

Conclusions:

  • The hydrolysis of aromatic carboxylic esters presents a significant scientific and environmental challenge.
  • Carboxylesterases with specificity for aromatic esters are crucial for bioremediation and waste management, particularly for materials like polyethylene terephthalate.
  • Further research into the discovery and engineering of efficient aromatic carboxylesterases is essential to mitigate environmental pollution.