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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Esters to Carboxylic Acids: Saponification01:25

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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.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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E1 Reaction: Stereochemistry and Regiochemistry02:43

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One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
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Promiscuous Esterases Counterintuitively Are Less Flexible than Specific Ones.

Christina Nutschel1, Cristina Coscolín2, Benoit David3

  • 1John von Neumann Institute for Computing (NIC), Jülich Supercomputing Centre (JSC), Institute of Biological Information Processing (IBI-7: Structural Biochemistry), and Institute of Bio- and Geosciences (IBG-4: Bioinformatics), Forschungszentrum Jülich GmbH, 52425 Jülich, Germany.

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Summary

Promiscuous esterases are unexpectedly less flexible and more stable than specific ones. Rigidity analysis can identify these enzymes for biotechnology and synthetic chemistry applications.

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Area of Science:

  • Enzymology and Structural Biology
  • Biocatalysis and Biotechnology

Background:

  • Enzyme promiscuity is crucial for fundamental understanding and applications.
  • Generally, promiscuous enzymes are considered more flexible, but the opposite is less studied.

Purpose of the Study:

  • To investigate the molecular basis of substrate promiscuity in esterases.
  • To explore the relationship between enzyme flexibility, stability, activity, and promiscuity.

Main Methods:

  • Comprehensive experimental screening of 147 esterases against 96 esters.
  • Computationally efficient rigidity analyses to assess enzyme structural dynamics.

Main Results:

  • Promiscuous esterases were found to be significantly less flexible than specific esterases.
  • Promiscuous esterases exhibited higher thermostability and increased specific activity.
  • A model suggests specific esterases use flexibility for conformational proofreading.

Conclusions:

  • Enzyme rigidity analysis can identify promiscuous esterases.
  • These findings offer starting points for enzyme engineering in biotechnology and synthetic chemistry.