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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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The carbonic acid-bicarbonate buffer system is critical for maintaining the body's pH balance. It operates on the equilibrium:
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Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Metabolic reactions in the body produce nonvolatile acids, such as sulfuric acid, which generate an acid load of approximately 1 mEq of H+ per kilogram of body weight daily. Excreting H+ in the urine is essential to balance this acid load.
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Bacterial β-carbonic anhydrases.

Marta Ferraroni1

  • 1Dipartimento di Chimica "Ugo Schiff", Università di Firenze, Sesto Fiorentino, Firenze, Italia.

The Enzymes
|September 2, 2024
PubMed
Summary

Beta-carbonic anhydrases (β-CAs) are bacterial zinc enzymes. Class II β-CAs have an inactive form regulated by pH and bicarbonate binding, involving an Asp-Arg dyad.

Area of Science:

  • Biochemistry
  • Enzymology

Background:

  • Beta-carbonic anhydrases (β-CAs) are zinc metalloenzymes crucial for bacterial growth and survival.
  • Structurally distinct from other carbonic anhydrase classes, β-CAs feature a unique active site at the dimer interface, with the zinc ion coordinated by two cysteines and one histidine.

Purpose of the Study:

  • To investigate the structural and mechanistic differences between β-CA classes.
  • To elucidate the pH-dependent regulation and bicarbonate binding in class II β-CAs.

Main Methods:

  • Structural analysis of β-CA active sites.
  • Biochemical assays to determine enzyme activity and ligand binding.
  • Computational modeling to understand pH-induced conformational changes.

Main Results:

Keywords:
AllostericBacteriaBicarbonateMechanismX-ray structureZinc ionβ-Carbonic anhydrase

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  • β-CAs are classified into two subgroups based on the fourth zinc ligand: Class I (hydroxide, active) and Class II (Asp residue, inactive below pH 8).
  • Class II β-CAs exhibit pH-induced regulation via an Asp-Arg dyad that controls active site solvent access.
  • A bicarbonate-specific allosteric site and a promiscuous escort site at the dimer interface were identified, influencing enzyme activity.

Conclusions:

  • The Asp-Arg dyad and bicarbonate binding sites are key to the regulatory mechanism of class II β-CAs.
  • Understanding these mechanisms provides insights into bacterial adaptation and potential therapeutic targets.