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Related Concept Videos

Cofactors and Coenzymes01:27

Cofactors and Coenzymes

Enzymes require additional components for proper function. There are two such classes of molecules: cofactors and coenzymes. Cofactors are metallic ions and coenzymes are non-protein organic molecules. Both of these types of helper molecule can be tightly bound to the enzyme or bound only when the substrate binds.
Cofactors and Coenzymes01:27

Cofactors and Coenzymes

Enzymes require additional components for proper function. There are two such classes of molecules: cofactors and coenzymes. Cofactors are metallic ions and coenzymes are non-protein organic molecules. Both of these types of helper molecule can be tightly bound to the enzyme or bound only when the substrate binds.
Cofactors and Coenzymes01:24

Cofactors and Coenzymes

Enzymes are proteins made of amino acids. The functional group of each constituent amino acid catalyzes a wide variety of chemical reactions via ionic interactions or acid-base reactions. However, amino acids cannot catalyze oxidation-reduction and group transfer reactions and need to be aided by non-protein components called cofactors. Cofactors are also referred to as the chemical teeth of an enzyme.
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C–C Bond Formation: Aldol Condensation Overview01:10

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Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

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Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

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A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
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Published on: October 2, 2012

C-O bond formation by polyketide synthases.

Hyung-Jin Kwon1, Wyatt C Smith, A Janelle Scharon

  • 1Division of Pharmaceutical Sciences and, Department of Chemistry, University of Wisconsin, Madison, WI 53705, USA.

Science (New York, N.Y.)
|August 24, 2002
PubMed
Summary

Polyketide synthases (PKSs) typically form carbon-carbon bonds. However, two specific PKS beta-ketoacyl synthase (KS) domains, NonJ and NonK, were found to form carbon-oxygen bonds, enabling novel PKS engineering.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Synthetic Biology

Background:

  • Polyketide synthases (PKSs) are crucial enzymes that construct polyketide molecules via sequential condensation reactions.
  • The beta-ketoacyl synthase (KS) domain is the catalytic core responsible for the C-C bond-forming step in PKS assembly.
  • Understanding KS domain mechanisms is key to engineering PKS for novel compound synthesis.

Purpose of the Study:

  • To investigate the catalytic mechanism of two highly homologous KS domains, NonJ and NonK, from the nonactin biosynthesis pathway.
  • To determine if NonJ and NonK exhibit canonical C-C bond formation or an alternative catalytic activity.
  • To explore the potential of these KS domains for PKS engineering and expanding polyketide diversity.

Main Methods:

  • Genetic characterization of the nonactin biosynthesis gene cluster in Streptomyces griseus.
  • Biochemical assays to analyze the activity of NonJ and NonK KS domains.
  • Comparative analysis of NonJ and NonK with known KS domains.

Main Results:

  • NonJ and NonK KS domains were identified and characterized from Streptomyces griseus.
  • These KS domains catalyze the condensation of acyl coenzyme A (CoA) substrates by forming C-O bonds, deviating from the typical C-C bond formation.
  • The identified KS domains show high homology to known KSs, suggesting a divergence in catalytic function within the KS family.

Conclusions:

  • The discovery of NonJ and NonK reveals a novel catalytic activity within PKS KS domains, forming C-O rather than C-C bonds.
  • This unique chemistry offers new possibilities for PKS engineering.
  • Harnessing this C-O bond-forming capability can significantly broaden the scope and diversity of polyketide biosynthesis, leading to novel compounds.