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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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Introduction
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AvmM catalyses macrocyclization through dehydration/Michael-type addition in alchivemycin A biosynthesis.

Hong Jie Zhu1, Bo Zhang1, Wanqing Wei2

  • 1State Key Laboratory of Pharmaceutical Biotechnology, Chemistry and Biomedicine Innovation Centre, Institute of Artificial Intelligence Biomedicine, School of Life Sciences, Nanjing University, Nanjing, 210023, China.

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Researchers discovered a new enzyme, AvmM, that builds complex macrocyclic structures in natural products. This enzyme uses a unique dehydration and Michael-type addition strategy to form the alchivemycin A scaffold.

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Area of Science:

  • Biochemistry
  • Natural Product Biosynthesis
  • Enzymology

Background:

  • Macrocyclization is crucial for creating bioactive natural products.
  • Nature employs diverse enzymatic strategies for macrocycle formation.
  • Alchivemycin A is a bioactive natural product containing a macrocyclic core.

Purpose of the Study:

  • To identify and characterize the enzyme responsible for macrocyclization in alchivemycin A biosynthesis.
  • To elucidate the mechanism of macrocycle formation catalyzed by the enzyme AvmM.
  • To uncover novel macrocyclization strategies in natural product biosynthesis.

Main Methods:

  • Gene deletion studies in vivo to confirm enzyme function.
  • In vitro biochemical assays to analyze enzyme activity.
  • Isotope labeling experiments to trace reaction pathways.
  • Crystallography, DFT calculations, and MD simulations for mechanistic insights.

Main Results:

  • Identification and characterization of the enzyme AvmM.
  • AvmM catalyzes a tandem dehydration and Michael-type addition reaction.
  • The enzyme constructs the 16-membered macrocyclic scaffold of alchivemycin A.
  • Mechanistic studies revealed substrate-assisted catalysis involving a tenuazonic acid-like moiety.

Conclusions:

  • AvmM employs a novel enzymatic strategy for macrocyclization.
  • This study reveals a previously uncharacterized pathway in natural product biosynthesis.
  • The findings expand our understanding of enzymatic macrocycle formation.