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Related Concept Videos

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Engineering Polyketide Stereocenters with Ketoreductase Domain Exchanges.

Leah S Keiser1,2,3, Panarai Primrose Gatenil2,3,4, Yolanda Zhu1,2,3

  • 1Joint BioEnergy Institute, Emeryville, California 94608, United States.

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|November 4, 2025
PubMed
Summary

This study engineered polyketide synthases (PKSs) to control stereochemistry, successfully producing all four stereoisomers in vivo. Strategies for ketoreductase (KR) and ketosynthase (KS) domain modification advanced PKS engineering for novel pharmaceuticals.

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Area of Science:

  • Biochemistry
  • Synthetic Biology
  • Natural Product Biosynthesis

Background:

  • Polyketide synthases (PKSs) are crucial for producing diverse natural products, including pharmaceuticals.
  • Engineering PKSs for specific stereochemistry is challenging but vital for creating novel compounds.
  • Ketoreductase (KR) domains set stereocenters, making them key targets for PKS modification.

Purpose of the Study:

  • To systematically evaluate ketoreductase (KR) domain exchanges for engineering polyketide stereochemistry.
  • To investigate strategies for overcoming ketosynthase (KS) domain gatekeeping of altered intermediates.
  • To achieve in vivo production of all four stereoisomers in PKS systems.

Main Methods:

  • Optimized KR domain exchange methods.
  • Performed 44 KR domain exchanges across three PKS systems.
  • Investigated KS domain mutations and functional unit exchanges to alter stereocontrol.

Main Results:

  • Successfully obtained high production of all four stereoisomers in vivo.
  • Identified α-substituent configuration as critical for KS gatekeeping.
  • Demonstrated that KS domain modification strategies can overcome stereochemical constraints with varying trade-offs.

Conclusions:

  • Developed a comprehensive approach for engineering all four stereochemical configurations in PKSs.
  • Advanced the understanding of PKS stereochemistry control and rational engineering.
  • Enabled the creation of tailored polyketides with potential pharmaceutical applications.