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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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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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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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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.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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.
Selection Rules: Photochemical Activation
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Efficient heterocyclisation by (di)terpene synthases.

S Mafu1, K C Potter1, M L Hillwig1

  • 1Roy J. Carver Department of Biochemistry, Biophysics & Molecular Biology, Iowa State University, Ames, IA 50011, USA. rjpeters@iastate.edu.

Chemical Communications (Cambridge, England)
|July 28, 2015
PubMed
Summary
This summary is machine-generated.

Terpene synthases can efficiently form cyclic ethers like manoyl oxide. Modifying single amino acids in terpene synthases creates bifunctional enzymes with novel activities for producing these compounds.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Organic Chemistry

Background:

  • Terpene synthases are enzymes that catalyze the formation of diverse terpene skeletons.
  • The mechanism by which terpene synthases achieve cyclic ether formation, specifically heterocyclisation, remains poorly understood.
  • Previous studies have identified some cyclic ether-forming terpene synthases, but the underlying principles are unclear.

Purpose of the Study:

  • To investigate the basis for heterocyclisation in terpene synthases.
  • To explore the potential of terpene synthases to produce manoyl oxide isomers.
  • To engineer novel bifunctional terpene synthases with enhanced enzymatic activity.

Main Methods:

  • Utilized various (di)terpene synthases, including ancestral ent-kaurene synthase.
  • Employed stereochemically appropriate substrates for enzymatic reactions.
  • Introduced single residue mutations in the active site to alter substrate production.
  • Analyzed the products of enzymatic reactions to identify manoyl oxide isomers.

Main Results:

  • Numerous (di)terpene synthases, including ent-kaurene synthase, efficiently produced manoyl oxide isomers from appropriate substrates.
  • Demonstrated that terpene synthases can readily accomplish heterocyclisation reactions.
  • Engineered bifunctional enzymes through single residue changes, leading to efficient production of manoyl oxide isomers.
  • Identified novel enzymatic activity in engineered terpene synthases.

Conclusions:

  • Terpene synthases possess an inherent capability for facile heterocyclisation, leading to the formation of cyclic ethers like manoyl oxide.
  • Single amino acid modifications can create bifunctional terpene synthases with novel activities, expanding their catalytic repertoire.
  • This study provides new insights into the mechanisms of terpene biosynthesis and offers a platform for enzyme engineering.