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Related Concept Videos

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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Biosynthesis in Bacteria01:24

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Biosynthesis in bacteria is a fundamental anabolic process that generates essential macromolecules, including proteins, nucleic acids, lipids, and polysaccharides. These macromolecules are critical for cellular growth, replication, and function. The process is tightly regulated and energetically linked to catabolic pathways to ensure optimal resource utilization.Biosynthetic pathways begin with precursor metabolites such as pyruvate, acetyl-CoA, and glucose-6-phosphate derived from glycolysis,...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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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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Carbon dioxide fixation in prokaryotes enables the assimilation of inorganic carbon into organic molecules, supporting biosynthetic pathways, sustaining ecosystems, and contributing to the global carbon cycle. It also has industrial applications in carbon capture and bioproduct synthesis. Autotrophic organisms rely on this process to utilize CO₂ as a carbon source in diverse environments.The Calvin CycleThe Calvin cycle is the most widespread carbon fixation mechanism, primarily used by...
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Lipid Catabolism

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Triglycerides serve as crucial long-term energy storage molecules in microorganisms, providing a dense source of metabolic energy. Their breakdown is mediated by lipases, which hydrolyze triglycerides into glycerol and free fatty acids. Each of these components follows distinct metabolic pathways, ultimately contributing to ATP synthesis and cellular energy homeostasis.Glycerol MetabolismGlycerol, released from triglyceride hydrolysis, is phosphorylated by glycerol kinase to form...
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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Bacterial terpene cyclases.

Jeroen S Dickschat1

  • 1University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany. dickschat@uni-bonn.de.

Natural Product Reports
|November 14, 2015
PubMed
Summary

This review summarizes bacterial terpene cyclases characterized up to 2015. It details enzyme structures, products, and mechanisms, including widespread geosmin and 2-methylisoborneol synthases.

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Microbiology

Background:

  • Terpene cyclases are crucial enzymes in bacterial secondary metabolism.
  • Characterization of bacterial terpene cyclases has advanced significantly, revealing diverse structures and functions.
  • Understanding these enzymes is key to exploring novel bioactive compounds.

Purpose of the Study:

  • To provide a comprehensive summary of characterized bacterial terpene cyclases up to 2015.
  • To discuss the structures of enzyme products and crystallized enzymes.
  • To elucidate the mechanisms of terpene cyclases.

Main Methods:

  • Literature review of scientific publications up to 2015.
  • Analysis of structural data for bacterial terpene cyclases and their products.

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  • Discussion of mechanistic studies on enzyme function.

    • Main Results:

    • A total of 63 bacterial terpene cyclases have been characterized.
    • Structures of various mono-, sesqui-, and diterpene cyclases are presented.
    • Mechanistic insights into enzyme catalysis and product formation are discussed, with special attention to geosmin and 2-methylisoborneol synthases.

    Conclusions:

    • Bacterial terpene cyclases exhibit diverse structural and mechanistic features.
    • The characterized enzymes provide a foundation for understanding terpene biosynthesis in bacteria.
    • Further research on these enzymes may lead to the discovery of new natural products.