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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Sharpless Epoxidation02:57

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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Related Experiment Video

Updated: Jul 3, 2026

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
09:42

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes

Published on: January 16, 2016

[Engineering of squalene cyclizing enzymes].

Ikuro Abe1

  • 1School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan. abei@u-shizuoka-ken.ac.jp

Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan
|August 2, 2008
PubMed
Summary

Enzymes that cyclize squalene can create novel cyclic compounds from unnatural substrates. This study showcases bacterial and plant enzymes producing unique, complex polyprenoids and triterpenes.

Area of Science:

  • Biochemistry
  • Enzymology
  • Synthetic Biology

Background:

  • Squalene cyclizing enzymes exhibit broad substrate tolerance and catalytic potential.
  • These enzymes can accept non-physiological substrate analogues for sequential ring-forming reactions.
  • This plasticity enables the generation of unnatural cyclic triterpenes and polyprenoids.

Purpose of the Study:

  • To demonstrate the generation of novel cyclic polyprenoids using enzymatic conversion of chemically synthesized substrate analogues.
  • To highlight the catalytic plasticity of bacterial and plant squalene cyclizing enzymes.
  • To present specific examples of enzyme-catalyzed synthesis of unnatural cyclic compounds.

Main Methods:

  • Utilizing bacterial squalene: hopene cyclase from Alicyclobacillus acidocaldarius to form "supra-natural" hexacyclic polyprenoids and heteroaromatic ring-containing cyclic polyprenoids.

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Last Updated: Jul 3, 2026

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

  • Employing plant oxidosqualene: beta-amyrin cyclase from Pisum sativum for the enzymatic cyclization of modified substrate analogues (22,23-dihydro-2,3-oxidosqualene and 24,30-bisnor-2,3-oxidosqualene).
  • Enzymatic conversion of chemically synthesized substrate analogues.
  • Main Results:

    • Successful enzymatic formation of a "supra-natural" hexacyclic polyprenoid by bacterial squalene: hopene cyclase.
    • Synthesis of cyclic polyprenoids containing heteroaromatic rings using the bacterial enzyme.
    • Enzymatic cyclization of modified oxidosqualene substrates by the plant enzyme, yielding novel cyclic triterpenes.

    Conclusions:

    • The catalytic plasticity of squalene cyclizing enzymes allows for the creation of diverse and novel unnatural cyclic molecules.
    • Bacterial and plant enzymes can be effectively utilized to produce complex cyclic polyprenoids and triterpenes from synthetic analogues.
    • This approach offers a powerful strategy for generating novel chemical entities with potential applications in various fields.