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Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

Oxidation of Alcohols

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Pyruvate Oxidation

Pyruvate Oxidation

After glycolysis, the charged pyruvate molecules enter the mitochondria via active transport and undergo three enzymatic reactions. These reactions ensure that pyruvate can enter the next metabolic pathway so that energy stored in the pyruvate molecules can be harnessed by the cells.
First, the enzyme pyruvate dehydrogenase removes the carboxyl group from pyruvate and releases it as carbon dioxide. The stripped molecule is then oxidized and releases electrons, which are then picked up by NAD+...

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Related Experiment Video

Updated: May 13, 2026

Benchtop Immobilized Metal Affinity Chromatography, Reconstitution and Assay of a Polyhistidine Tagged Metalloenzyme for the Undergraduate Laboratory

Benchtop Immobilized Metal Affinity Chromatography, Reconstitution and Assay of a Polyhistidine Tagged Metalloenzyme for the Undergraduate Laboratory

Published on: August 23, 2018

Alkylglycerol monooxygenase.

Katrin Watschinger¹, Ernst R Werner

¹Division of Biological Chemistry, Biocenter, Innsbruck Medical University, Innsbruck, Austria.

|February 27, 2013

Summary

Alkylglycerol monooxygenase, a crucial enzyme for cleaving ether bonds, was finally sequenced in 2010. Research now aims to uncover its physiological functions in mammals and model organisms.

Area of Science:

Biochemistry
Enzymology
Membrane protein research

Background:

Alkylglycerol monooxygenase (E.C. 1.14.16.5) is the sole enzyme identified for cleaving ether bonds in alkylglycerols and related phospholipids.
Despite its discovery in 1964, the enzyme's labile nature hindered purification and characterization until recently.

Purpose of the Study:

To identify and characterize the sequence of the alkylglycerol monooxygenase enzyme.
To investigate the enzyme's catalytic mechanism and active site characteristics.
To explore the physiological relevance of alkylglycerol monooxygenase across different species.

Main Methods:

Bioinformatic analysis to select candidate genes for the enzyme.
Recombinant expression of candidate genes.

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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

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Published on: November 8, 2019

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Benchtop Immobilized Metal Affinity Chromatography, Reconstitution and Assay of a Polyhistidine Tagged Metalloenzyme for the Undergraduate Laboratory

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Published on: November 8, 2019

Development of a sensitive fluorescence-based assay for enzymatic activity monitoring.

Site-directed mutagenesis to probe the active site and cofactor interactions.

Main Results:

The sequence of the labile integral membrane enzyme was assigned in 2010.
The enzyme contains a fatty acid hydroxylase protein motif signature, suggesting a di-iron catalytic center.
Mutagenesis identified key active site regions and a crucial glutamate residue for tetrahydrobiopterin binding.

Conclusions:

The characterization of alkylglycerol monooxygenase provides a foundation for understanding its biochemical properties.
The enzyme's conserved nature across mammals, zebrafish, and C. elegans highlights its biological importance.
Future research will focus on elucidating the specific physiological roles of this enzyme.