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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.

Preparation of Epoxides

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...

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Hydroboration-Oxidation of Alkenes

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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.

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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.

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Updated: Sep 17, 2025

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Biotin-Initiated Poly(oxazoline)s.

Joseph A Garcia¹, Ashley Vergara Mendez¹, Ellen M Sletten¹

¹Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.

|July 2, 2025

Summary

This summary is machine-generated.

Researchers developed a simple method to create biotinylated poly(oxazoline)s (P(Ox)), offering a promising alternative to poly(ethylene glycol) (PEG) for biochemical assays. These new polymers exhibit high efficacy in biotin-streptavidin binding applications.

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Published on: February 6, 2019

Area of Science:

Polymer Chemistry
Bioconjugation Chemistry
Materials Science

Background:

Biotinylated polymers are crucial for biochemical assays due to the strong biotin-(strept)avidin interaction.
Poly(ethylene glycol) (PEG) is widely used but faces increasing immunogenicity concerns.
There is a need for alternative hydrophilic polymers with tunable properties and reduced immunogenicity.

Purpose of the Study:

To develop a facile method for synthesizing end-functionalized biotinylated poly(oxazoline)s (P(Ox)).
To present biotin-poly(2-methyl-2-oxazoline) as a viable alternative to PEG.
To demonstrate the versatility and efficacy of these novel biotinylated polymers in biochemical assays.

Main Methods:

Utilized an electrophilic biotin initiator for the end-group installation of biotin onto poly(oxazoline)s.
Synthesized biotin-poly(2-methyl-2-oxazoline) and explored variations in molecular weight, amphiphilicity, and functionality.
Evaluated the performance of the synthesized polymers in common biotin-streptavidin-based biochemical assays.

Main Results:

Successfully synthesized biotinylated poly(oxazoline)s with controlled molecular weights and architectures.
Demonstrated that biotin-poly(2-methyl-2-oxazoline) is a suitable alternative to PEG, addressing immunogenicity concerns.
Showcased the high efficacy of the biotinylated P(Ox) polymers in various biochemical assay formats.

Conclusions:

A straightforward method for preparing biotinylated poly(oxazoline)s has been established.
Biotinylated P(Ox) offers a versatile and effective alternative to PEG for biotin-(strept)avidin applications.
These novel polymers hold significant potential for advancing chemical and biochemical assays.