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Related Concept Videos

Oxidative Cleavage of Alkenes: Ozonolysis01:46

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 Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
Oxidation of Alcohols02:37

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: Anti Dihydroxylation with Peroxy Acids02:04

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.
Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...

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Immobilization of Multi-biocatalysts in Alginate Beads for Cofactor Regeneration and Improved Reusability
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The depolymerization of sodium alginate by oxidative degradation.

Shirui Mao1, Tingting Zhang, Wei Sun

  • 1School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, China. shiruimao156@hotmail.com

Pharmaceutical Development and Technology
|May 28, 2011
PubMed
Summary

Oxidative depolymerization effectively reduces alginate molecular weight (Mw), yielding low Mw oligosaccharides. Key factors influencing this process include temperature, hydrogen peroxide concentration, and pH, crucial for applications like drug delivery systems.

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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Drug Delivery

Background:

  • Alginate is widely utilized as a carrier for macromolecules and in gene delivery.
  • Its efficacy in these applications is dependent on molecular weight (Mw).
  • Controlled modification of alginate Mw is essential for optimizing its performance.

Purpose of the Study:

  • To investigate factors influencing the oxidative depolymerization of alginate.
  • To determine the optimal conditions for preparing low molecular weight alginate fragments.
  • To assess the potential of these fragments in drug delivery systems.

Main Methods:

  • Oxidative depolymerization using hydrogen peroxide.
  • Monitoring Mw changes over time and under varying reaction conditions (temperature, H2O2 concentration, initial alginate concentration, pH).
  • Characterization using Fourier Transform Infrared (FTIR) spectroscopy and UV spectroscopy.

Main Results:

  • Depolymerization primarily occurred within the first hour.
  • Mw reduction was dependent on temperature (significant decrease at 40°C), hydrogen peroxide concentration, and pH (optimal range 5-7).
  • FTIR confirmed glycosidic bond breakage, while UV spectroscopy indicated no structural changes.

Conclusions:

  • Oxidative depolymerization is an effective method for producing low Mw alginate oligosaccharides.
  • Reaction parameters like temperature, H2O2 concentration, and pH can be controlled to tailor Mw.
  • This technique offers a convenient approach for preparing alginate fragments potentially useful in drug delivery systems.