Permanganate–periodate Oxidation: Vi. The Oxidation of Various Aliphatic Compounds

Abstract

A study was made of the reaction of the permangallateperiodate reagent with a wide variety of aliphatic alcohols, polyols, aldehydes, acids, oxy-acids, ketones, ethers, and esters. Saturated monols, ketones, and ethers, as well as acetic, pelargonic, pyruvic, lactic, and oxalic acids reacted only very slowly. Glycols, olefinic alcohols, and unsaturated acids were cleaved to give predictable end products. Activated alcohols and ethyl acetoacetate reacted a t relatively high rates. Formic, glyoxylic, lactic, and malonic acids as well as 1,3-propanediol and 2,5-hexane dione reacted extensively and diethyl tartrate consumed as much oxidant as did tartaric acid. The oxidation of tetrahydrofurfuryl alcohol gave succinic acid instead of the expected tetrahydro-2-furoic acid. Saturated mono-and di-carboxylic acids, 3-hydroxy propionic acid, yvalero lactone, and saturated esters were stable towards the reagent.

A Phage Display Screening Derived Peptide with Affinity for the Adeninyl Moiety

“…Oxidation —In a typical study adapted from that of von Rudloff [ 15 ], beads (25.0 g, two batches) were put in a round bottle flask and acetone (20 mL) was added. While stirring, a solution of KMnO 4 (304 mg, 1.90 mmol) and NaIO 4 (10 g, 46.8 mmol) mixed in water (100 mL) was added dropwise, reaction left overnight.…”

Structural Characterization of Cork Lignin by Thioacidolysis and Permanganate Oxidation

“…C 5 to C 22 α,ω-diacids and one C 18 α,ω-diacid-9,10-epoxy were identified (Table 4). The permanganate/periodate system is a specific reagent for the oxidative cleavage of alkenic double bonds (Fatiadi 1987) and can cause over-oxidation of unsaturated fatty acids (Rudloff 1965) and of mid-chain hydroxy fatty acids (Gonzalez et al 1968). The permanganate/periodate system is a specific reagent for the oxidative cleavage of alkenic double bonds (Fatiadi 1987) and can cause over-oxidation of unsaturated fatty acids (Rudloff 1965) and of mid-chain hydroxy fatty acids (Gonzalez et al 1968).…”

Rapid quantification of total microcystins in cyanobacterial samples by periodate-permanganate oxidation and reversed-phase liquid chromatography

“…This method is believed to be an accurate method for screening for total MCs because it can measure MMPB derived from the unusual C 20 amino acid, ␤-amino acid (2S, 3S, 8S, 9S)-3-amino-9-methoxy-2, 6, 8-trimethyl-10-phenyldeca-4, 6-dienoic acid (Adda), which is a common constituent moiety of MCs [7]. Oxidizing toxins using the Lemieux oxidation method [33][34][35][36][37] have been widely used as a highly sensitive method for the detection of total MCs in a wide range of sample matrices, including cyanobacteria [38,39], animal tissues [40][41][42][43][44] and serum samples [45][46][47]. However, no studies have been conducted to evaluate the influence of reaction conditions on the formation of MMPB during the oxidation of MCs using permanganate-periodate.…”