Kinetics of the Oxidative Degradation of rac-Serine by Aqueous Alkaline Permanganate

Halligudi, Nirmala; Desai, S. M.; Mavalangi, Surekha K.; Nandibewoor, Sharanappa T.

doi:10.1007/s007060050313

Cited by 8 publications

(5 citation statements)

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“…Serine is known to be sensitive to radical based oxidation . Reagents, such as hydrogen peroxide or peroxyacids, , and permanganate oxidation are commonly used conditions in the processing of the commercial heparins and are also used to prepare LMWHs . The linkage region-O-Ser OX has recently been reported in studies on glycol-split periodate oxidized LMWH products .…”

Section: Resultsmentioning

confidence: 99%

Bottom-Up Low Molecular Weight Heparin Analysis Using Liquid Chromatography-Fourier Transform Mass Spectrometry for Extensive Characterization

Steppich

Wang³

et al. 2014

Anal. Chem.

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Low molecular weight heparins (LMWHs) are heterogeneous, polydisperse, and highly negatively charged mixtures of glycosaminoglycan chains prescribed as anticoagulants. The detailed characterization of LMWH is important for the drug quality assurance and for new drug research and development. In this study, online hydrophilic interaction chromatography (HILIC) Fourier transform mass spectrometry (FTMS) was applied to analyze the oligosaccharide fragments of LMWHs generated by heparin lyase II digestion. More than 40 oligosaccharide fragments of LMWH were quantified and used to compare LMWHs prepared by three different manufacturers. The quantified fragment structures included unsaturated disaccharides/oligosaccharides arising from the prominent repeating units of these LMWHs, 3-O-sulfo containing tetrasaccharides arising from their antithrombin III binding sites, 1,6-anhydro ring-containing oligosaccharides formed during their manufacture, saturated uronic acid oligosaccharides coming from some chain nonreducing ends, and oxidized linkage region oligosaccharides coming from some chain reducing ends. This bottom-up approach provides rich detailed structural analysis and quantitative information with high accuracy and reproducibility. When combined with the top-down approach, HILIC LC-FTMS based analysis should be suitable for the advanced quality control and quality assurance in LMWH production.

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Section: Resultsmentioning

confidence: 99%

Bottom-Up Low Molecular Weight Heparin Analysis Using Liquid Chromatography-Fourier Transform Mass Spectrometry for Extensive Characterization

Steppich

Wang³

et al. 2014

Anal. Chem.

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“…Equation (14) requires that the relationship between 1/k obs and 1/[CAD] at constant [OH -] to be linear with a non-zero intercept on the 1/k obs axis as was experimentally satisfied (Fig. 5), from the intercept of such plot, thevalue of the rate constant of the slow step (k 3 ) was evaluated as 0.21 s -1 .…”

Section: Mechanism Of Oxidation In Alkaline Mediummentioning

confidence: 99%

“…The small intercept obtained in Figure 5 leads to simplify Eq. (14) to the following equation: 3 (Fig. 7).…”

Section: Mechanism Of Oxidation In Alkaline Mediummentioning

confidence: 99%

“…Oxidation reactions are significant field in organic synthesis. Permanganate ion is an efficient oxidant in acidic, neutral and alkaline media [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] which still remains as one of the most important and eco-friendly multi-electron oxidants employed in the kinetic studies. The mechanism of oxidation by this multivalent oxidant depends not only on the substrate but also on the medium used for the study.…”

Section: Introductionmentioning

confidence: 99%

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Kinetics and Mechanisms of Permanganate Oxidations of Cadaverine in Different Media

Fawzy¹

2016

AJPC

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The kinetics of oxidation of cadaverine (CAD) by permanganate ion in acidic, neutral and alkaline media has been investigated spectrophtometrically at constant ionic strengths and temperature. The reactions in different media exhibited a first order kinetics in [MnO 4-] and less than unit order dependences with respect to [CAD]. The oxidation of cadaverine showed less than unit order dependences with respect to [H + ] and [OH-] in acidic and alkaline media, respectively. Variation of ionic strengths in both acidic and alkaline media had no significant effect on the oxidation rates. The proposed oxidations mechanisms in all media involve formation of 1:1 intermediate complexes between the kinetically active species of both cadaverine and permanganate ion. The final oxidation products of cadaverine were identified as 5-aminopentanal and ammonia. The appropriate rate laws in all media were deduced. The reaction constants involved in the different steps of the mechanisms were evaluated.

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“…Permanganate ion is an efficient oxidant in acid, neutral and alkaline media [15][16][17][18][19][20][21][22][23][24][25][26][27][28] which still remains as one of the most important, eco-friendly and powerful multi-electron oxidants employed in the kinetic studies [29]. The mechanism of oxidation by this multivalent oxidant depends not only on the substrate but also on the medium used for the study.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of Electron Transfer to Manganese(VII) by Fluorene and Its Halogenated Derivatives in Neutral Organic Medium

Fawzy¹,

Jassas²,

Ahmed³

et al. 2016

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The kinetics of oxidation of fluorene (Fl) and its halogenated derivatives, namely, 2,7-dichlorofluorene (Fl-Cl), 2,7-dibromofluorene (Fl-Br) and 2,7-diiodofluorene (Fl-I), by permanganate ion in neutral organic medium in the presence of phosphate buffer solution has been investigated at a constant temperature of 25°C. The progresses of the reactions were followed spectrophotometrically. The stoichiometry of the reactions was found to be 3:4 (fluorene: permanganate). The oxidation reactions exhibited a first order dependence in [permanganate] and less than unit order dependences with respect to fluorenes concentrations. Under comparable experimental conditions, the order of the oxidation rate of the fluorene derivatives was: Fl-Cl > Fl > Fl-I > Fl-Br. The final oxidation products of fluorene derivatives were identified by GC/MS, FT-IR and chemical tools as the corresponding ketones (9H-fluorenone derivatives). The proposed oxidation mechanism involves formation of 1:1 intermediate complexes between fluorene derivatives and permanganate ion in pre-equilibrium step. The ratelaw expression was deduced. The reactions constants involved in the different steps of the mechanism were evaluated. The activation parameters associated with the second order rate constants were calculated and discussed.

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Kinetics of the Oxidative Degradation of rac-Serine by Aqueous Alkaline Permanganate

Cited by 8 publications

References 0 publications

Bottom-Up Low Molecular Weight Heparin Analysis Using Liquid Chromatography-Fourier Transform Mass Spectrometry for Extensive Characterization

Bottom-Up Low Molecular Weight Heparin Analysis Using Liquid Chromatography-Fourier Transform Mass Spectrometry for Extensive Characterization

Kinetics and Mechanisms of Permanganate Oxidations of Cadaverine in Different Media

Kinetics and Mechanism of Electron Transfer to Manganese(VII) by Fluorene and Its Halogenated Derivatives in Neutral Organic Medium

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