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Kinetics of Oxidation of Myo-Inositol by Potassium Periodate in Alkaline Medium†

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Kinetics of Oxidation of Myo-Inositol by Potassium Periodate in Alkaline Medium† Asian Journal of Chemistry; Vol. 24, No. 12 (2012), 5869-5872 Kinetics of Oxidation of myo-Inositol by Potassium Periodate in Alkaline Medium† 2 1,* 2 Y. LAKSHMAN KUMAR , R. VENKATA NADH and P.S. RADHAKRISHNAMURTI 1School of Biotechnology, Vignan University, Vadlamudi-522 213, India 2Department of Chemistry, Tellakula Jalayya Polisetty Somasundaram College, Guntur-522 006, India *Corresponding author: E-mail: [email protected] AJC-11780 Kinetics of oxidation of myo-inositol by potassium periodate both in alkaline and acid media were studied. The reactions were found to be first order in case of periodate in both media. In the case of base catalyzed reactions, a decrease in the rate of the reaction was observed with an increase in the concentration of substrate. An inverse fractional order with respect to substrate in alkaline shows the substrate inhibition. A positive fractional order was observed for substrate in acid catalyzed reactions. The dependence on hydrogen ions and hydroxide ions was found to be inverse fractional order. Arrhenius parameters were calculated for both the reactions conducted in acid and alkali media. Plausible mechanism is postulated based on experimental results. Key Words: Kinetics, Substrate inhibition, Inositol, Potassium periodate, Alkaline medium, Acid medium. INTRODUCTION EXPERIMENTAL myo-Inositol is a six-member carbon ring polyol that myo-Inositol, potassium periodate, perchloric acid, is synthesized by both eukaryotes and prokaryote1. Inositol potassium hydroxide, boric acid, DMSO and all other reagents occurs in animal tissues in both free and combined forms. myo- used in these experiments were of analytical reagent grade. Inositol and its various biochemical derivatives are widely The reaction kinetics was followed by iodometry. In the oxi- distributed in mammalian tissues, higher plants, fungi and some dation of inositol, one oxygen loss or two electrons transfer bacteria, where they are important in many crucial cellular per periodate molecule was observed i.e., oxidation capacity compounds, including those involved in signal transduction of oxidant was observed till the conversion of periodate into such as phosphatidylinositol phosphates and myo-inositol iodate. This was also confirmed by non oxidation of inositol phosphates2 gene expression3, auxin perception and phos- by iodate. phorus storage4,5, membrane tethering6 and oligosaccharide synthesis7. RESULTS AND DISCUSSION Oxidation of inositol was studied by different oxidants Variation of [periodate]: The oxidant periodate concen- like alkaline hexacynofrrate(III) ion in presence of Osmium tration was varied in the range of 0.00025 to 0.001 M and (VIII)8, vanadium(V) in acid medium in absence9 and presence fairly constant k1 value indicates that order with respect to 10 11 12-14 of copper (II) , periodate , periodic acid . [periodate] was unity (Tables 1 and 2). This was also confirmed Since the periodate ion is a large and negatively charged by linearity of the plots of log (a-x) versus time upto 85 % entity that is unlikely to permeate membranes passively at completion of reaction. lower temperatures, glycoinositol phospholipids at the cell Reaction orders of acid /alkali and substrate: The surface were detected by sodium periodate oxidation reaction15-17 reaction orders were determined from the slope of log k1 vs. and hence used for topological studies. In view of the biological log [variant] plots by varying the concentrations of inositol, importance of inositol and its derivatives oxidation by periodate, acid/alkali in turn while keeping all other concentrations and it was decided to study the oxidation of inositol by periodate conditions constant. in aqueous alkaline medium and for the purpose of comparison, Variation of [acid]/[alkali]: The effect of increase in reactions were also carried out in acid medium. concentration of acid/alkali on the reaction was studied at †Presented at International Conference on Global Trends in Pure and Applied Chemical Sciences, 3-4 March, 2012; Udaipur, India 5870 Kumar et al. Asian J. Chem. constant concentration of periodate and inositol at constant Lower rate of reaction in alkali medium: The rate of temperature of 35 ºC. In both cases, the rate constants decreased reaction between periodate and inositol in alkaline medium is with an increase in acid/alkali concentrations (Tables 1 and lower compared to acid medium, which can be attributed to 2), indicating inverse fractional order dependence of rate on the slow scission of substrate as well as slow cleavage of the acid/alkali. complex between oxidant and substrate. Such reports also are In the alkaline medium, the dissociative equilibria (1-3) available in the literature in the case of reaction between - 25 of the IO4 was detected and the corresponding equilibrium alcohols and periodate. Perlin and Von Rudolff reported that constants were determined at 298.2 K by Aveston18. the cleavage of complex between diols and periodate is slower - - 4- in weakly alkaline compared to that in acid medium. In addition, 2IO4 + 2OH H2I2O10 log β1 = 15.05 (1) the rate of glycol scission by periodate may be retarded as the - - 2- IO4 + OH + H2O H3IO6 log β2 = 6.21 (2) pH is raised26,27. - - 3- IO4 + 2OH H2IO6 log β3 = 8.67 (3) Variation of [inositol]: The effect of inositol concentration The distribution of all species of periodate in aqueous on the rate of reaction was studied at constant concentration of acid/alkali and periodate at 35 ºC. The k1 values increased alkaline solution can be calculated from equilibria (1-3). K1, with an increase in concentration of inositol in the case of K2 and K3 are the equilibrium constants in the above equations 1-3, respectively. In the [OH-] range used in this work the acid medium and the apparent order with respect to [inositol] 4- – was found to be positive fractional (Table-2). In the case of amount of dimer (H2I2O10 ) and IO4 species of periodate can 6- alkali medium, substrate inhibition was observed i.e., the rate be neglected. The main species of periodate are H2IO3 and 6- of the reaction decreased with an increase in the inositol and H3IO2 , which are consistent with the result calculated from Crouthamel's data19 and other recent results reported in the an inverse fractional order was found w.r.t. inositol (Table-1). literature20-22. Similar effects have been observed with hexacyanoferrate(III) 28 29 Eqs. (4) and (5) can be obtained23 from (2) and (3): of carbohydrates and ceric sulphate oxidation of alcohols . Substrate inhibition i.e., a decrease in rate of reaction with an β [OH − ]2 [H IO 3− ] = 3 IO[ − ] = ([f OH − ])[ IO − ] increase in substrate concentration can be contributed to the 2 6 1+ β [OH − ] + β [OH − ]2 4 ex 4 ex (4) 2 3 formation of periodate-inositol complex which resists oxida- − tion. The inert complexes must contain a higher proportion of 2− β2[OH ] − − − [H3IO 6 ] = − − 2 IO[ 4 ]ex = φ([ OH ])[ IO 4 ]ex (5) substrate molecules because of 1:1 complexes, which take part 1+ β2 [OH ] + β3[OH ] - in the oxidation. Here [IO4 ]ex represents the concentration of the original overall periodate ion and is approximately equal to the sum of TABLE-1 3- 2- [H2IO6 ] and [H3IO6 ]. At lower concentration of alkali (0.05 OXIDATION OF MYO-INOSITOL BY POTASSIUM 2- 3- M), the concentrations of H3IO6 and H2IO6 are 0.0003076 PERIODATE IN AN ALKALI MEDIUM 4 –1 M and 0.00018 M respectively, whereas at higher concen- Variant Concentration of variant (M) k1 × 10 (sec ) trations of alkali (0.833 M), the corresponding concentrations Periodate 0.00025 2.110 are 0.0000465 M and 0.000453387 M respectively. Hence, 0.00050 2.117 2- 0.00100 1.873 H3IO6 is the predominant species at lower concentration of – 3- OH 0.050 2.780 alkali whereas H2IO6 is the predominant species at higher 0.100 2.117 concentration of alkali. Based on such distribution, we can 2- 0.200 1.345 conclude that inositol complexes with either H3IO6 or the 0.500 1.070 3- less protonated ionic species H2IO6 . If two or more hydroxyl 0.833 0.763 groups in a polyol are in a sterically favourable arrangement Inositol 0.0005 14.821 they may displace two or more molecules, respectively, of 0.0010 12.113 water from the solvation sphere of periodate ion. In alkaline 0.0025 7.529 solution hydroxyl groups can, after losing a proton, form much 0.0125 2.662 stronger complexes. 0.0250 2.117 24 0.0500 1.340 Barker described the existence of triesters of periodate 0.1000 0.648 ion with inositol and suggested that the iodine atom is attached Temperature 35 ºC 2.117 to an ax-eq-ax sequence of oxygen atoms. The NMR spectrum 45 ºC 4.372 confirmed the suggested structure (Fig. 1). Out of the three 55 ºC 19.133 hydroxyls, one is axial hydroxyl second is equatorial and third Boric acid 0 2.117 is axial hydroxyl and these three OH's have complexed with 0.010 2.136 2- 0.025 2.536 the periodate species H3IO6 in alkaline medium. 0.050 3.234 Conditions: [Inositol] = 0.025 M; [OH –] = 0.1 M; [Pot. periodate] = 2- O 0.0005 M; Temperature = 35 ºC O3I OH OH O O Effect of addition of solvent-dimethyl sulphoxide: OH Dimethyl sulphoxide is a dipolar aprotic solvent and it has a Fig. 1. Periodate ion and inositol complex dielectric constant less than that of water. To find out the effect Vol. 24, No. 12 (2012) Kinetics of Oxidation of myo-Inositol by Potassium Periodate in Alkaline Medium 5871 of dielectric constant (D) on the rate of oxidation in acid Such observations were reported earlier by other authors in medium, the reactions have been carried out at various propor- sodium borate solution.
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