Stoichiometric C6-oxidation of hyaluronic acid by oxoammonium salt TEMPO⁺Cl⁻ in an aqueous alkaline medium

Irina Yu Ponedel'kina; Elvira A Khaibrakhmanova; Tatyana V Tyumkina; Irina V Romadova; Victor N Odinokov

doi:10.1016/j.carbpol.2015.04.054

Stoichiometric C6-oxidation of hyaluronic acid by oxoammonium salt TEMPO⁺Cl⁻ in an aqueous alkaline medium

Carbohydr Polym. 2015 Oct 5:130:69-76. doi: 10.1016/j.carbpol.2015.04.054. Epub 2015 May 1.

Authors

Irina Yu Ponedel'kina¹, Elvira A Khaibrakhmanova², Tatyana V Tyumkina², Irina V Romadova², Victor N Odinokov²

Affiliations

¹ Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Ufa 450075, Russian Federation. Electronic address: ponedelkina@rambler.ru.
² Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Ufa 450075, Russian Federation.

PMID: 26076602
DOI: 10.1016/j.carbpol.2015.04.054

Abstract

This paper reports the selective oxidation of hyaluronic acid (HA) by stoichiometric quantity of 2,2,6,6-tetramethylpiperidine-1-oxoammonium chloride (TEMPO(+)) in aqueous alkaline medium. High efficiency of the HA oxidation and quantitative yield of carboxy-HA per starting TEMPO(+), as well as unusual behavior of the oxidation system generating an oxygen upon alkali-induced oxoammonium chloride decomposition are demonstrated. The scheme for HA oxidation involving both TEMPO(+) and oxygen produced upon the TEMPO(+)Cl(-) decomposition and/or air oxygen is proposed. For comparison, the data on stoichiometric oxidation of such substrates as dermatan sulfate, water-soluble potato starch, methyl 2-acetamido-2-deoxy-β-d-glucopyranoside and ethanol are presented.

Keywords: 2,2,6,6-Tetramethylpiperidine-1-oxoammonium chloride; 2,2,6,6-Tetramethylpiperidine-1-oxyl (CID 2724126); Hyaluronic acid; Hyaluronic acid (CID 3084049); Hydroxylamine TEMPOH; Oxidation; Radical TEMPO.

Publication types

Research Support, Non-U.S. Gov't