1989Recueil des Travaux Chimiques des Pays-BasRequires access

Sucrose‐derived dialdehydes: The course of the periodate oxidation as studied by HPLC

D. de Wit, Fred van Rantwijk, L. Maat, A. P. G. Kieboom

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Abstract

Abstract Sucrose was oxidized with sodium periodate to di‐ and tetraaldehyde compounds. A fast and reliable analytical HPLC method was developed to follow the course of the reaction as a function of the amount of periodate added. Apart from the sucrose tetraaldehyde, i.e. the final oxidation product, only two out of the four possible sucrose dialdehyde products were formed: one with the glucose ring twice oxidized (GOO‐F) and one with an oxidized fructose ring (G‐FO). Both dialdehydes were formed in equal amounts when low amounts of periodate were added, whereas GOO‐F was preferentially formed when higher amounts of periodate were added. The course of the reaction is discussed in terms of internal hemiacetal formation of the sucrose dialdehydes.

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Abstract Sucrose was oxidized with sodium periodate to di‐ and tetraaldehyde compounds. A fast and reliable analytical HPLC method was developed to follow the course of the reaction as a function of the amount of periodate added. Apart from the sucrose tetraaldehyde, i.e. the final oxidation product, only two out of the four possible sucrose dialdehyde products were formed: one with the glucose ring twice oxidized (GOO‐F) and one with an oxidized fructose ring (G‐FO). Both dialdehydes were formed in equal amounts when low amounts of periodate were added, whereas GOO‐F was preferentially formed when higher amounts of periodate were added. The course of the reaction is discussed in terms of internal hemiacetal formation of the sucrose dialdehydes.

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Available abstract

Abstract Sucrose was oxidized with sodium periodate to di‐ and tetraaldehyde compounds. A fast and reliable analytical HPLC method was developed to follow the course of the reaction as a function of the amount of periodate added. Apart from the sucrose tetraaldehyde, i.e. the final oxidation product, only two out of the four possible sucrose dialdehyde products were formed: one with the glucose ring twice oxidized (GOO‐F) and one with an oxidized fructose ring (G‐FO). Both dialdehydes were formed in equal amounts when low amounts of periodate were added, whereas GOO‐F was preferentially formed when higher amounts of periodate were added. The course of the reaction is discussed in terms of internal hemiacetal formation of the sucrose dialdehydes.

Key concepts: Periodate, Sodium periodate, Chemistry, Sucrose, High-performance liquid chromatography, Fructose, Hemiacetal, Sugar

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