Dehydration of deoxymorphol inofructose under acidic conditions and colorimetric estimation of the products

Rao, Pragna and Kumudam, Malati and Pattabiraman, TN (1992) Dehydration of deoxymorphol inofructose under acidic conditions and colorimetric estimation of the products. Biochemical Archives, 8. pp. 239-245. ISSN 0749-5331

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Abstract

Deoxymorpholinofructose (DMF), a synthetic ketamine was subjected to treatment with 75 % sulfuric acid, 50 % sulfuric acid and 0.66 N oxalic acid in presence of heat. Products formed were analyzed by ultraviolet spectrophotometry and based on the nature of the chromogen formed by condensation with phenols. While DFM underwent dehydration in sulfuric acid media , the ketamine link was not found to be cleaved to any significant extent. Potential yield of hydroxymethy 1 furaldehyde based on chromogen formation with phenol and thiobarbituric acid in 75 % and 50 % sulfuric acid were 1.0 % and 4.0 % respectively . On the other hand , in oxalic acid medium , dehydration of DMF and cleavage of C-N bond were facile , leading to 57 % yield of hydroxymethy 1 furaldehyde. 1-Deoxy 1- morpholinofructose (DFM) a synthetic ketamine is used as standard in the estimation of glycated proteins (1). This compund as well as other amino derivatives of fructose are reported to undergo dehydration and cleavage to form hydroxymethy 1 furaldehyde (HMF) under mild acid conditions on heating (2,3). Glycated proteins answer conventional phenol-sulfuric acid reaction in which the chromogen formation is based on formation of furaldehyde derivatives (4,5). Preliminary studies however indicated that DMF did not react efficiently in phenol-sulfuric acid reaction . Recently , we identified interference in this method and developed modifications to increase, the sensitivity and selectivity of phenol- sulfuric acid reaction (6,7) . In this communication , we report studies on the behaviour of DFM under strong acid conditions and the use of different phenols in estimation of this compund colorimetrically.

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