In vivo Metabolism of N-Acetylhexosamine ³⁵S-Sulphate Esters

Abstract

IN a previous report¹ evidence was presented indicating that the monosulphate ester obtained as the principal product of the direct sulphation of N-acetyl-D-glucosamine with chlorosulphonic acid was identical with N-acetyl-D-glucosamine 6-O-sulphate prepared by definitive synthesis. In addition, following preliminary observations on the structure of the monosulphate ester prepared by the direct sulphation of N-acetyl-D-galactosamine¹, independent results from work on tritylation (triphenylmethylation)², and infrared spectroscopy^3,4, indicate that this material is also a 6-O-sulphate ester. Since available information suggests that N-acetyl-D-glucosamine 6-O-sulphate and N-acetyl-D-galactosamine 6-O-sulphate exist in vivo as part of the polymer chains of keratosulphate and chondroitin sulphate-C respectively^5,6, it was of interest to examine the in vivo metabolism of these N-acetylhexosamine sulphate esters.