Chemical synthesis of N-acetylgalactosamine-αI-phosphate 6-O-sulphate, N-acetylchondrosine sulphate and UDP-N-acetylgalactosamine6-O-sulphate

A.H. Olavesen , E.A. Davidson
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引用次数: 2

Abstract

The 6-O-sulphates of 2-acetamido-2-deoxy-α-D-galactose I-phosphate (N-acetylgalactosamine-αI-phoshate), O-(β-D-glucopyranosyluronic acid)-(I→3)-2-acetamido-2-deoxy-D-galactase (N-acetylchondrosine) and UDP-2-acetamido-2-deoxy-α-D-galactose (UDP-N-acetylgalactosamine) were synthesized using triethylamine-N-sulphonic acid as sulphating agent. The products of the reaction were purified by fractionation on ECTEOLA-cellulose and converted to the barium salts by passage through the barium form of a cation-exchange resin. Evidence for the homogeneity of the sulphates was provided by chemical analysis, paper chromatography, electrophoresis, colorimetric assay and infrared spectra. Proof for the position of the sulphate group on the primary hydroxyl of the N-acetylhexosamines was provided by periodate consumption studies and the detection of glycolaldehyde sulphate as an end product of periodate oxidation.

n -乙酰半乳糖胺-α i -磷酸6- o硫酸盐、n -乙酰硫酸软骨素和udp - n -乙酰半乳糖胺6- o硫酸盐的化学合成
以三乙胺- n -磺酸为磺化剂,合成了2-乙酰氨基-2-脱氧-α- d -半乳糖-磷酸(n -乙酰半乳糖-α- I-磷酸)、O-(β- d -葡萄糖醛酸)-(I→3)-2-乙酰氨基-2-脱氧-d -半乳糖酶(n -乙酰软糖)和udp -2-乙酰氨基-2-脱氧-α- d -半乳糖(udp - n -乙酰半乳糖)的6-O硫酸盐。反应产物在ecteola -纤维素上通过分馏纯化,并通过阳离子交换树脂的钡形式转化为钡盐。化学分析、纸层析、电泳、比色测定和红外光谱提供了硫酸盐均匀性的证据。高碘酸盐消耗研究和作为高碘酸盐氧化的最终产物的硫酸乙醇醛的检测提供了硫酸盐基团在n -乙酰己糖胺的伯羟基上的位置的证据。
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