用于α-L-艾杜糖醛酸糖苷2-硫酸化的短合成序列。
Short synthetic sequence for 2-sulfation of alpha-L-iduronate glycosides.
作者信息
Blanchard Sophie, Turecek Frantisek, Gelb Michael H
机构信息
Department of Chemistry, University of Washington, Seattle, WA 98195, USA.
出版信息
Carbohydr Res. 2009 May 26;344(8):1032-3. doi: 10.1016/j.carres.2009.03.012. Epub 2009 Mar 20.
Abstract
Hunter syndrome (mucopolysaccharidosis-II) is caused by deficiency of the lysosomal enzyme iduronate-2-sulfatase. The assay of this sulfatase requires the use of alpha-L-iduronate glycosides containing a sulfate at the 2-position. We report a simple, three-step procedure for the introduction of sulfate at the 2-position starting with the methyl ester of alpha-L-iduronate glycosides. The procedure involves protection of the 2- and 4-hydroxyl groups of the iduronate moiety as the dibutyl stannylene acetal, selective sulfation with sulfur trioxide-trimethylamine, and deprotection of the methyl ester to afford the desired 2-sulfate in 61% overall yield.
摘要
亨特综合征（黏多糖贮积症II型）是由溶酶体酶艾杜糖醛酸-2-硫酸酯酶缺乏引起的。该硫酸酯酶的测定需要使用在2位含有硫酸酯的α-L-艾杜糖醛酸糖苷。我们报道了一种简单的三步方法，以α-L-艾杜糖醛酸糖苷的甲酯为起始原料，在2位引入硫酸酯。该方法包括将艾杜糖醛酸部分的2-和4-羟基保护为二丁基亚锡缩醛，用三氧化硫-三甲胺进行选择性硫酸化，以及甲酯的脱保护，以61%的总收率得到所需的2-硫酸酯。
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本文引用的文献
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Tandem mass spectrometry for the direct assay of enzymes in dried blood spots: application to newborn screening for mucopolysaccharidosis II (Hunter disease).串联质谱法直接检测干血斑中的酶：在黏多糖贮积症II型（亨特氏病）新生儿筛查中的应用
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