霍乱弧菌 O:139 荚膜 O-多糖的轭合物准备、下游二糖片段的合成。
Synthesis of the conjugation ready, downstream disaccharide fragment of the O-PS of Vibrio cholerae O:139.
机构信息
NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA.
出版信息
Carbohydr Res. 2011 Sep 6;346(12):1394-7. doi: 10.1016/j.carres.2011.02.011. Epub 2011 Feb 25.
Abstract
The linker-equipped disaccharide, 8-amino-3,6-dioxaoctyl 2,6-dideoxy-2-acetamido-3-O-β-D-galactopyranosyluronate-β-D-glucopyranoside (10), was synthesized in eight steps from acetobromogalactose and ethyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-1-thio-β-D-glucopyranoside. The hydroxyl group present at C-4(II) in the last intermediate, 8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosyluronate)-β-D-glucopyranoside (9), is positioned to allow further build-up of the molecule and, eventually, construction of the complete hexasaccharide. Global deprotection (9→10) was done in one step by catalytic hydrogenolysis over palladium-on-charcoal.
摘要
将 8-氨基-3,6-二氧辛基 2,6-二脱氧-2-乙酰氨基-3-O-β-D-半乳糖吡喃糖基uronate-β-D-吡喃葡萄糖苷（10）与乙缩醛半乳糖和乙基 4,6-O-亚苄基-2-脱氧-2-三氯乙酰氨基-1-硫-β-D-吡喃葡萄糖苷反应，经八步合成了带有连接子的二糖。最后一个中间体 8-叠氮-3,6-二氧辛基 4-O-苄基-6-溴-2,6-二脱氧-2-三氯乙酰氨基-3-O-（苄基 2,3-二-O-苄基-β-D-半乳糖吡喃糖基uronate）-β-D-吡喃葡萄糖苷（9）中 C-4（II）上的羟基位置使其能够进一步构建分子，并最终构建完整的六糖。通过钯炭上的催化氢化一步完成了全局脱保护（9→10）。
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