摘要
目的合成一种新的组装寡糖的“building block”,进一步扩展寡糖的化学合成工艺。方法通过对D-葡萄糖环上各羟基进行选择性保护-脱保护和基团转化,经9步反应把2-OH转换成-N3,3-OH转换成-SH,制备对甲苯基-2-叠氮基-3-巯基-4.6-O-苯亚甲基-1,3-二硫-β-D-吡喃甘露糖苷9。结果由D-葡萄糖苷3-OH转换成新的定向偶联活性基团3-SH,得到含硫的寡糖“building block”(SJ-9),9步合成的总收率为10%。结论所合成的“building block”9将能进一步扩充寡聚糖糖库中以硫苷键结合的寡糖族,有利于筛选潜在的寡糖药物。
Objective To synthesize 2-azido-3-thiol-β- D-mannopyranoside, a novel ＂building block＂ of assembly of oligosaccharides, for expending the usage of chemosynthesis technique of oligosaccharides. Methods Selective protection-deprotection strategy was used to treat hydroxyls of D-glucose. Through 9 steps, 2-OH was converted into -N3 and 3-OH into 3-SH, giving P-methylphenyl-2-azido-3-thiol- 4,6-O-benzyl-idene-1,3-dithio-β-D-mannopyranoside 9. Ftosults The novel thiosugar derivative 9 （SJ-9）, namely ＂building block＂, was synthesized by an overall yield of 10 %. Conclusion The novel ＂building block＂, thiosugar derivative 9 （SJ-9）, was successfully synthesized, which could extend the family of thioglyeosides in the assembly of ollgosaccharides and glycoconjugates, and could be used to screen oligosaccharides in the therapeutic applications.
出处
《广东医学院学报》
2007年第1期9-14,共6页
Journal of Guangdong Medical College
基金
广东省自然科学基金资助项目(No5011588)
关键词
寡糖
合成
building
BLOCK
硫代糖
2-azido-3-thiol-13-D-mannopyranoside
oligosaccharide
synthesis
thiosugar
