Synthesis of Oligosaccharide Components of the Outer Core Domain of P. aeruginosa Lipopolysaccharide Using a Multifunctional Hydroquinone-Derived Reducing-End Capping Group.

Synthesis of Oligosaccharide Components of the Outer Core Domain of P. aeruginosa Lipopolysaccharide Using a Multifunctional Hydroquinone-Derived Reducing-End Capping Group.
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DOI:
10.1021/acs.orglett.7b03590
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发表时间:
2018-01-19
期刊:
影响因子:
5.2
通讯作者:
Sucheck SJ
Sucheck SJ
中科院分区:
化学1区
文献类型:
--
作者:
Vartak A;Hefny FM;Sucheck SJ

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本文报道了利用新型对苯二酚基还原端盖基从铜绿假单胞菌脂多糖(LPS)的外核结构域合成三糖(糖型I和糖型II共有)和四糖(糖型I共有)。该多功能旋盖基团被用作纯化手柄,对低聚糖合成中的许多常见转化具有稳定性。通过tbdps保护的对苯二酚(TPH)在还原端进入外核LPS抗原将有助于聚糖阵列和治疗性糖缀合物的合成
The synthesis of a trisaccharide (common to glycoform I and II) and a tetrasaccharide (common to glycoform I) from the outer core domain of Pseudomonas aeruginosa lipopolysaccharide (LPS) using a novel hydroquinone-based reducingend capping group is reported. This multifunctional capping group was utilized as purification handle and was stable toward many common transformations in oligosaccharide synthesis. The access to outer-core LPS antigens with a TBDPS-protected hydroquinone (TPH) at the reducing end will be useful for glycan array and therapeutic glycoconjugate synthesis
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