Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.
Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.
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DOI：
10.1021/ja809554x
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发表时间：
2009-04-29
影响因子：
15
通讯作者：
Danishefsky SJ
中科院分区：
文献类型：
--
作者：
Nagorny P;Fasching B;Li X;Chen G;Aussedat B;Danishefsky SJ
本文描述了在人类糖蛋白激素中发现的富含唾液酸的双天线n链聚糖的高度聚合合成，以及它在合成人类促卵泡激素(hFSH) β结构域衍生片段中的应用。该合成突出了使用sina_自由基糖苷化方案同时安装十二糖的双天线侧链，以及使用糖化学以有效的方式构建四糖核心。根据Lansbury天冬氨酸化方案，将合成的多糖用于制备hFSH β-亚基20-27aa糖基化结构域。将制备的含20-27aa结构域的n -链十二糖纳入β-hFSH亚基的策略在模型系统中得到了验证，该模型系统提供了在7和24位被壳聚糖功能化的受保护的β-hFSH亚基。
A highly convergent synthesis of the sialic acid rich biantennary N-linked glycan found in human glycoprotein hormones, and its use in the synthesis of a fragment derived from the β-domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinaÿ radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20–27aa domain of β-subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20–27aa domain into β-hFSH subunit was validated in the context of a model system providing, protected β-hFSH subunit functionalized with chitobiose at positions 7 and 24.
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影响因子：
4.3
作者：
Danishefsky, SJ;Hu, S;Seeberger, PH
通讯作者：
Seeberger, PH
影响因子：
16.6
作者：
Haase, Christian;Rohde, Heike;Seitz, Oliver
通讯作者：
Seitz, Oliver
影响因子：
15
作者：
Brik, A;Yang, YY;Wong, CH
通讯作者：
Wong, CH
影响因子：
1.8
作者：
Iserloh, U;Dudkin, V;Danishefsky, SJ
通讯作者：
Danishefsky, SJ
影响因子：
56.9
作者：
DAWSON, PE;MUIR, TW;KENT, SBH
通讯作者：
KENT, SBH