Silyl Linker-based Approach to the Solid-phase Synthesis of Fmoc Glycopeptide Thioesters
Silyl Linker-based Approach to the Solid-phase Synthesis of Fmoc Glycopeptide Thioesters
复制标题
基于甲硅烷基连接体的 Fmoc 糖肽硫酯的固相合成方法
DOI：
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发表时间：
2002
期刊：
影响因子：
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通讯作者：
Y. Nakahara
中科院分区：
文献类型：
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作者：
A. Ishii;H. Hojo;Y. Nakahara;Yukishige Ito;Y. Nakahara
本文报道了Fmoc（糖）肽硫酯的高效固相合成。Fmoc·Ser·OAll和Fmoc·Thr·OAll通过硅醚连接键与树脂键合，在Pd（0）催化下脱烯丙基化，在DCC/HOBt活化下与苯硫酚、苄硫醇和3-巯基丙酸乙酯缩合。通过用CsF-AcOH处理或通过酸水解从树脂释放硫酯。通过合成涉及N→C和C→N肽延伸的更复杂的（糖）肽硫酯25、26和27，进一步证明了这种甲硅烷基接头策略的有效性。
An efficient solid-phase synthesis of Fmoc (glyco)peptide thioesters is described. Fmoc·Ser·OAll and Fmoc·Thr·OAll bound to resin with a silyl ether linker were deallylated by Pd(0) catalysis and condensed with thiophenol, benzyl mercaptane, and ethyl 3-mercaptopropionate by activation with DCC/HOBt. The thioesters were released from the resin either by treatment with CsF-AcOH or by acidic hydrolysis. The effectiveness of this silyl linker strategy is further demonstrated by the synthesis of more complex (glyco)peptide thioesters 25, 26 and 27 involving N→C and C→N peptide elongation.
影响因子：
56.9
作者：
DAWSON, PE;MUIR, TW;KENT, SBH
通讯作者：
KENT, SBH