Di- tert -butylsilylene-directed ¦Á-selective synthesis of p -nitrophenyl T-antigen analogues

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• 作者：Tetsuro Sato ; Akihiro Imamura ; Hiromune Ando ; Hideharu Ishida and Makoto Kiso
• 关键词：Glycosylation ; p ; nitrophenyl glycoside ; Di ; tert ; butylsilylene group ; Stereoselectivity ; Endo ; α ; N ; acetylgalactosaminidase
• 刊名：Glycoconjugate Journal
• 出版年：2009
• 出版时间：January, 2009
• 年：2009
• 卷：26
• 期：1
• 页码：83-98
• 全文大小：387.4 KB

文摘

Seven analogues of p-nitrophenyl T-antigen [Galβ(1→3)GalNAcα(1→O)PNP] have been synthesized as potential substrates for elucidation of the substrate specificity of endo-α-N-acetylgalactosaminidase. These compounds, which are commercially unavailable, include: GlcNAcβ(1→3){GlcNAcβ(1→6)}GalNAcα(1→O)PNP [core 4 type], GalNAcα(1→3)GalNAcα(1→O)PNP [core 5 type], GlcNAcβ(1→6)GalNAcα(1→O)PNP [core 6 type], GalNAcα(1→6)GalNAcα(1→O)PNP [core 7 type], Galα(1→3)GalNAcα(1→O)PNP [core 8 type], Glcβ(1→3)GalNAcα(1→O)PNP and GalNAcβ(1→3)GalNAcα(1→O)PNP. The assembly of these synthetic probes was accomplished efficiently, based on di-tert-butylsilylene(DTBS)-directed α-galactosylation as a key reaction.