Sato Tetsuro, Imamura Akihiro, Ando Hiromune, Ishida Hideharu, Kiso Makoto
Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
Glycoconj J. 2009 Jan;26(1):83-98. doi: 10.1007/s10719-008-9168-y. Epub 2008 Aug 16.
Seven analogues of p-nitrophenyl T-antigen [Galbeta(1-->3)GalNAcalpha(1-->O)PNP] have been synthesized as potential substrates for elucidation of the substrate specificity of endo-alpha-N-acetylgalactosaminidase. These compounds, which are commercially unavailable, include: GlcNAcbeta(1-->3){GlcNAcbeta(1-->6)}GalNAcalpha(1-->O)PNP [core 4 type], GalNAcalpha(1-->3)GalNAcalpha(1-->O)PNP [core 5 type], GlcNAcbeta(1-->6)GalNAcalpha(1-->O)PNP [core 6 type], GalNAcalpha(1-->6)GalNAcalpha(1-->O)PNP [core 7 type], Galalpha(1-->3)GalNAcalpha(1-->O)PNP [core 8 type], Glcbeta(1-->3)GalNAcalpha(1-->O)PNP and GalNAcbeta(1-->3)GalNAcalpha(1-->O)PNP. The assembly of these synthetic probes was accomplished efficiently, based on di-tert-butylsilylene(DTBS)-directed alpha-galactosylation as a key reaction.
已合成了七种对硝基苯基T抗原[Galβ(1→3)GalNAcα(1→O)PNP]类似物，作为阐明内切α-N-乙酰半乳糖胺酶底物特异性的潜在底物。这些在商业上无法获得的化合物包括：GlcNAcβ(1→3){GlcNAcβ(1→6)}GalNAcα(1→O)PNP[核心4型]、GalNAcα(1→3)GalNAcα(1→O)PNP[核心5型]、GlcNAcβ(1→6)GalNAcα(1→O)PNP[核心6型]、GalNAcα(1→6)GalNAcα(1→O)PNP[核心7型]、Galα(1→3)GalNAcα(1→O)PNP[核心8型]、Glcβ(1→3)GalNAcα(1→O)PNP和GalNAcβ(1→3)GalNAcα(1→O)PNP。基于二叔丁基甲硅烷基(DTBS)导向的α-半乳糖基化作为关键反应，高效完成了这些合成探针的组装。
