Di-tert-butylsilylene-directed alpha-selective synthesis of p-nitrophenyl T-antigen analogues.
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.
Sato
Tetsuro
T
Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
Imamura
Akihiro
A
Ando
Hiromune
H
Ishida
Hideharu
H
Kiso
Makoto
M
D000941:Antigens / Q000737:chemistry* / Q000276:immunology; D002073:Butanes / Q000737:chemistry* / Q000276:immunology; D009596:Nitrophenols / Q000138:chemical synthesis* / Q000276:immunology; D012821:Silanes / Q000737:chemistry* / Q000276:immunology; D013601:T-Lymphocytes / Q000276:immunology*
D000941:Antigens; D002073:Butanes; D009596:Nitrophenols; D012821:Silanes; C512229:di-tert-butylsilylene