caa a22 4500 465734480 CHVBK 20180323111751.0 cr unu---uuuuu 170327e19900701xx s 000 0 eng 10.1007/BF01073378 doi (NATIONALLICENCE)springer-10.1007/BF01073378 New ganglioside analogs that inhibit influenze virus sialidase [Elektronische Daten] [Yasuo Suzuki, Katsuhiko Sato, Makoto Kiso, Akira Hasegawa] Synthetic thioglycoside-analogs of gangliosides such as Neu5Acα)2-S-6)Glcβ-(1-1)Ceramide (1) and the GM3 analog Neu5Acα(2-S-6)Galβ-(1-4)Glcβ(1-1)Ceramide (2), competitively inhibited GM3 hydrolysis by the sialidase of different subtypes of human and animal influenza viruses with an apparent Ki value of 2.8×10−6 and 1.5×10−5 M, respectively. The inhibitory activity of the ganglioside GM4 analog [Neu5Acα-(2-S-6)Galβ-(1-1)Ceramide (3)], in which the glucose of 1 was substituted by galactose, was lower than that of 1 (Ki =1.0×10−4 M). The thioglycoside-analogs (1, 2, 3) of the gangliosides were nonhydrolyzable substrates for influenza virus sialidase. The inhibitory activity of 1 to bacterial sialidases fromClostridium perfringens andArthrobacter ureafaciens was considerably lower than that to influenza virus sialidase, indicating that the structure of the active site in bacterial and influenza virus sialidase may be different and the analogs may be useful to determine the orientation of the substrate to the active site of sialidases, especially of influenza viruses. Glycoconjugate Journal AB, 1990 sialidase inhibitor nationallicence Thioglycoside-analog of ganglioside nationallicence influenza virus nationallicence Cer : ceramide nationallicence GM3 : Neu5Acα(2-3)Galβ(1-4)Glcβ(1-1)Cer nationallicence GM4 : Neu5Acα(2-3)Galβ(1-1)Cer nationallicence Suzuki Yasuo Department of Biochemistry, University of Shizuoka, School of Pharmaceutical Science, 395 Yada, 422, Shizuoka, Japan aut Sato Katsuhiko Department of Biochemistry, University of Shizuoka, School of Pharmaceutical Science, 395 Yada, 422, Shizuoka, Japan aut Kiso Makoto Department of Applied Bio-organic Chemistry, Gifu University, 501-11, Gifu, Japan aut Hasegawa Akira Department of Applied Bio-organic Chemistry, Gifu University, 501-11, Gifu, Japan aut Glycoconjugate Journal Kluwer Academic Publishers 7/4(1990-07-01), 349-356 0282-0080 7:4<349 1990 7 10719 https://doi.org/10.1007/BF01073378 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF01073378 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Suzuki Yasuo Department of Biochemistry, University of Shizuoka, School of Pharmaceutical Science, 395 Yada, 422, Shizuoka, Japan aut NATIONALLICENCE 700 1- Sato Katsuhiko Department of Biochemistry, University of Shizuoka, School of Pharmaceutical Science, 395 Yada, 422, Shizuoka, Japan aut NATIONALLICENCE 700 1- Kiso Makoto Department of Applied Bio-organic Chemistry, Gifu University, 501-11, Gifu, Japan aut NATIONALLICENCE 700 1- Hasegawa Akira Department of Applied Bio-organic Chemistry, Gifu University, 501-11, Gifu, Japan aut NATIONALLICENCE 773 0- Glycoconjugate Journal Kluwer Academic Publishers 7/4(1990-07-01), 349-356 0282-0080 7:4<349 1990 7 10719 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer