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Glycotentacles: Synthesis of Cyclic Glycopeptides, Toward a Tailored Blocker of Influenza Virus Hemagglutinin
Author(s) -
Ohta Takashi,
Miura Nobuaki,
Fujitani Naoki,
Nakajima Fumio,
Niikura Kenichi,
Sadamoto Reiko,
Guo ChaoTan,
Suzuki Takashi,
Suzuki Yasuo,
Monde Kenji,
Nishimura ShinIchiro
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351640
Subject(s) - glycopeptide , hemagglutinin (influenza) , peptide , hemagglutination , amino acid , chemistry , inhibitory postsynaptic potential , virus , cyclic peptide , sequence (biology) , peptide sequence , hemagglutination assay , scaffold , biochemistry , stereochemistry , virology , biology , medicine , antibiotics , neuroscience , gene , biomedical engineering , titer
Blocking flu : A cyclic peptide, cyclo(Ser‐Gly‐Gly‐Gln‐Ser‐His‐Asp) 3 , is an excellent scaffold for the synthesis of a cyclic glycopeptide carrying GM3 oligosaccharides with a potent inhibitory effect on the hemagglutination induced by the influenza virus. Tridentate binding of the gylcopeptide is shown to produce a much greater inhibitory effect than di‐ or monodentate binding. The shape of the glycopeptide protein scaffold, which is determined by the amino acid sequence employed, is also found to be significant in determining the inhibitory activity.