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1,5‐Lactamized Sialyl Acceptors for Various Disialoside Syntheses: Novel Method for the Synthesis of Glycan Portions of Hp‐s6 and HLG‐2 Gangliosides
Author(s) -
Ando Hiromune,
Koike Yusuke,
Koizumi Sachiko,
Ishida Hideharu,
Kiso Makoto
Publication year - 2005
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.200501608
Subject(s) - glycan , chemistry , sialic acid , n acetylneuraminic acid , reactivity (psychology) , biochemistry , glycoprotein , pathology , medicine , alternative medicine
A dramatic enhancement of the reactivity of the C4‐ and C8‐hydroxy groups of sialic acid has been demonstrated by 1,5‐lactam bridging. Sialyl‐α(2→4)sialoside and sialyl‐α(2→8)sialoside were made available in high yields through direct sialylation (see scheme). Furthermore, the glycan parts of the new gangliosides Hp‐s6 and HLG‐2 were synthesized for the first time.