Synthesis of persialylated beta-cyclodextrins.
The synthesis of homogeneous hepta-antennated C-6 branched sialosyl cyclomaltoheptose derivatives (persialylated beta-cyclodextrins) has been performed in good to excellent yields, and the compounds have been fully characterized. The thioacetate N-acetylneuraminic acid derivative 6 was selectively de-S-acetylated and coupled by nucleophilic displacement in a one-pot reaction to the heptakis(chloroacetamido) beta-CDs 2 and 5, yielding multivalent sialosides 8 and 9, respectively. The thiourea-linked sialyl-CD 10 was obtained by reaction of the 4-isothiocyanatophenyl N-acetylneuraminic acid derivative 7 with the per-tert-butoxycarbonylamino beta-CD derivative 2 after suitable deprotection of the amino function.
Roy
R
R
Department of Chemistry, University of Ottawa, Ontario, Canada. rroy@science.uottawa.ca
Hernández-Mateo
F
F
Santoyo-González
F
F
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D047392:beta-Cyclodextrins; D019158:N-Acetylneuraminic Acid; C031215:betadex