Tetrahedron Letters p. 6591 - 6593 (1999)
Update date:2022-08-05
Topics: Chemoenzymatic synthesis Glycosylation Oligosaccharide
Yasukochi, Takashi
Fukase, Koichi
Kusumoto, Shoichi
3-Nitro-2-pyridyl (3NPy) glycosides, which act as versatile glycosyl donors in enzymatic transglycosylation, can also be chemically activated. Chemical glycosylation with protected 3NPy glycosides was readily effected at -20°C by using TMSOTf as a catalyst to afford the desired glycosides in good yields. A trisaccharide serine conjugate Gal(β1-3)Gal(β1-4)Xylβ-Ser was synthesized by combined use of enzymatic and chemical glycosylations. The trisaccharide 3NPy glycoside was prepared by stepwise transglycosylation of a Gal-3NPy donor to a Xyl-3NPy acceptor by using a β-galactosidase. After protection of the free hydroxy groups of the trisaccharide by acetylation, the 3NPy glycoside was then subjected to chemical glycosylation of a serine residue to afford the trisaccharide serine conjugate.
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