Three glycosyllactosides, contained in the neutral fraction of human milk oligosaccharides, were synthesised in a simple and straightforward manner through a sequence based on a chemo-enzymatic approach. Lipase catalysed regioselective 6'-O-acylation of benzyl β-lactoside, followed by the introduction of an isopropylidene group and acetylation afforded, depending on the reaction conditions, compounds 4a and 4b, which allow selective access to positions 3, 3' and 6'. Glycosylation with proper donors gave trisaccharides 6, 9 and 12.
LA FERLA, B., Lay, L., Polletti, L., Panza, L., Russo, G. (2000). Easy Chemo-Enzymatic Synthesis of Human Milk Trisaccharides from a Common Selectively Protected Lactose Building Block. JOURNAL OF CARBOHYDRATE CHEMISTRY, 19(3), 331-343 [10.1080/07328300008544082].
Easy Chemo-Enzymatic Synthesis of Human Milk Trisaccharides from a Common Selectively Protected Lactose Building Block
LA FERLA, BARBARA;
2000
Abstract
Three glycosyllactosides, contained in the neutral fraction of human milk oligosaccharides, were synthesised in a simple and straightforward manner through a sequence based on a chemo-enzymatic approach. Lipase catalysed regioselective 6'-O-acylation of benzyl β-lactoside, followed by the introduction of an isopropylidene group and acetylation afforded, depending on the reaction conditions, compounds 4a and 4b, which allow selective access to positions 3, 3' and 6'. Glycosylation with proper donors gave trisaccharides 6, 9 and 12.
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