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 beta-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.

Easy chemo-enzymatic synthesis of human milk trisaccharides from a common selectively protected lactose building block / B. La Ferla, L. Lay, L. Poletti, G. Russo, L. Panza. - In: JOURNAL OF CARBOHYDRATE CHEMISTRY. - ISSN 0732-8303. - 19:3(2000), pp. 331-343.

Easy chemo-enzymatic synthesis of human milk trisaccharides from a common selectively protected lactose building block

L. Lay;L. Poletti;G. Russo;
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 beta-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.
Settore CHIM/06 - Chimica Organica
JOURNAL OF CARBOHYDRATE CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/188280
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