An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4′ OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.

Prosperi, D., Panza, L., Haltrich, D., Nonini, M., Riva, S. (2003). The synthesis of allolactose from amygdalin. JOURNAL OF CARBOHYDRATE CHEMISTRY, 22(5), 267-274 [10.1081/CAR-120023469].

The synthesis of allolactose from amygdalin

PROSPERI, DAVIDE;
2003

Abstract

An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4′ OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.
Articolo in rivista - Articolo scientifico
Organic synthesis; enzyme reactions; carbohydrates
English
2003
22
5
267
274
none
Prosperi, D., Panza, L., Haltrich, D., Nonini, M., Riva, S. (2003). The synthesis of allolactose from amygdalin. JOURNAL OF CARBOHYDRATE CHEMISTRY, 22(5), 267-274 [10.1081/CAR-120023469].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/24681
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