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.
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