Incubation of fu
monisin B
1 and
D-glucose in aqueous solutions resulted in the for
mation of
N-(1-deoxy-
D-fructos-1-yl) fu
monisin B
1 in addition to the previously reported
N-(carboxy
methyl) fu
monisinB
1.
N-(1-Deoxy-
D-fructos-1-yl) fu
monisin B
1 is the first stable product for
med after the A
madorirearrange
ment of the Schiff base for
med by the reaction of the pri
mary a
mine of fu
monisin B
1 andthe aldehyde group of
D-glucose.
N-(1-Deoxy-
D-fructos-1-yl) fu
monisin B
1 was synthesized by reactingfu
monisin B
1 with an excess of
D-glucose in
methanol and heating for 6 h at 64
mages/entities/deg.gif">C. It was purifiedusing C
18 and strong cation exchange solid-phase extraction cartridges and characterized by nuclear
magnetic resonance and liquid chro
matography-
mass spectro
metry. Subsequently,
N,
N-di
methylfor
ma
mide was found to be a better reaction solvent, requiring reaction for only 2-3 h at 64
mages/entities/deg.gif">C andeli
minating the for
mation of
methyl esters. Alkaline hydrolysis of
N-(1-deoxy-
D-fructos-1-yl) fu
monisinB
1 gave a
mixture of hydrolyzed fu
monisin B
1 and hydrolyzed
N-(carboxy
methyl) fu
monisin B
1.Keywords: Fu
monisins;
N-(1-deoxy-
D-fructos-1-yl) fu
monisin B
1; A
madori rearrange
ment; LC-MS
