A C-glycoside mimetic of L-galactose 1-diphosphate, a potential ligand of GDP-L-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated L-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin.
LA FERLA, B., Russo, L., Airoldi, C., Nicotra, F. (2009). Solid-phase supported mimic of GDP-l-galactose. TETRAHEDRON-ASYMMETRY, 20(6-8), 744-745 [10.1016/j.tetasy.2009.03.005].
Solid-phase supported mimic of GDP-l-galactose
LA FERLA, BARBARA;RUSSO, LAURA;AIROLDI, CRISTINA;NICOTRA, FRANCESCO
2009
Abstract
A C-glycoside mimetic of L-galactose 1-diphosphate, a potential ligand of GDP-L-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated L-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin.
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