Fucose analogue

Hanaya, T, Yasuda, K, Yamamoto, H, Yamamoto, H, Stereoselectivity in the preparation of 5,6-dideoxy-5-dimethoxyphosphinyl-D- and -L-hexofuranoses, and an efficient synthesis of 5,6-dideoxy-5-hydroxyphosphinyl-L-galactopyranose (a P-in-the-ring L-fucose analogue). Bull. Chem. Soc. Jpn., 66, 2315-2322, 1993. 

Short syntheses of L-fucose analogues have been achieved (3 enzymatic steps) by aldol condensation of DHAP with various a-hydroxyaldehyde derivatives (using L-fuculose phosphate aldolase), followed by phosphate hydrolysis (alkaline phosphatase) and subsequent ketol isomerization (L-fucose isomerase). Selective C-labelling of thymidine in all positions of the 2 -deoxyribose ring has been achieved using an aldolase-catalysed reaction with appropriately C-labelled DHAP/acetaldehyde substrates. The labelled sugar was then converted... 

Scheme 2.2.5.12 Short enzymatic synthesis of L-fucose and hydrophobic analogues by aldolization-ketol isomerization, including kinetic resolution of racemic aldehyde precursors.

A. Hasegawa, T. Ando, M. Kato, H. Ishida, and M. Kiso, Synthesis of deoxy-L-fucose-containing sialy Lewis X ganglioside analogues, Carbohydr. Res. 257 67 (1994). 

Disaccharides analogous to isomaltulose, but containing other sugars in place of ot-D-glucose, can be obtained by similar bioconversions from different disaccharides.234 Sucrose analogues (galactose-fructose, xylose-fructose, fucose-fructose) have also been prepared by isomerization, catalyzed by an engineered fructosyltransferase.235,236... 

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