(2R,3S,4R,5S)-hexane-1,2,3,4,5-pentol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: L-Fucose (6-deoxy L-galactose) was reduced [a composition in total of 500 ml containing L-fucose at 1% and 20 ml of the Raney-nickel catalyst] to produce L-fucitol (6-deoxy L-galactitol). FIG. 59(a) shows HPLC analysis results of L-fucose before reduction and FIG. 59(b) shows HPLC analysis results of 6-deoxy D-galactitol after the reduction. The optical rotation of 6-deoxy L-galactitol was −1.7, and FIG. 60 shows 13C NMR spectrum of 6-deoxy D-galactitol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: L-Fucose (6-deoxy L-galactose) was reduced, for a microbial oxidation of the resulting L-fucitol (6-deoxy L-galactitol) with E. agglomerans 221e [the bacterial cell at OD600=30, Tris-HCl buffer (pH 8.0) of 50 mM, the substrate 6-deoxy L-galactitol at 1%] at 30° C. for 6 hours. Only 1-deoxy D-tagatose was produced. FIG. 44(a) shows the reaction mixture after reaction, while FIG. 44 (b) shows the results of HPLC analysis of the produced 1-deoxy D-tagatose. The optical rotation was +14.0. 13C NMR spectrum thereof is shown in FIG. 45.