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

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

Procedure: 24 g of Raney-nickel obtained by the method described above was added to 300 g of an aqueous solution containing 100 g of 6-deoxy L-mannose in a 1-L glass autoclave with an agitator and a thermometer, to which water was added to a final reaction volume of 600 g. So as to adjust the reaction mixture to pH 7, then, calcium carbonate was added. Reaction was progressed while the temperature was retained at 50° C.; the hydrogen pressure was retained at 12 kg/cm2 (gauge pressure); the agitation speed was retained at 700 rpm. The reaction mixture was analyzed by HPLC. Consequently, 6-deoxy L-mannose was decreased to 1% in the 8-hour reaction, to produce 6-deoxy L-mannitol. reaction volume of 600 g Reaction was retained at 50° C.

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

Procedure: 24 g of Raney-nickel obtained by the method described above was added to 300 g of an aqueous solution containing 100 g of 6-deoxy L-mannose in a 1-L glass autoclave with an agitator and a thermometer, to which water was added to a final reaction volume of 600 g. So as to adjust the reaction mixture to pH 7, then, calcium carbonate was added. Reaction was progressed while the temperature was retained at 50° C.; the hydrogen pressure was retained at 12 kg/cm2 (gauge pressure); the agitation speed was retained at 700 rpm. The reaction mixture was analyzed by HPLC. Consequently, 6-deoxy L-mannose was decreased to 1% in the 8-hour reaction, to produce 6-deoxy L-mannitol. reaction volume of 600 g Reaction was retained at 50° C.

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

Procedure: 24 g of Raney-nickel obtained by the method described above was added to 300 g of an aqueous solution containing 100 g of 6-deoxy L-mannose in a 1-L glass autoclave with an agitator and a thermometer, to which water was added to a final reaction volume of 600 g. So as to adjust the reaction mixture to pH 7, then, calcium carbonate was added. Reaction was progressed while the temperature was retained at 50° C.; the hydrogen pressure was retained at 12 kg/cm2 (gauge pressure); the agitation speed was retained at 700 rpm. The reaction mixture was analyzed by HPLC. Consequently, 6-deoxy L-mannose was decreased to 1% in the 8-hour reaction, to produce 6-deoxy L-mannitol. reaction volume of 600 g Reaction was retained at 50° C.

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

Procedure: 6-Deoxy L-mannitol can readily be produced via chemical reduction of 6-deoxy L-mannose. At a productivity close to 99%, 6-deoxy L-mannose is completely converted to 6-deoxy L-mannitol. When the initial concentrations of 6-deoxy L-mannitol were 3%, 4% and 5%, almost 90%, 70% and 65%, respectively of 6-deoxy L-mannitol produced 6-deoxy L-fructose and 1-deoxy L-fructose, using the washed bacterial cell reaction.

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

Procedure: In the presence of the Raney-nickel catalyst, L-rhamnose (10 w/v %) was completely reduced at a temperature of 50° C. and a pressure of 1.2 MPa, to produce 6-deoxy L-mannitol. Using the resulting 6-deoxy L-mannitol as a substrate, 6-deoxy L-fructose was produced. A freshly separated Enterobacter sp. 230S was used for selectively oxidizing the carbon in 6-deoxy L-mannitol at position 2 to prepare 6-deoxy L-fructose. The microorganism was cultured in a mineral salt-added culture medium supplemented with D-sorbitol (0.8 w/v %) and glycerol (0.2 w/v %) under agitation at a temperature of 30° C. and 300 rpm, for 24 hours. The culture was centrifuged at 12,000 rpm for 30 minutes, to harvest the bacterial cells, which were then washed twice with 50 mM Tris-HCl buffer (pH 10). The washed bacterial cells were suspended in the same buffer for use in converting 6-deoxy L-mannitol to 6-deoxy L-fructose. The reaction was done in various substrate concentrations in a 5-liter bioreactor (ABLE DPL-2, Japan), using the bacterial cells of OD600=40, a handling volume of 0.5 liter, an agitation speed of 200 rpm, an air flow rate of 0.2 liters/min and a temperature of 30° C. was completely reduced at a temperature of 50° C.