(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → D-(-)-Fructose

HRID 1729584Notes

Reaction equation

HRID 1729584 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[O:11]=[CH:12][C@@H:13]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[OH:14]>>[O:11]=[CH:12][C@@H:13]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[OH:14].[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:12][OH:11])[OH:10])[OH:8])[OH:6])=[O:4]

Participants

4

Conditions

Temperature
70 °C

Procedure

Streptomyces olivaceus, strain NRRL B-3583, is cultivated in a nutrient medium containing 0.7% xylose, 0.3% dextrose, 0.5% beef extract, 0.25% yeast extract, 1.0% peptone, 0.5% NaCl, 0.05% MgSO4.7H2O and 0.024% CoCl2.6H2O. The fermentation is allowed to proceed at 28° C. for 24 hours. A 2% (weight per volume) solution of a cationic polyelectrolyte is added to the fermentation broth in amounts equivalent to 0.05% (weight per volume) of the dry flocculant. The broth is briefly agitated to promote aggregation of the cells. Agitation is then stopped and sedimentation of the flocculated cells is allowed to proceed. The cell aggregates are harvested in a manner analogous to that described in Example 1. The flocculated cells are dried at 60° C. for 24 hours before subjecting the dried cell mass to gentle mechanical crushing action to reduce to particle sizes suitable for column operation. The crushed cell material is poured into a jacketed column partially filled with a 1.0 M glucose solution. The packed column is heated to 70° C. and a 1.0 M glucose solution containing 0.04 M MgCl2.6H2O adjusted to pH 8 is passed through the column to give conversion of glucose to fructose.

Workup

  1. extractionextract
  2. extraction0.25% yeast extract
  3. additionA 2% (weight per volume) solution of a cationic polyelectrolyte is added to the fermentation broth in amounts equivalent to 0.05% (weight per volume) of the dry flocculant
  4. customThe flocculated cells are dried at 60° C. for 24 hours
  5. additionThe crushed cell material is poured into a jacketed column
  6. additionpartially filled with a 1.0 M glucose solution
  7. additiona 1.0 M glucose solution containing 0.04 M MgCl2.6H2O

Sources & evidence

ORD record
ord-56ebf65babab4d0588083c2a09c2b284
Source dataset
uspto-grants-1976_11
Patent number
US03989596

Reaction notes

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