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

HRID 2058518Notes

Reaction equation

HRID 2058518 reaction equation
[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[Cl-].[Mg+2].[Cl-].[OH-].[Na+]>O>[O:8]=[CH:6][C@@H:5]([C@H:4]([C@@H:3]([C@@H:2]([CH2:1][OH:23])[OH:7])[OH:22])[OH:21])[OH:20]

Participants

5

Reactant 3

HCID 5988Sucrose2×HCID 14798Sodium HydroxideHCID 5360315Magnesium Chloride

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Food-grade sucrose, 250 g was dissolved in 250 ml of water and magnesium chloride was added to a concentration of 0.005 M. The pH was adjusted to 6.5 and maintained at this value by the addition of 0.5 N sodium hydroxide solution was needed. To the sucrose solution was added 7500 units of fructosyl transferase enzyme preparation, obtained as in Example 1, and 5000 units of glucose isomerase enzyme preparation, obtained as described by Cory, U.S. Pat. No. 4,077,842. After the mixture had been stirred at 55° C. for 24 hours, the enzyme reaction was stopped by placing the material in a boiling water bath for 10 minutes. The resulting syrup was then analyzed by high pressure liquid chromatography. The results of two different runs using different batches of enzymes are given in Table I.

Workup

  1. custom7500 units of fructosyl transferase enzyme preparation

Sources & evidence

ORD record
ord-a76a2f7f0471469bb3b42782150a1faa
Source dataset
uspto-grants-1982_03
Patent number
US04317880

Reaction notes

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