D-(-)-Fructose → D-(-)-Fructose

HRID 1534323Notes

Reaction equation

HRID 1534323 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:13]=[CH:14][C@@H:15]([C@H:17]([C@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])O.[OH:25][CH2:26][C:27]([C@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[OH:30])=[O:28]>>[OH:1][CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([O:8][C@@H:23]2[O:24][C@H:15]([CH2:14][OH:13])[C@H:17]([OH:18])[C@H:19]([OH:20])[C@H:21]2[OH:22])[C@H:5]([OH:6])[C@H:3]1[OH:4].[OH:25][CH2:26][C:27]([C@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[OH:30])=[O:28]

Participants

5

Reactant 3

HCID 5984D-(-)-FructoseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 2

HCID 5984D-(-)-FructoseHCID 440995(+)-Lactose

Procedure

The reaction mixture was subjected to purification by the column chromatography using active charcoal. Thus, the column was loaded with the oligosaccharide and elution of the adsorbed oligosaccharide was conducted by successively increasing the concentration of ethyl alcohol eluant. The eluate fraction obtained with 15% ethyl alcohol as the eluant was concentrated by evaporation and subjected to desalting and decoloration using active charcoal and an ion exchange resin followed by freeze-drying to give 2.7 g of the transglycosidation product B having a purity of 98%. A portion of this transglycosidation product B was taken and subjected to the fractionating high-performance liquid chromatography to give a chromatogram having a single peak as is shown in FIG. 3. Hydrolysis of the transglycosidation product B indicated that it was composed of glucose, galactose and fructose. The enzymolytic hydrolysis of the same with the β-fructofuranosidase gave lactose and fructose in equal molar amounts. FIG. 4 shows a 13C-NMR spectrum of the transglycosidation product B.

Workup

  1. customThe reaction mixture was subjected to purification by the column chromatography
  2. washThus, the column was loaded with the oligosaccharide and elution of the adsorbed oligosaccharide
  3. temperatureby successively increasing the concentration of ethyl alcohol eluant
  4. customThe eluate fraction obtained with 15% ethyl alcohol as the eluant
  5. concentrationwas concentrated by evaporation
  6. customby freeze-drying
  7. customto give 2.7 g of the transglycosidation product B
  8. customto give a chromatogram
  9. customThe enzymolytic hydrolysis of the same with the β-fructofuranosidase

Sources & evidence

ORD record
ord-5fe0f94aa63346a38b2f37b7d6e85409
Source dataset
uspto-grants-1992_02
Patent number
US05089401

Reaction notes

Loading…