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

HRID 2354519Notes

Reaction equation

HRID 2354519 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.COS([O-])(=O)=O>O.S(=O)(=O)(O)O>[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]

Participants

6

Reactant 3

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 4694097Methyl sulfate(1-)

Product 1

HCID 440995(+)-Lactose

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

100 mmol/l of glucose, 20 mmol/l of galactose and 2 mg/ml of galactosidase are incubated at 35° C. in a mixture of water and MMIm MeSO4 for 24 h. The reaction is stopped by boiling for 10 minutes at 100° C., the reaction solution is filtered (Minisart RC 4 Sartorius injection filter) and the concentration of the reaction components at this time is determined chromatographically (Aminex HPX-87H cation exchange column from BioRad with corresponding preparatory column, 0.006 M sulphuric acid as eluent with a flux of 0.8 ml/min and a column temperature of 65° C. Detection is accomplished using UV at 208 nm and using the refractive index).

Workup

  1. filtrationthe reaction solution is filtered
  2. filtration(Minisart RC 4 Sartorius injection filter)
  3. customthe concentration of the reaction components at this time
  4. customa column temperature of 65° C

Sources & evidence

ORD record
ord-e15886c04150457191d7c2d5e55feede
Source dataset
uspto-grants-2010_07
Patent number
US07754462B2

Reaction notes

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