Water → HCID 86747744, compound

HRID 1463773Notes

Reaction equation

HRID 1463773 reaction equation
O=[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].[NH2:13][C@H:14]([C:19]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][C:24]([OH:26])=[O:25])=[O:20])[C@H:15]([CH2:17][CH3:18])[CH3:16].C([O-])(O)=O.[Na+].O>CO>[CH2:2]([NH:13][C@H:14]([C:19]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][C:24]([OH:26])=[O:25])=[O:20])[C@H:15]([CH2:17][CH3:18])[CH3:16])[C:3]1([O:12][CH2:11][C@@H:9]([OH:10])[C@@H:7]([OH:8])[C@@H:5]1[OH:6])[OH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516892Sodium BicarbonateHCID 44298592L-Isoleucyl-L-aspartic acid

Product 1

HCID 86747744HCID 86747744, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30 g of anhydrous D-glucose were dissolved together with 3 g of isoleucyl-aspartic acid in 1.2 l of methanol, and 200 mg of NaHCO3 were added. The mixture was subsequently heated under reflux for 2 hours. The water which had formed was then removed by distillation with butanol, and the reaction mixture was diluted with methanol and again heated for 2 hours. After completion of the reaction, solvent was removed from the solution in vacuo, and the residue, in 300 ml of water, was applied to a 600 ml-capacity chromatography column (diameter 5 cm) packed with QAE-®Sephadex A-25. Whereas the excess glucose was located in the fore-run, it was possible to obtain selectively N-(1-deoxyfructopyranos-1-yl)-isoleucylaspartic acid using an acetic acid gradient (0 to 0.5 molar). These eluates from the column were collected and freeze-dried.

Workup

  1. additionwere added
  2. temperatureThe mixture was subsequently heated
  3. temperatureunder reflux for 2 hours
  4. customwas then removed by distillation with butanol
  5. additionthe reaction mixture was diluted with methanol
  6. temperatureagain heated for 2 hours
  7. customAfter completion of the reaction, solvent
  8. customwas removed from the solution in vacuo

Sources & evidence

ORD record
ord-7d8e44b7c599403a98b3bb3d0633274f
Source dataset
uspto-grants-1994_04
Patent number
US05302582

Reaction notes

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