(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 13018026, compound

HRID 1447468Notes

Reaction equation

HRID 1447468 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1([C@@H](N)C([NH:22][C@H:23]2[C:30](=[O:31])[N:29]3[C@@H:24]2[CH2:25][CH2:26][CH:27]=[C:28]3[C:32]([OH:34])=[O:33])=O)C=CC=CC=1>>[NH2:22][CH:23]1[C:30](=[O:31])[N:29]2[CH:24]1[CH2:25][CH2:26][CH:27]=[C:28]2[C:32]([OH:34])=[O:33]

Participants

3

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 131712426HCID 131712426, compound2×

Product 1

HCID 13018026HCID 13018026, compound

Procedure

Clostridium acetobutylicum IFO 3346 is inoculated in 100 ml of Potato Dextrose Broth (product of DIFCO Lab.). Air in the fermentor is replaced with sterilized nitrogen gas and the fermentor is sealed. Culturing is carried out at a temperature of 30° C. for 48 hours. After the cultivation, cells are recovered, washed with physiological saline solution and suspended in 2 ml of 1/30 M potassium phosphate buffer (pH 7.0). 0.5 ml of the substrate solution prepared as in Example 5 and the cell suspension are combined and allowed to react at a temperature of 30° C. for 20 hours. The reaction is monitored as in Example 5. (-)-cis-7-[(R)-2-phenyl-2-aminoacetamido]-1-azabicyclo[4,2,0]oct-2-en-8-on-2-carboxylic acid is remained unchanged and only (+)-cis-7-[(R)-2-phenyl-2-aminoacetamido]-1-azabicyclo[4,2,0]oct-2-en-8-on-2-carboxylic acid is decreased. The amount of the decrease is 1.0 mg, producing 0.2 mg of (+)-7-amino-1-azabicyclo[4,2,0]oct-2-en-8-on-2-carboxylic acid.

Workup

  1. customthe fermentor is sealed
  2. customAfter the cultivation, cells are recovered
  3. washwashed with physiological saline solution
  4. custom0.5 ml of the substrate solution prepared as in Example 5
  5. customto react at a temperature of 30° C. for 20 hours

Sources & evidence

ORD record
ord-053bfaa978394d2dafa438a4eafdffa9
Source dataset
uspto-grants-1982_02
Patent number
US04316958

Reaction notes

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