Glutaraldehyde → Penicillin G

HRID 2118945Notes

Reaction equation

HRID 2118945 reaction equation
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([O-:22])=[O:21].[K+].C1(CC([O-])=O)C=CC=CC=1.[NH4+].C(=O)CCCC=O.[NH2:43][CH2:44][CH2:45][O:46][S:47](=[O:50])(=[O:49])[OH:48]>>[NH2:43][CH2:44][CH2:45][O:46][S:47](=[O:49])(=[O:48])[OH:50].[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 3485Glutaraldehyde3×HCID 70223Aminoethyl sulfate2×HCID 81607Benzeneacetic acid, ammonium saltHCID 23664709Penicillin G Potassium

Product 2

HCID 5904Penicillin GHCID 70223Aminoethyl sulfate

Procedure

Escherichia coli ATCC 9637 is used for the production of penicillin acylase. The nutrient solution consists of 2% of corn steep liquor plus 1% of ammonium phenylacetate, and the pH value is 6.5. 200 ml of nutrient solution are inoculated with 1 ml of an Escherichia coli suspension in a 1 liter conical flask. The fermentation proceeds at 31° C. for 20 hours on a rotary shaking machine at 290 rpm. 20 ml of 4% strength tannin solution are first added dropwise to 500 ml of cell suspension, and the suspension is then flocculated completely with the aid of 100 ml of BETZ/glutaraldehyde mixture (60 g/liter of BETZ, 2.2% v/v of glutaraldehyde, pH 9.0). When flocculation is complete, a 50% excess of BETZ/glutaraldehyde are immediately added. Half of the batch is immediately replaced with solid (I) to a final concentration of 0.1M, in addition to the excess of BETZ/glutaraldehyde, and the other half is worked up without (I). After the cell mass has been separated off, washed and extruded, it is dried overnight at 40° to 45° C. and then ground and sieved. Without (I), splitting of penicillin G in 6-aminopenicillanic acid and phenylacetic acid gave a specific activity of 2.17 pen G units per gram of dry catalyst, corresponding to 8.36 NIPAB units/g.

Workup

  1. customAfter the cell mass has been separated off
  2. washwashed
  3. customit is dried overnight at 40° to 45° C.
  4. filtrationground and sieved

Sources & evidence

ORD record
ord-19cad18e2cd841eb9d0e68bc33f54eee
Source dataset
uspto-grants-1987_07
Patent number
US04681843

Reaction notes

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