Phosphate → Gentamicin C1

HRID 435513

Reaction equation

HRID 435513 reaction equation
CC(N)[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3OC[C@@](O)(C)[C@H](NC)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](N)CC1.[CH3:33][CH:34]([NH:64][CH3:65])[C@H:35]1[O:40][C@H:39]([O:41][C@H:42]2[C@H:47]([OH:48])[C@@H:46]([O:49][C@H:50]3[O:55][CH2:54][C@@:53]([OH:57])([CH3:56])[C@H:52]([NH:58][CH3:59])[C@H:51]3[OH:60])[C@H:45]([NH2:61])[CH2:44][C@@H:43]2[NH2:62])[C@H:38]([NH2:63])[CH2:37][CH2:36]1.C[C@@]1(O)[C@H](NC)[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC1.OS(O)(=O)=O.[OH-].[Ba+2].[OH-].[OH-].[K+].S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].P([O-])([O-])([O-])=O.[Na+].[Cl-]>O>[CH3:33][C@@H:34]([NH:64][CH3:65])[C@H:35]1[O:40][C@H:39]([O:41][C@H:42]2[C@H:47]([OH:48])[C@@H:46]([O:49][C@H:50]3[O:55][CH2:54][C@@:53]([OH:57])([CH3:56])[C@H:52]([NH:58][CH3:59])[C@H:51]3[OH:60])[C@H:45]([NH2:61])[CH2:44][C@@H:43]2[NH2:62])[C@H:38]([NH2:63])[CH2:37][CH2:36]1

Participants

8

Reactant 6

HCID 1061PhosphateHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 3423265Sodium Lauryl Sulfate2×HCID 6093286Barium hydroxideHCID 9855350Gentamicin Sulfate

Product 1

HCID 72395Gentamicin C1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

50 mg of gentamicin sulfate in 5 mL of water is neutralized by adding barium hydroxide until no further precipitate is formed. The precipitate, barium sulfate, is removed by centrifugation. The supernatant is added to a mixture of 5 mL of the polystyrene/polyglycidyl methacrylate polymer particle prepared in Example 4 and 5 mL of a 0.1% suspension of "Schercozoline" S (a substituted imidazoline from stearic acid, available from Scher Chemical Co.) at a pH of 8.5 adjusted with potassium hydroxide. The mixture is warmed to 75° C. for approximately 30 min, diluted with 200 mL of water, and deionized using a mixed bed ion exchange resin. 0.4 mL of the resulting particle reagent is added to 20 mL of 0.1% sodium dodecyl sulfate (SDS) followed by the addition of 0.2 mL of 0.020 M phosphate buffer (pH 7.43) containing 0.3 m NaCl and 0.1% SDS.

Workup

  1. customis formed
  2. customThe precipitate, barium sulfate, is removed by centrifugation
  3. additionThe supernatant is added to a mixture of 5 mL of the polystyrene/polyglycidyl methacrylate polymer particle
  4. customprepared in Example 4 and 5 mL of a 0.1% suspension of "Schercozoline" S (a substituted imidazoline from stearic acid

Sources & evidence

ORD record
ord-4cc75235e28f441db68ef87f907cfce9
Source dataset
uspto-grants-1983_08
Patent number
US04401765

Linked notes

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