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

HRID 2163607Notes

Reaction equation

HRID 2163607 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH2:13]1[C@H:18]([NH2:19])[C@@H:17]([O:20][C@H:21]2[O:26][C@H:25]([CH2:27][NH2:28])[C@@H:24]([OH:29])[C@H:23]([OH:30])[C@H:22]2[OH:31])[C@H:16]([OH:32])[C@@H:15]([O:33][C@H:34]2[O:39][C@H:38]([CH2:40][OH:41])[C@@H:37]([OH:42])[C@H:36]([NH2:43])[C@H:35]2[OH:44])[C@@H:14]1[NH2:45].OS(O)(=O)=O>O>[CH2:13]1[C@H:18]([NH2:19])[C@@H:17]([O:20][C@H:21]2[O:26][C@H:25]([CH2:27][NH2:28])[C@@H:24]([OH:29])[C@H:23]([OH:30])[C@H:22]2[OH:31])[C@H:16]([OH:32])[C@@H:15]([O:33][C@H:34]2[O:39][C@H:38]([CH2:40][OH:41])[C@@H:37]([OH:42])[C@H:36]([NH2:43])[C@H:35]2[OH:44])[C@@H:14]1[NH2:45]

Participants

4

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 441374Kanamycin A Sulfate

Product 1

HCID 6032Kanamycin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A simulated kanamycin culture broth is prepared by sterilizing 160 ml glucose-bouillon medium under heating at 120° C for 15 minutes and adding kanamycin sulfate with 60 mg activity thereto. Then, the solution is passed through a column, 2 cm in diameter, wherein 6 g (dry weight) selective adsorbents containing activated charcoal as obtained in Example 1, after being sufficiently swelled with water, are packed, at the rate of 0.5 ml/minute. The column is then washed and further eluted with 0.1N HCl-methanol (1 : 1). Active fractions are combined, wherefrom kanamycin with 54 mg activity (90% recovery) is obtained in high purity and high yield (decoloration degree: 99%; purity: 98%).

Workup

  1. customThen, the solution is passed through a column, 2 cm in diameter, wherein 6 g (dry weight) selective adsorbents
  2. additioncontaining activated charcoal
  3. customas obtained in Example 1
  4. washThe column is then washed
  5. washfurther eluted with 0.1N HCl-methanol (1 : 1)
  6. customis obtained in high purity
  7. customhigh yield (decoloration degree: 99%; purity: 98%)

Sources & evidence

ORD record
ord-b6e828ffaedc4fef86938238a032e45e
Source dataset
uspto-grants-1979_01
Patent number
US04135943

Reaction notes

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