Kanamycin A Sulfate → (2S,3R,4R,5S,6S)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol

HRID 505833

Reaction equation

HRID 505833 reaction equation
[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@H:9]2[O:14][C@H:13]([CH2:15][NH2:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[OH:19])[C@H:4]([OH:20])[C@@H:3]([O:21][C@H:22]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]([NH2:31])[C@H:23]2[OH:32])[C@@H:2]1[NH2:33].OS(O)(=O)=O>O>[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@@H:9]2[O:14][C@@H:13]([CH2:15][NH2:16])[C@H:12]([OH:17])[C@@H:11]([OH:18])[C@@H:10]2[OH:19])[C@H:4]([OH:20])[C@@H:3]([O:21][C@H:22]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]([NH2:31])[C@H:23]2[OH:32])[C@@H:2]1[NH2:33]

Participants

3

Reactant 1

HCID 441374Kanamycin A Sulfate

Product 1

HCID 11274101(2S,3R,4R,5S,6S)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triolYield 113.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Kanamycin sulfate (20.0 g) was dissolved in 200 mL of water. This was loaded on a column prepared with 400 g of AMBERLITE IRA-140 resin (6.4 cm×17.5 cm). The column was eluted with water, and the appropriate fractions were collected and lyophilized to give 18.9 g of kanamycin A (free base) (18).

Workup

  1. customprepared with 400 g of AMBERLITE IRA-140 resin (6.4 cm×17.5 cm)
  2. washThe column was eluted with water
  3. customthe appropriate fractions were collected

Sources & evidence

ORD record
ord-475ee180131f46c7bdd3e9346254273f
Source dataset
uspto-grants-2010_08
Patent number
US07781570B2

Linked notes

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