HCID 165579, compound → Paromomycin

HRID 429014Notes

Reaction equation

HRID 429014 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][OH:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[NH2:19])[C@H:4]([O:20][C@@H:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([O:28][C@H:29]3[O:34][C@@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]3[NH2:39])[C@H:22]2[OH:40])[C@@H:3]([OH:41])[C@@H:2]1[NH2:42].[O-]S([O-])(=O)=O.CN(C1C=CC2C(C3C=CC(C([O-])=O)=CC=3C(O)=O)=C3C(OC=2C=1)=CC(=[N+](C)C)C=C3)C>C(=O)(O)[O-].[Na+].CN(C)C=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][OH:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[NH2:19])[C@H:4]([O:20][C@@H:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([O:28][C@H:29]3[O:34][C@@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]3[NH2:39])[C@H:22]2[OH:40])[C@@H:3]([OH:41])[C@@H:2]1[NH2:42]

Participants

5

Reactant 2

HCID 165579HCID 165579, compoundHCID 27626025-TAMRA

Product 1

HCID 165580Paromomycin

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Paramomycin TAMRA was synthesized by reacting 55 mg paramomycin sulphate in sodium bicarbonate (6 mL 0.067M in 30% dimethyl formamide (DMF) with 5 mg 5-carboxytetramethyl rhodamine (in 1 mL DMF) over 12 hours at room temp. The solution was diluted and purified by anion exchange chromatography, and reversed phase HPLC (Wang et al., 1997).

Workup

  1. customover 12 hours
  2. customat room temp
  3. additionThe solution was diluted
  4. custompurified by anion exchange chromatography

Sources & evidence

ORD record
ord-0619db7ecae64eb199805b39007943a6
Source dataset
uspto-grants-2001_11
Patent number
US06316194B1

Reaction notes

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