Dimethyl Sulfoxide → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 1099118Notes

Reaction equation

HRID 1099118 reaction equation
C(=O)([O-])[O-].CS(C)=O.[CH:9]1[C:14](N=C=S)=[CH:13][C:12]2[C:18]([O:20][C:21]3([C:31]4[CH:32]=[CH:33][C:34]([OH:36])=[CH:35][C:30]=4[O:29][C:23]4[CH:24]=[C:25]([OH:28])[CH:26]=[CH:27][C:22]3=4)[C:11]=2[CH:10]=1)=[O:19]>O>[CH:9]1[CH:14]=[CH:13][C:12]([C:18]([OH:20])=[O:19])=[C:11]([C:21]2[C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=3[O:29][C:30]3[C:31]=2[CH:32]=[CH:33][C:34]([CH:35]=3)=[O:36])[CH:10]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 18730Fluorescein 5-isothiocyanateHCID 19660Carbonate Ion

Product 1

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The HA-HZ as obtained above (Example 10-1) was dissolved in distilled water (Milli Q water), resulting in a concentration of 20.0 mg/ml. Thereafter, a 0.25 M carbonate buffer (pH 9.0; 4.84 ml) and a DMSO solution (2.42 ml) that contained 101.3 mg/ml FITC were added to the above obtained solution, and the obtained mixture was gently shaken in the dark at room temperature for 1 hour. Thereafter, the resultant was dialyzed against an excessive amount of PBS for purification. The external dialysis solution was exchanged with distilled water (Milli Q water), followed by further dialysis and purification (Spectrapore 4; molecular weight cut off (MWCO): 12 k-14 kDa). The obtained aqueous solution was freeze-dried, so as to obtain fluorescein-labeled HA-HZ (227.63 mg).

Workup

  1. customThe HA-HZ as obtained above (Example 10-1)
  2. customresulting in a concentration of 20.0 mg/ml
  3. additionwere added to the above obtained solution
  4. customThereafter, the resultant was dialyzed against an excessive amount of PBS for purification
  5. customfollowed by further dialysis and purification (Spectrapore 4; molecular weight cut off (MWCO): 12 k-14 kDa)
  6. customThe obtained aqueous solution was freeze-dried

Sources & evidence

ORD record
ord-0459f72be5ce447fa98fa3264321e1b3
Source dataset
uspto-grants-2012_03
Patent number
US08143391B2

Reaction notes

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