Fluorescein 5-isothiocyanate → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 1845831Notes

Reaction equation

HRID 1845831 reaction equation
[CH:1]1[C:6](N=C=S)=[CH:5][C:4]2[C:10]([O:12][C:13]3([C:23]4[CH:24]=[CH:25][C:26]([OH:28])=[CH:27][C:22]=4[O:21][C:15]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]3=4)[C:3]=2[CH:2]=1)=[O:11]>C([O-])(O)=O.[Na+]>[CH:1]1[CH:6]=[CH:5][C:4]([C:10]([OH:12])=[O:11])=[C:3]([C:13]2[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[O:21][C:22]3[C:23]=2[CH:24]=[CH:25][C:26]([CH:27]=3)=[O:28])[CH:2]=1

Participants

3

Reactant 1

HCID 18730Fluorescein 5-isothiocyanate

Product 1

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

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A quantity of fluorescein isothiocyanate sufficient to modify one amine group in about every 2000 is added to a solution of chitlac (200 mg, Mw˜1.5×106 of ex. 1) in NaHCO3 0.5 M (65 mL). The solution is maintained under agitation in darkness for 24 hours, dialyzed against NaHCO3 0.05 M (3 changes) and against deionized water until conductivity is 4 μS at 4° C. Finally, the solution is filtered through 0.45 μm Millipore filters and lyophilized.

Workup

  1. temperatureThe solution is maintained under agitation in darkness for 24 hours
  2. customdialyzed against NaHCO3 0.05 M (3 changes) and against deionized water until conductivity
  3. customat 4° C
  4. filtrationFinally, the solution is filtered through 0.45 μm Millipore

Sources & evidence

ORD record
ord-fc885e38e8634bf89a7880188272b224
Source dataset
uspto-grants-2015_02
Patent number
US08951991B2

Reaction notes

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