Trifluoroacetic acid → An inositol
Reaction equation
C[C@H]1O[C@H]([O:8][C@@H:9]2[C@@H:14]([OH:15])[C@@H:13]([OH:16])[C@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[OH:19])[C@@H](N)C[C@@H]1NC(C(O)=O)=N.FC(F)(F)C(O)=O>>[CH:9]1([OH:8])[CH:10]([OH:19])[CH:11]([OH:18])[CH:12]([OH:17])[CH:13]([OH:16])[CH:14]1[OH:15]Participants
Procedure
The need for investigational and commercial quantities of D-chiro-inositol has led to the development of several methods for the isolation (by extraction from plant tissues), partial synthesis or complete synthesis of that compound. Especially promising is hydrolysis of the aminoglycoside kasugamycin (produced by fermentation of Streptomyces kasugaspinus) as described in U.S. Pat. No. 5,091,596 issued to Kennington et al. According to that patent, kasugamycin is treated with trifluoroacetic acid for 3 hours at 100° C., after which the resulting D-chiro-inositol is isolated by resin and gel chromatography and purified by recrystallization from 90% ethanol. Alternatively, kasugamycin may be treated with hydrochloric acid for 8 hours at 90° C., followed by isolation of the D-chiro-inositol by resin chromatography and subsequent purification.
Workup
- extractionThe need for investigational and commercial quantities of D-chiro-inositol has led to the development of several methods for the isolation (by extraction from plant tissues), partial synthesis or complete synthesis of that compound
- customhydrolysis of the aminoglycoside kasugamycin (produced by fermentation of Streptomyces kasugaspinus)
Sources & evidence
- ORD record
- ord-5666a995ca3645e9a346a5c028fbde95
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05932774
Reaction notes
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