Method for producing chiro-inositol

• US 5,091,596 A
• Filed: 12/20/1990
• Issued: 02/25/1992
• Est. Priority Date: 12/20/1990
• Status: Expired due to Fees

• Current Assignee: The University of Virginia Patent Foundation
• Original Assignee: University of Virginia Patent Foundation (University of Virginia)
• Inventors: Hill, Cynthia, Kennington, Allison, Stringfield, Butler, Kirwan, Donald J., Larner, Joseph, Carta, Giorgio
• Primary Examiner(s): LONE, WERREN
• Application Number:
  US07/631,374
• Time in Patent Office: 432 Days
• Field of Search: 568/833, 568/832
• US Class Current: 568/833
• CPC Class Codes: C07C 35/16 Inositols

Abstract

Kasugamycin has been recognized to be a source from which D-chiro-inositol can be easily obtained at low cost and high yield.

Claims

1. A method of producing D-chiro-inositol from kasugamycin, comprising the steps of:

providing a quantity of kasugamycin;

hydrolyzing said quantity of kasugamycin with a hydrolyzing agent under suitable time and temperature conditions so as to obtain an aqueous mixture of D-chiro-inositol and reaction products from said quantity of kasugamycin;

passing said aqueous mixture of D-chiro-inositol and reaction products through a cation exchange medium capable of binding anionic reaction products and impurities in said aqueous mixture and an anion exchange medium capable of binding cationic reaction products and impurities;

removing other impurities from an eluate from said cation and anion exchange medium; and

obtaining D-chiro-inositol from said eluate.

2. A method as recited in claim 1 wherein said step of obtaining D-chiro-inositol is performed by partial drying of said eluate and then freeze drying a remaining fraction.

3. A method as recited in claim 1 wherein said step of obtaining said D-chiro-inositol is performed by completely drying said eluate to obtain dried D-chiro inositol.

4. A method as recited in claim 3 further comprising the step of purifying said dried D-chiro-inositol.

5. A method as recited in claim 4 wherein said step of purifying includes recrystallization.

6. A method as recited in claim 1 wherein said step of hydrolyzing is performed with an acidic hydrolyzing reagent.

7. A method as recited in claim 6 wherein said temperature conditions range from 80°

C. to 100°

C.

8. A method as recited in claim 6 wherein said time conditions range from three to eight hours.

9. A method as recited in claim 1 wherein said step of removing other impurities is performed using activated carbon.

10. A method as recited in claim 1 wherein said step of removing other impurities is performed using C18 flash chromatography gel.