1-(Hydroxymethyl)-5-{[4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexane-1,2,3,4-tetrol → 5-Amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

Validoxylamine G (100 mg) was dissolved in 0.05 M phosphate buffer (pH 7.0) (20 mL) and wet cells of Flavobacterium saccharophilum IFO 13984 (about 2 g) were added to the solution, followed by incubation at 27° C. for 24 hours with stirring. The reaction mixture was centrifuged for removal of cells, and the supernatant was adsorbed onto a column (50 mL) of Amberlite IRC-50 (NH4+ form, manufactured by Rohm & Haas Co.), followed by washing with water and elution aqueous ammonia. The eluate was concentrated to dryness under reduced pressure, and the residue was adsorbed again onto a column (50 mL) of Amberlite IRC-50 (NH4+ form) and eluted with 0.1N aqueous ammonia. In succession to the fractions containing valienamine (eluate fractions 120-140 mL), the fractions containing valiolamine were eluted (eluate fractions 340-430 mL). The fractions containing valiolamine were concentrated to dryness under reduced pressure, and the residue was submitted to column chromatography on Dowex 1× 2 (OH- form, manufactured by Dow Chemicals Co.; 2 mL) followed by concentration of the eluate to dryness under reduced pressure, to give white powders of valiolamine (35 mg).

1. customThe reaction mixture was centrifuged for removal of cells
2. washby washing with water and elution aqueous ammonia
3. concentrationThe eluate was concentrated to dryness under reduced pressure
4. washeluted with 0.1N aqueous ammonia
5. additionIn succession to the fractions containing valienamine (eluate fractions 120-140 mL)
6. additionthe fractions containing valiolamine
7. washwere eluted (eluate fractions 340-430 mL)
8. additionThe fractions containing valiolamine
9. concentrationwere concentrated to dryness under reduced pressure

ORD record

ord-656274de70d8434392ffeac0d5842c1b

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04923975