Water → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Participants

Reaction Steps

A 300 g amount of nojirimycin was dissolved in 1.5 l of distilled water to which was added 80 g of deoxin-1, i.e., a crude powder of glucose oxidase with 10,000 units per mg which is produced by Penicillium amagasakiensis (produced by Nagase Sangyo Co./Japan). The pH of the reaction mixture was adjusted to 6.0 and then the reaction was conducted at 30°C in a 30 l jar fermenter with agitation at 300 r.p.m. under air-flowing conditions. After 65 hours of reaction, the reaction solution was passed through a column filled with Amberlite IR-120 (H+ type, 1.5 l). The column was then washed with 7 l of water. The treated solution and the washings were combined (22 l), and the combined solution was then neutralized with Amberlite IR-45 (OH- type), followed by decolorization with 50 g of carbon powder. The decolorized solution was then condensed. To the condensed solution (500 ml) was added 100 ml of methanol, which was allowed to stand to cool in order to yield a crystalline product. The crystals were separated from the solution by filtration to give 220 g of D-gluconic-δ-lactam as needle-like white crystals (yield of 77%).

Provenance & Evidence