NADP nicotinamide-adenine-dinucleotide phosphate → 1,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate

Participants

Reaction Conditions

Reaction Steps

Glucose dehydrogenase (manufactured by Amano Enzyme) 2000 U, glucose 2 g, NADP 6 mg, (3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 2.5 g were added to 50 ml of a cell-free extract of E. coli HB101 (pNTOM3) prepared in Example 7, and the mixture was stirred at 30° C. for 22 hr while adjusting to pH 6.5 by dropwise addition of 5 M sodium hydroxide. After completion of the reaction, the reaction mixture was extracted with toluene, desolvated and the extract was analyzed. As a result, (2R,3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanol (yield 86.3%, diastereomeric excess 96.4% d.e.) was obtained.

Provenance & Evidence