Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase

Abstract The stereoselective xylosylation of ( RS )-1-phenylalkyl β- d -glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of ( RS )-1-phenylethyl β- d -glucoside afforded ( R )-1-phenylethyl β-primeveroside and ( S )-1-phenylethyl β- d -glucoside. The ( R )-selective xylosylation of ( RS )-1-phenylbutyl β- d -glucoside also occurred to give ( R )-1-phenylbutyl β-primeveroside and recovered ( S )-1-phenylbutyl β- d -glucoside.