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

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.

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(R)-1-Phenylethyl β-primeverosideC19H28O10De 92%[α]D25=-7.6 (c 0.41, MeOH)Source of chirality: diastereoselective xylosylation with xylosyltransferase from Catharanthus roseusAbsolute configuration: (1R)

(R)-1-Phenylbutyl β-primeverosideC21H32O10De 99%[α]D25=-9.0 (c 0.35, MeOH)Source of chirality: diastereoselective xylosylation with xylosyltransferase from Catharanthus roseusAbsolute configuration: (1R)