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Application of Racemization Process to Dynamic Resolution of (RS)-Phenylephrine to (R)-Phenylephrine β-D-Glucoside by Nicotiana tabacum Glucosyltransferase

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Enzymatic glucosylation of racemic phenylephrine by glucosyltransferase from Nicotiana tabacum gave (R)-phenylephrine glucoside and recovered (S)-phenylephrine. [RuCl2(p-cymene)]2 complex associated with simple hemisalen ligands or zeolite were able to racemize (S)-phenylephrine.… Click to show full abstract

Enzymatic glucosylation of racemic phenylephrine by glucosyltransferase from Nicotiana tabacum gave (R)-phenylephrine glucoside and recovered (S)-phenylephrine. [RuCl2(p-cymene)]2 complex associated with simple hemisalen ligands or zeolite were able to racemize (S)-phenylephrine. The [RuCl2(p-cymene)]2/Ligand/TEMPO or zeolite racemization was associated with the enantioselective glycosylation of racemic phenylephrine with glucosyltransferase. The (R)-stereoselective glucosylation of (RS)-phenylephrine occurred to produce a high yield of (R)-phenylephrine glucoside in high yield.

Keywords: racemization; glucosyltransferase; nicotiana tabacum; phenylephrine; phenylephrine glucoside

Journal Title: Natural Product Communications
Year Published: 2018

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