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Regulated preparation of Crocin-1 or Crocin-2' Triggered by the Cosolvent DMSO Using Bs-GT/At-SuSy One-Pot Reaction
Feng Liu, Fangyu Ding, Wenming Shao
1State Key Laboratory of Natural Medicines, Key Laboratory of Drug Metabolism and Pharmacokinetics , China Pharmaceutical University , Tongjiaxiang 24 , Nanjing 210009 , China.
Abstract:
Crocins are the primary coloring ingredients of saffron. The low-glycosylated members of this compound family, such as crocin-1 (crocetin mono-glucosyl ester) and crocin-2' (crocetin di-glucosyl ester), are rarely distributed in nature and attracting interest for their therapeutic uses. In the present study, a one-pot reaction system was used for efficient preparation of crocin-1 and crocin-2' with in situ regeneration of UDP-Glc by coupling Bs-GT with At-SuSy, a sucrose synthase from Arabidopsis thaliana. Noticeably, DMSO was used as a cosolvent and resulted in improvement of the solubility of the substrate crocetin and regulation of the selectivity of glycosylation. With periodic addition of crocetin, the biosynthesis of crocin-2' was performed with a high yield of 3.25 g/L in 2% DMSO aqueous solution, whereas crocin-1 (2.12 g/L) was selectively obtained in a 10% DMSO aqueous solution. The present study provided a simple approach for the biosynthesis of crocin-1 and crocin-2'.
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