Microbiology and Biotechnology Letters (한국미생물·생명공학회지)

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
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Biosynthesis of Three Chalcone β-D-glucosides by Glycosyltransferase from Bacillus subtilis ATCC 6633

  • Fei, Yinuo (State Key Laboratory of Natural Medicines, China Pharmaceutical University) ;
  • Shao, Yan (State Key Laboratory of Natural Medicines, China Pharmaceutical University) ;
  • Wang, Weiwei (State Key Laboratory of Natural Medicines, China Pharmaceutical University) ;
  • Cheng, Yatian (State Key Laboratory of Natural Medicines, China Pharmaceutical University) ;
  • Yu, Boyang (State Key Laboratory of Natural Medicines, China Pharmaceutical University) ;
  • He, Xiaorong (School of Engineering, China Pharmaceutical University) ;
  • Zhang, Jian (State Key Laboratory of Natural Medicines, China Pharmaceutical University)
  • Received : 2021.02.25
  • Accepted : 2021.03.26
  • Published : 2021.06.28
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Abstract

Chalcones exhibit multiple biological activities. Various studies have attempted to modify the structure of chalcones with a special focus on the addition of substituents to the benzene rings. However, these chemical modifications did not improve the water solubility and bioavailability of chalcones. Glycosylation can markedly affect the physical and chemical properties of hydrophobic compounds. Here, we evaluated the ability of a highly promiscuous glycosyltransferase (GT) BsGT1 from Bacillus subtilis ATCC 6633 to biosynthesize chalcone glucosides. Purified BsGT1 catalyzed the conversion of 4'-hydroxychalcone (compound 1), 4'-hydroxy-4-methylchalcone (compound 2), and 4-hydroxy-4'-methoxychalcone (compound 3), into chalcone 4'-O-β-D-glucoside (compound 1a), 4-methylchalcone 4'-O-β-D-glucoside (compound 2a), and 4'-methoxychalcone 4-O-β-D-glucoside (compound 3a), respectively. To avoid the addition of expensive uridine diphosphate glucose (UDP-Glc), a whole-cell biotransformation system was employed to provide a natural intracellular environment for in situ co-factor regeneration. The yields of compounds 1a, 2a, and 3a were as high as 90.38%, 100% and 74.79%, respectively. The successful co-expression of BsGT1 with phosphoglucomutase (PGM) and UDP-Glc pyrophosphorylase (GalU), which are involved in the biosynthetic pathway of UDP-Glc, further improved the conversion rates of chalcones (the yields of compounds 1a and 3a increased by approximately 10%). In conclusion, we demonstrated an effective whole-cell biocatalytic system for the enzymatic biosynthesis of chalcone β-D-glucoside derivatives.

Keywords

Acknowledgement

This work was supported by National Nature Science Foundation of China (NSFC NO. 21302052) and the "Program for New Century Excellent Talents in University" awarded to Prof. Jian Zhang (NECT-11-0739). Thanks also give to Postgraduate Research & Practice Innovation Program of Jiangsu Province (SJKY19_0658).

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