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Article

OcUGT1-Catalyzing Glycodiversification of Steroids through Glucosylation and Transglucosylation Actions

Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College (State Key Laboratory of Bioactive Substance and Function of Natural Medicines & NHC Key Laboratory of Biosynthesis of Natural Products), Beijing 100050, China
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Author to whom correspondence should be addressed.
Academic Editor: Yasunori Yaoita
Molecules 2020, 25(3), 475; https://doi.org/10.3390/molecules25030475
Received: 8 January 2020 / Revised: 20 January 2020 / Accepted: 21 January 2020 / Published: 22 January 2020
(This article belongs to the Special Issue Natural Sterols)
Steroidal glycosides are important sources of innovative drugs. The increased diversification of steroidal glycosides will expand the probability of discovering active molecules. It is an efficient approach to diversify steroidal glycosides by using steroidal glycosyltransferases. OcUGT1, a uridine diphosphate-d-glucose (UDP-Glc)-dependent glycosyltransferase from Ornithogalum caudatum, is a multifunctional enzyme, and its glycodiversification potential towards steroids has never been fully explored. Herein, the glycodiversification capability of OcUGT1 towards 25 steroids through glucosylation and transglucosylation reactions were explored. Firstly, each of 25 compounds was glucosylated with UDP-Glc. Under the action of OcUGT1, five steroids (testosterone, deoxycorticosterone, hydrocortisone, estradiol, and 4-androstenediol) were glucosylated to form corresponding mono-glucosides and biosides. Next, OcUGT1-mediated transglucosylation activity of these compounds with another sugar donor ortho-nitrophenyl-β-d-glucopyranoside (oNPGlc) was investigated. Results revealed that the same five steroids could be glucosylated to generate mono-glucosides and biosides by OcUGT1 through transglucosylation reactions. These data indicated that OcUGT1-assisted glycodiversification of steroids could be achieved through glucosylation and transglucosylation reactions. These results provide a way to diversify steroidal glycosides, which lays the foundation for the increase of the probability of obtaining active lead compounds. View Full-Text
Keywords: glycodiversification; glucosylation; transglucosylation; glycosyltransferase; steroidal glycosides glycodiversification; glucosylation; transglucosylation; glycosyltransferase; steroidal glycosides
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MDPI and ACS Style

Xu, Y.-L.; Kong, J.-Q. OcUGT1-Catalyzing Glycodiversification of Steroids through Glucosylation and Transglucosylation Actions. Molecules 2020, 25, 475. https://doi.org/10.3390/molecules25030475

AMA Style

Xu Y-L, Kong J-Q. OcUGT1-Catalyzing Glycodiversification of Steroids through Glucosylation and Transglucosylation Actions. Molecules. 2020; 25(3):475. https://doi.org/10.3390/molecules25030475

Chicago/Turabian Style

Xu, Yan-Li; Kong, Jian-Qiang. 2020. "OcUGT1-Catalyzing Glycodiversification of Steroids through Glucosylation and Transglucosylation Actions" Molecules 25, no. 3: 475. https://doi.org/10.3390/molecules25030475

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