Synthesis of Camptothecin-10-O-glucoside Using an Engineered Oleandomycin Glucosyltransferase

Zhu, Xue-Lin; Qinmei, YE; Wen, Chao; Li-ping, Chen; Guangping, Liang; Zeng, Ting; Zhang, Dongmei; Jiang, Ren‐Wang

doi:10.1007/s40242-018-7309-9

Cited by 1 publication

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“…Glycosylation modification can enhance the water solubility, [7] targeting [8] and reduce the toxic and side effects of drugs [9] . Both chemical method [10] and enzymatic method [11] can achieve glycosylation, but enzymatic glycosylation has the advantages of green and high efficiency, [12] and thus its application is increasingly widespread. This article intends to modify bufalin via the chemo‐enzymatic strategy.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

Liu

Xü

Huang

et al. 2020

Chemistry & Biodiversity

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In this study, bufalin was glycosylated by an efficient chemo-enzymatic strategy. Firstly, 2-chloro-4nitrophenyl-1-O-β-D-glucoside (sugar donors) was obtained by chemical synthesis. Then, the glycosylation of the bufalin was achieved with the synthesized sugar donor under the catalysis of two glycosyltransferases (Loki and ASP). Finally, two glycosides, i. e., bufalin-3-O-β-D-glucopyranoside and bufalin-3-O-[β-D-glucopyranosyl-(1!2)-β-D-glucopyranoside)], were obtained by preparative HPLC. Compared to our previously reported sole chemical (total yield 10 % in four steps) or enzymatic methods (30 %), our combined chemo-enzymatic strategy in this article greatly improves the yields of monoglycoside (68 %) and diglycoside (21 %) and decreased the experimental cost (90 %). Furthermore, we tested the water solubility of these glycosides and found that the water solubilities of the two glycosides were 13.1 and 53.7 times of bufalin, respectively. In addition, the inhibitory activity of these glycosides against Na + , K +-ATPase were evaluated. The mono-glycosylated compound showed more potent activity than bufalin, while the diglycosylated compound was less potent.

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Section: Introductionmentioning

confidence: 99%

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

Liu

Xü

Huang

et al. 2020

Chemistry & Biodiversity

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show abstract

Synthesis of Camptothecin-10-O-glucoside Using an Engineered Oleandomycin Glucosyltransferase

Cited by 1 publication

References 16 publications

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

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Synthesis of Camptothecin-10-O-glucoside Using an Engineered Oleandomycin Glucosyltransferase

Cited by 1 publication

References 16 publications

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na+, K+‐ATPase

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na+, K+‐ATPase

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An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase

An Efficient Strategy for the Chemo‐Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na⁺, K⁺‐ATPase