113960-55-7

Basic information

• Product Name: bufalin-3-(β-D-glucoside)
• Synonyms: bufalin-3-(β-D-glucoside)
• CAS NO: 113960-55-7
• Molecular Weight: 548.674
• Mol File: 113960-55-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: bufalin-3-(β-D-glucoside)(CAS DataBase Reference)
• NIST Chemistry Reference: bufalin-3-(β-D-glucoside)(113960-55-7)
• EPA Substance Registry System: bufalin-3-(β-D-glucoside)(113960-55-7)

Safety Data

• Hazardous Substances Data: 113960-55-7(Hazardous Substances Data)

Upstream product

• 120221-14-9 (2-chloro-4-nitrophenyl)-β-D-glucopyranoside 
• 465-20-3 bufalin 
• 133-89-1 diphosphoric acid 1''-β-D-[1'']glucopyranosyl ester 2-(uridin-5'-yl)ester 
• 133-89-1 UDP-glucose 
• 551-15-5 liquiritin 
• 486-62-4 ononin 

Relevant articles and documents

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

In this study, bufalin was glycosylated by an efficient chemo-enzymatic strategy. Firstly, 2-chloro-4-nitrophenyl-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.

An Efficient One-Pot Enzymatic Synthesis of Cardiac Glycosides with Varied Sugar Chain Lengths

An efficient one-pot enzymatic synthesis of cardiac glycosides with varied sugar chain lengths (average yield >80%) was carried out through sequential glycosylation using a steroid glycosyltransferase UGT74AN3 from Catharanthus roseus and a cyclodextrin glycosyltransferase from Bacillus licheniformis. A series of cardiac glycosides were obtained and showed enhanced affinity and selectivity for inhibition of the α2 isoform of Na+/K+-ATPase. These findings demonstrate the significant potential of the one-pot biocatalytic approach in the synthesis of diverse cardiac glycosides as potentially safer cardiotonic agents. (Figure presented.).

Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids?

The glycosyltransferase OleD variant as a catalyst for the glycosylation of four pairs of epimers of cardiotonic steroids (CTS) are assessed. The results of this study demonstrated that the OleD-catalyze glycosylation of CTS is significantly influenced by