94632-41-4Relevant articles and documents
Probing the catalytic promiscuity of a regio- and stereospecific C-glycosyltransferase from Mangifera indica
Chen, Dawei,Chen, Ridao,Wang, Ruishan,Li, Jianhua,Xie, Kebo,Bian, Chuancai,Sun, Lili,Zhang, Xiaolin,Liu, Jimei,Yang, Lin,Ye, Fei,Yu, Xiaoming,Dai, Jungui
supporting information, p. 12678 - 12682 (2015/10/28)
The catalytic promiscuity of the novel benzophenone C-glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio- and stereospecific C-glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP-glucose, and also formed O- and N-glycosides. Moreover, MiCGT was able to generate C-xylosides with UDP-xylose. The OGT-reversibility of MiCGT was also exploited to generate C-glucosides with simple sugar donor. Three aryl-C-glycosides exhibited potent SGLT2 inhibitory activities with IC50 values of 2.6×, 7.6×, and 7.6×10-7-M, respectively. These findings demonstrate for the first time the significant potential of an enzymatic approach to diversification through C-glycosidation of bioactive natural and unnatural products in drug discovery. C-glycodiversification: MiCGT, as the first benzophenone C-glycosyltransferase (CGT) from Mangifera indica, showed robust regio- and stereospecific C-glycosylation activity for 35 structurally diverse acceptors with UDP-glucose or xylose. The aryl-C-glycoside 1 exhibited potent antidiabetic activity toward SGLT2.
Enol Ethers, XIV. Acylation of Keto Enol Ethers with Malonyl Dichloride - A New Synthesis of Phloroglucinols
Effenberger, Franz,Schoenwaelder, Karl-Heinz
, p. 3270 - 3279 (2007/10/02)
Phloroglucinols 4 and/or 4-hydroxy-2H-pyran-2-ones 5 are formed from keto enol ethers 1 and malonyl dichloride (2a) in high yields.Since the pyranones 5 can be smoothly converted into phloroglucinols, the reaction of 1 with 2a represents a new, facile synthetic route to phloroglucinols.The reaction proceeds via formation of a chloro carbonyl ketene 8 and its subsequent reaction with 1.The product ratio 4:5 is rationalized in terms of substituent effects in the enol ether substrate.
