88885-07-8Relevant 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
, p. 12678 - 12682 (2015)
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.
Scandium cation-exchanged montmorillonite catalyzed direct C-glycosylation of a 1,3-diketone, dimedone, with unprotected sugars in aqueous solution
Sato, Shingo,Naito, Yuzo,Aoki, Kazuyori
, p. 913 - 918 (2007)
The condensation of dimedone with unprotected sugars in aqueous solution in the presence of a catalytic amount of Sc3+-montmorillonite (Sc3+-mont) gave 9-hydroxyalkyl-3,3,6,6,-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dio
Synthesis and evaluation of a new water-soluble fluorescent red dye, xanthene bis-C-glycoside
Sato, Shingo,Nojiri, Toshikatsu,Okuyama, Nao,Maeda, Koya,Kirigane, Aoi
, p. 3342 - 3349 (2020)
Condensation of 2 eq. of C-β-D-glucosylphloroacetophenone with glyoxylic acid in an aqueous solution of Na2CO3, followed by air oxidation in MeOH in the presence of 11 eq. of pyridine to afford a 36percent yield of a bright red dye, xanthene bis-C-glycoside. This dye is 10 times more fluorescent (Φf [EtOH]581 nm = 3.9 × 10?2) and 7.5 times more water-soluble (57 mg/mL H2O) than the natural red pigment, carthamin. Detailed NMR analysis of its methyl analogs was used to confirm the structure of the dye as methyl 4,5-diacetyl-1,3,8-trihydroxy-3-oxo-3H-2,7-di-C-β-D-glucopyranosylxanthene-9-carboxylate from among three possible ring-closure isomers. Xanthene is safe and shows high light-resistance; therefore, xanthene bis-C-glycoside could be used as a food colorant or an in vivo probe.
Functional Characterization and Structural Basis of an Efficient Di-C-glycosyltransferase from Glycyrrhiza glabra
Chi, Chang-Biao,He, Jun-Bin,Li, Fu-Dong,Li, Kai,Liu, Zhen-Ming,Ma, Ming,Qiao, Xue,Shi, Xiao-Meng,Su, Hui-Fei,Wang, Yu-Xi,Wang, Zi-Long,Yang, Dong-Hui,Ye, Min,Yun, Cai-Hong,Zhang, Liang-Ren,Zhang, Meng,Zhang, Zhi-Yong,Zhang, Zhong-Yi
supporting information, p. 3506 - 3512 (2020/03/06)
A highly efficient di-C-glycosyltransferase GgCGT was discovered from the medicinal plant Glycyrrhiza glabra. GgCGT catalyzes a two-step di-C-glycosylation of flopropione-containing substrates with conversion rates of >98%. To elucidate the catalytic mech
