94632-41-4Relevant academic research and scientific papers
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.
DEOXYGENATION OF ALDEHYDES AND KETONES WITH SODIUM CYANOBOROHYDRIDE
Elliger, Carl A.
, p. 1315 - 1324 (2007/10/02)
Treatment of hydroxy-substituted aromatic aldehydes and ketones with sodium cyanoborohydride yields the corresponding methylene compounds under conditions which favor intermediate carbonium ion formation.
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.
CONDENSED TANNINS: COMPETING NUCLEOPHILIC CENTRES IN BIOMIMETIC CONDENSATION REACTIONS
Botha, Jacobus J.,Viviers, Phillip M.,Ferreira, Daneel,Roux, David G.
, p. 1289 - 1294 (2007/10/02)
The relative contributions of nucleophilicity and steric hindrance in determining the course of the reacition during the formation of 'angular' triflavonoids are examined by biomimetic-type condensations involving model compounds.Key Word Index - (4,6)-(-)-fisetinidol-8-(4-hydroxybenzyl)-(+)-catechins; 4-(3-ethyl-2,4,6-trihydroxyphenyl)-3,3',4',7-tetrahydroxyflavans; (4,3:4,5)-bi--ethyl phloroglucinols; condensed tannins; nucleophilicity; steric hindrance.
