40004-96-4Relevant academic research and scientific papers
Synthesis of cinnamoyl glucoside derivatives and their antiproliferation activities against murine melanoma B16-F10 cell line
Shu, Penghua,Yu, Mengzhu,Li, Yamin,Luo, Yuehui,Liu, Hao,Zhu, Huiqing,Zhang, Jialong,Zhang, Lingxiang,Wei, Xialan,Xiao, Fugang
, (2021)
Twelve cinnamoyl glucoside derivatives were prepared by glycosylation of glucosyl trichloroacetimidate and cinnamic acid derivatives, followed by dechloroacetylation with a pyridine/H2O mixture. Their structures were characterized by 1H and 13C NMR, as well as mass analysis. All the products were tested for their antiproliferation activities against murine melanoma B16-F10 cell line. Compounds 4e-4j were able to inhibit the proliferation of murine melanoma B16-F10 cell line with IC50 values of 17.38 ± 0.07, 9.87 ± 0.09, 9.69 ± 0.12, 29.42 ± 0.04, 32.95 ± 0.08, 25.68 ± 0.09 μM, respectively.
Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses
Fujimori, Yusuke,Furuta, Takumi,Kawabata, Takeo,Nagaishi, Masaru,Sasamori, Takahiro,Shibayama, Hiromitsu,Takeuchi, Hironori,Tokitoh, Norihiro,Ueda, Yoshihiro,Yoshimura, Tomoyuki
supporting information, (2020/06/29)
An SN2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected α-d-glucose under Mitsunobu conditions in dioxane, while an SN1 mechanism was indicated for nonstereoselective glycosylation in DMF. The SN2-type stereoselective Mitsunobu glycosylation is generally applicable to various unprotected pyranoses as glycosyl donors in combination with a wide range of acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One-or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented here using unprotected α-d-glucose.
Engineering faster transglycosidases and their acceptor specificity
Tran, Linh T.,Blay, Vincent,Luang, Sukanya,Eurtivong, Chatchakorn,Choknud, Sunaree,González-Diáz, Humbert,Ketudat Cairns, James R.
supporting information, p. 2823 - 2836 (2019/06/13)
Transglycosidases are enzymes that have the potential to catalyze the synthesis of a wide range of high-value compounds starting from biomass-derived feedstocks. Improving their activity and broadening the substrate range are important goals to enable the widespread application of this family of biocatalysts. In this work, we engineered 20 mutants of the rice transglycosidase Os9BGlu31 and evaluated their catalysis in 462 reactions over 18 different substrates. This allowed us to identify mutants that expanded their substrate range and showed high activity, including W243L and W243N. We also developed double mutants that show very high activity on certain substrates and exceptional specificity towards hydrolysis, such as L241D/W243N. In order to guide a more general use of Os9BGlu31 variants as transglycosylation catalysts, we built cheminformatics models based on topological descriptors of the substrates. These models showed useful predictive potential on the external validation set and are allowing the identification of efficient catalytic routes to novel phytohormone and antibiotic glucoconjugates of interest.
Carbohydrate esters of cinnamic acid from fruits of Physalis peruviana, Psidium guajava and Vaccinium vitis-idaea
Latza, Stefan,Gansser, Dietmar,Berger, Ralf G.
, p. 481 - 485 (2007/10/03)
1-O-trans-Cinnamoyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranose was isolated from fruits of Physalis peruviana and 1-O-trans-cinnamoyl-α-L- arabinofuranosyl-(1 → 6)-β-D-glucopyranose was obtained from fruits of Psidium guajava. Fruits of Vaccinium vitis-idaea and P. guajava were found to be rich sources of 1-O-trans-cinnamoyl-β-D-glucopyranose.
