10.1016/j.carres.2010.07.029
The research primarily focuses on the synthesis and widespread occurrence of monoterpenoid esters, cuniloside B and cypellocarpin C, in the Eucalyptus genus. Experiments involved the synthesis of these esters along with related natural products using reactants such as D-glucopyranose, (+)-(R)-oleuropeic acid, noreugenin, and various glycosides. The synthesis processes were optimized using different conditions and reagents, including phase transfer glycosylation, deacetylation with sodium methoxide, and acylation using HBTU–NMM–DMAP. The experiments also encompassed the extraction and analysis of leaf samples from 28 diverse eucalypt species, utilizing techniques like LC-ESIMS, NMR, and IR spectroscopy for compound identification and quantification. The study revealed that cuniloside B is present in all examined species, while cypellocarpin C is found in most, suggesting their potential roles in essential oil biosynthesis or mobilization.
10.1002/adsc.200404053
The research focuses on the synthesis of novel chiral aryl diphosphite ligands derived from the pyranoside backbones of glucose and galactose. These ligands were applied in copper-catalyzed asymmetric conjugate addition reactions of diethylzinc to cyclic enones, aiming to form new carbon-carbon bonds and chiral compounds with high enantioselectivity. The study investigated the impact of the ligand's stereochemistry on the reaction's enantioselectivity, revealing that it was influenced by the ligand's backbone stereocenters and the binaphthyl phosphite moieties' configuration. The experiments utilized various reactants, including different cyclic enones, Cu(OTf)2 as the copper source, and the newly synthesized ligands. Analyses of the products were conducted using techniques such as gas chromatography-mass spectrometry (GC-MS) and gas chromatography with a Chiraldex A-TA column to determine conversion, yield, and enantiomeric excess. The research also explored the effects of solvent and reaction temperature on enantioselectivity, finding that ethereal solvents and lower temperatures generally yielded better results.
10.1002/cbic.201000759
The research presents an in-depth study on the transport of free and peptide-bound glycated amino acids, focusing on their synthesis, transepithelial flux across Caco-2 cell monolayers, and interactions with apical membrane transport proteins. The experiments involved the synthesis of various glycated amino acids and dipeptides through non-enzymatic chemical processes known as the Maillard reaction, using reactants like lysine, arginine, glucose, and other sugars. The synthesized products were analyzed using techniques such as high-pressure liquid chromatography (HPLC), amino acid analysis (AAA), nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and elemental analysis. The study also measured the inhibition of lysine and glycylsarcosine uptakes in Caco-2 cells, which express transporters like PEPT1 and lysine transport systems, to understand the affinities and transport characteristics of these glycated compounds. The results provided insights into the intestinal absorption mechanisms of dietary Maillard reaction products and their potential impact on human health.
10.1016/j.ejmech.2017.03.088
The research presents a comprehensive study on the synthesis and in vitro antitumor activity of crassalactone D, its stereoisomers, and novel cinnamic ester derivatives. The purpose of the study was to develop a new one-pot synthesis method for these compounds starting from D-glucose and evaluate their cytotoxic effects against various human tumor cell lines. The conclusions drawn from the research indicate that many of the synthesized compounds exhibited potent cytotoxicities, with some showing higher potency than the commercial antitumor agent doxorubicin. The study also highlighted the importance of stereochemistry at the C-4 and C-7 positions, as well as the nature of the substituent at the C-4 position in the aromatic ring of the cinnamoate moiety, for biological activity. The chemicals used in the process included D-glucose, (methoxycarbonylmethylene)triphenylphosphorane (MCMP), (ethoxycarbonylmethylene)triphenylphosphorane (ECMP), cinnamoyl chloride, 4-nitrocinnamoyl chloride, 4-methoxycinnamic acid, and 4-fluorocinnamic acid, among others. The synthesized products were assessed for their in vitro antiproliferative activity, and the results were supported by flow cytometry and Western blot analysis, providing insights into the apoptotic mechanisms triggered by the compounds.
10.1021/jo0491051
The research focuses on the design and efficient synthesis of 2R-(ω-hydroxyalkoxy)-1R,25-dihydroxyvitamin D3 analogues, including 2-epi-ED-71 and their 20-epimers, with the aim of evaluating their activity in inducing HL-60 cell differentiation. The purpose of this study is to develop novel vitamin D3 analogues with high affinity for the vitamin D receptor (VDR) and potent biological activities, which could potentially lead to new drugs for the treatment of conditions such as rickets, osteoporosis, psoriasis, and certain cancers. The researchers utilized D-glucose as a chiral template to construct the 2R-modified A-ring precursors and employed a convergent synthetic approach, particularly Trost’s A-ring/CD-ring connective strategy, to synthesize the target molecules. Key chemicals used in the synthesis process include D-glucose, various alkanediols, KOtBu, TBSCl, NBS, Zn powder, NaBH3CN, LiHMDS, BF3·OEt2, and TMSCCH, among others. The study concluded that the VDR binding affinities of the synthesized 2R-(ω-hydroxyalkoxy)-1R,25(OH)2D3 compounds (4a, 4b, 20-epi-4a, and 20-epi-4b) were stronger than that of the natural hormone, and their 20-epi counterparts (20-epi-4a-c) showed higher potency in inducing HL-60 cell differentiation. These findings contribute to the understanding of the structure-activity relationships of vitamin D3 analogues and suggest that double modification on the 2R position and the side chain could be a promising approach for the development of new therapeutic agents.
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