A simple solution: When N,N‐dimethylformamide was used to direct the stereochemical course of glycosylation reactions, 1,2‐cis glycosylation products were formed with excellent selectivity. A straightforward highly α‐stereoselective glycosylation involving preactivation (see scheme) should find broad application and be especially useful for sequential glycosylation reactions to form oligosaccharides. LG=leaving group.
The proton gradient established by the pH difference across a biological membrane is essential for many physiological processes, including ATP synthesis and ion and metabolite transport. Currently, ionophores are used to study proton gradients, and determine their importance to biological functions of interest. Because of the lack of an easy method for monitoring the proton gradient across the inner envelope membrane of chloroplasts (ΔpHenv), whether the concentration of ionophores used can effectively abolish the ΔpHenv is not proven for most experiments. To overcome this hindrance, we tried to setup an easy method for real-time monitoring of the stromal pH in buffered, isolated chloroplasts by using fluorescent pH probes; using this method the ΔpHenv can be calculated by subtracting the buffer pH from the measured stromal pH. When three fluorescent dyes, BCECF-AM [2′,7′-bis-(2-carboxyethyl)-5-(and-6)-carboxyfluorescein acetoxymethyl ester], CFDA-SE [5(6)-Carboxyfluorescein diacetate succinimidyl ester] and SNARF-1 carboxylic acid acetate succinimidyl ester were incubated with isolated chloroplasts, BCECF-AM and CFDA-SE, but not the ester-formed SNARF-1 were taken up by chloroplasts and digested with esterase to release high levels of fluorescence. According to its relatively higher pKa value (6.98, near the physiological pH of the stroma), BCECF was chosen for further development. Due to shielding of the excitation and emission lights by chloroplast pigments, the ratiometric fluorescence of BCECF was highly dependent on the concentration of chloroplasts. By using a fixed concentration of chloroplasts, a highly correlated standard curve of pH to the BCECF ratiometric fluorescence with an r-square value of 0.98 was obtained, indicating the reliability of this method. Consistent with previous reports, the light-dependent formation of ΔpHenv can be detected ranging from 0.15 to 0.33 pH units upon illumination. The concentration of the ionophore nigericin required to collapse the ΔpHenv was then studied. The establishment of a non-destructive method of monitoring the stromal pH will be valuable for studying the roles of the ΔpHenv in chloroplast physiology.
Non-alcoholic fatty liver disease (NAFLD) is closely associated with metabolic disorders, including hepatic lipid accumulation and lipotoxicity. Plant-derived polyphenols have attracted considerable attention in the prevention of NAFLD. Lotus seedpod, rich in polyphenols, is a traditional Chinese herbal medicine. Previous studies have showed that lotus seedpod possess radioprotective, antioxidant, anti-cancer, and anti-inflammatory activities. In this study, the in vitro hepatoprotective effect of lotus seedpod extract (LSE) and its main component epigallocatechin (EGC) was examined. Firstly, oleic acid (OA), an unsaturated fatty acid, was used to induce the phenotype of NAFLD in human hepatocytes, HepG2 cells. LSE dose-dependently improved the OA-induced viability loss of HepG2 cells. Non-cytotoxic concentrations of LSE or EGC abolished intracellular lipid accumulation and oxidative stress in the OA-treated cells. In addition, LSE and EGC showed a minor effect on autophagy, and potential in reducing OA-induced occurrence of apoptosis confirmed by morphological and biochemical features, including an increase in the formation of apoptotic bodies, the exposure of phosphatidylserine, and activation of caspases. Molecular data showed the anti-apoptotic effect of LSE might be mediated via downregulation of the mitochondrial pathway. Our data imply that EGC-enriched LSE potentially could be developed as an anti-NAFLD agent.
Overexpression of glucose transporters (GLUTs) in colorectal cancer cells is associated with 5-fluorouracil (1, 5-FU) resistance and poor clinical outcomes. We designed and synthesized a novel GLUT-targeting drug conjugate, triggered by glutathione in the tumor microenvironment, that releases 5-FU and GLUTs inhibitor (phlorizin (2) and phloretin (3)). Using an orthotopic colorectal cancer mice model, we showed that the conjugate exhibited better antitumor efficacy than 5-FU, with much lower exposure of 5-FU during treatment and without significant side effects. Our study establishes a GLUT-targeting theranostic incorporating a disulfide linker between the targeting module and cytotoxic payload as a potential antitumor therapy.
Eine einfache Lösung: N,N‐Dimethylformamid führt bei Glycosylierungen mit ausgezeichneter stereochemischer Selektivität zu den 1,2‐cis‐Glycosylierungsprodukten. Eine unkomplizierte hoch α‐stereoselektive Glycosylierung über eine Präaktivierung (siehe Schema) sollte breit anwendbar und besonders nützlich für sequenzielle Glycosylierungen zum Aufbau von Oligosacchariden sein. LG=Abgangsgruppe.
Most natural 2‐acetamido‐2‐deoxyglycosides exist in a 1,2‐trans‐β‐glycosidic configuration. This study investigated the use of 2‐azido‐2‐deoxythioglycosides for 1,2‐trans‐β‐glycosidic bond formation under low‐concentration glycosylation conditions. Further application of the 2‐azido‐2‐deoxythioglycosyl substrates for one‐pot oligosaccharide synthesis was demonstrated in the synthesis of protected β‐(1→6)‐N‐acetylglucosamine trimer, core‐6–serine conjugate, and F1–α serine conjugate.
The total synthesis of a glycoglycerolipid isolate of Meiothermus taiwanensis and its truncated structural analogues is reported. Our synthesis employed DMF-modulated and low-concentration glycosylation reactions for the construction of α- and β-glycosidic bonds in the absence of participating protecting groups. Further simplification of the synthesis was achieved by employing a low-concentration one-pot glycosylation procedure. Preliminary immunological studies showed that one of the truncated structural analogues suppressed the cytokine production of THP-1 monocytes.
Flowering plants have evolved two distinct clades of chloroplast GrpE homologues (CGEs), which are the nucleotide exchange factor for Hsp70. In Arabidopsis, they are named AtCGE1 (At5g17710) and AtCGE2 (At1g36390). Characterization of their corresponding T-DNA insertion mutants revealed that there is no visible change in phenotype except a defect in protein import in an AtCGE2-knockout mutant under normal growth conditions. However, the embryo development of an AtCGE1-knockout mutant was arrested early at the globular stage. An AtCGE1-knockdown mutant, harboring a T-DNA insertion in the 5′-UTR region, exhibited growth retardation and protein import defect, and its mutant phenotypes became more severe when AtCGE2 was further knocked out. Sub-organellar distribution implied that AtCGE2 might be important for membrane biology due to its preferential association with chloroplast membranes. Biochemical studies and complementation tests showed that only AtCGE1, but not AtCGE2, can effectively rescue the heat-sensitive phenotype of Escherichia coli grpE mutant and robustly stimulate the refolding of denatured luciferase by DnaK. Interestingly, AtCGE1 and AtCGE2 are tending to form heterocomplexes, which exhibit comparable co-chaperone activity to AtCGE1 homocomplexes. Our data indicate that AtCGE1 is the principle functional homologue of GrpE. The possibility that AtCGE2 has a subsidiary or regulatory function through homo-and/or hetero-oligomerization is discussed.
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