Mineralization of “non-metabolizable” glucose analogues in soil: potential chemosensory mimics of glucose

2017 ◽  
Vol 180 (2) ◽  
pp. 165-168
Author(s):  
Kyle Mason-Jones ◽  
Aliia Gilmullina ◽  
Yakov Kuzyakov
Keyword(s):  
Glucose Analogues

A Fast and Sensitive Method Combining Reversed-Phase Chromatography with High Resolution Mass Spectrometry to Quantify 2-Fluoro-2-Deoxyglucose and Its Phosphorylated Metabolite for Determining Glucose Uptake

2019 ◽  
Author(s):  
Ashley Williams ◽  
Deborah Muoio ◽  
Guofang Zhang
Keyword(s):  
Glucose Uptake ◽  
Biological Samples ◽  
High Resolution Mass Spectrometry ◽  
Reversed Phase ◽  
Sodium Adduct ◽  
Negative Mode ◽  
Glucose Analogues ◽  
Positive Mode ◽  
Q Exactive ◽  
Glucose Analogue

Quantative measurements of the glucose analogue, 2-deoxyglucose (2DG), and its phosphorylated metabolite (2-deoxyglucose-6-phosphate (2DG-6-P)) are critical for the measurement of glucose uptake. While the field has long identified the need for sensitive and reliable assays that deploy non-radiolabled glucose analogues to assess glucose uptake, no analytical MS-based methods exist to detect trace amounts in complex biological samples. In the present work, we show that 2DG is poorly suited for MS-based methods due to interfering metabolites. We therefore developed and validated an alternative C18-based LC-Q-Exactive-Orbitrap-MS method using 2-fluoro-2-deoxyglucose (2FDG) to quantify both 2FDG and 2FDG-6-P by measuring the sodium adduct of 2FDG in the positive mode and deprotonation of 2FDG-6-P in the negative mode. The low detection limit of this method can reach 81.4 and 48.8 fmol for both 2FDG and 2FDG-6-P, respectively. The newly developed method was fully validated via calibration curves in the presence and absence of biological matrix. The present work is the first successful LC-MS method that can quantify trace amounts of a nonradiolabeled glucose analogue and its phosphorylated metabolite and is a promising analytical method to determine glucose uptake in biological samples.

Inhibition of germination by glucose analogues that are hexokinase substrates

1998 ◽  
Vol 48 (2) ◽  
pp. 241-248 ◽  
Author(s):  
Norman K. Matheson ◽  
David K. Myers
Keyword(s):  
Glucose Analogues

Antiviral activity of uridine 5′-diphosphate glucose analogues against some enveloped viruses in cell culture

1987 ◽  
Vol 8 (5-6) ◽  
pp. 299-310 ◽  
Author(s):  
G. Gil-Fernández ◽  
S. Pérez ◽  
P. Vilas ◽  
C. Pérez ◽  
F.G. de las Heras ◽  
...  
Keyword(s):  
Cell Culture ◽  
Antiviral Activity ◽  
Enveloped Viruses ◽  
Glucose Analogues ◽  
Diphosphate Glucose

Glycolytic component of rat spermatid energy and acid-base metabolism

1990 ◽  
Vol 259 (4) ◽  
pp. C660-C667 ◽  
Author(s):  
J. G. Reyes ◽  
M. V. Velarde ◽  
R. Ugarte ◽  
D. J. Benos
Keyword(s):  
Lactate Production ◽  
Co2 Production ◽  
Simultaneous Occurrence ◽  
Atp Content ◽  
Extracellular Medium ◽  
Glucose Addition ◽  
Intracellular Atp ◽  
Acid Diffusion ◽  
Glucose Analogues ◽  
The Impact

The impact of glycolysis on rat spermatid energy metabolism is made apparent by the simultaneous occurrence of the following three events upon glucose addition to the extracellular medium of a rat spermatid cell suspension: decrease in ATP content, exit of acid equivalents, and increased lactate production and efflux. In this work, we have studied the interrelations between these three phenomena. By measuring ATP content, net acid transport, lactate exit, oxygen consumption, intracellular pH, CO2 production, and glycolytic intermediates in the presence of glucose and glucose analogues, we conclude that 1) lactate production, decrease in ATP content, and acid equivalent exit are dependent on the metabolism of glucose up to different stages in glycolysis. 2) The decrease in ATP content is not directly related to the exit of acid equivalents from rat spermatids. 3) Glucose metabolism is a net ATP-consuming process at high intracellular ATP content but is a net ATP-producing process at low intracellular ATP concentration in rat spermatids. 4) Acid equivalent production arises from the metabolism of glucose beyond glyceraldehyde 3-phosphate dehydrogenase. 5) Lactic acid diffusion and/or lactate transport and CO2 production and exit could account for the glucose-dependent acid equivalent efflux in rat spermatids.

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

2020 ◽  
Vol 26 (59) ◽  
pp. 13499-13506 ◽  
Author(s):  
Jacob St‐Gelais ◽  
Émilie Côté ◽  
Danny Lainé ◽  
Paul A. Johnson ◽  
Denis Giguère
Keyword(s):  
Structural Complexity ◽  
Solvation Effects ◽  
Glucose Analogues ◽  
Insight Into

scholarly journals Analysis of the structural requirements of sugar binding to the liver, brain and insulin-responsive glucose transporters expressed in oocytes

1993 ◽  
Vol 294 (3) ◽  
pp. 753-760 ◽  
Author(s):  
C A Colville ◽  
M J Seatter ◽  
G W Gould
Keyword(s):  
Hydrogen Bond ◽  
Binding Sites ◽  
Glucose Transporters ◽  
Binding Pocket ◽  
Structural Basis ◽  
Sugar Binding ◽  
Glucose Analogues ◽  
Sugar Recognition

We have expressed the liver (GLUT 2), brain (GLUT 3) and insulin-responsive (GLUT 4) glucose transporters in oocytes from Xenopus laevis by microinjection of in vitro-transcribed mRNA. Using a range of halogeno- and deoxy-glucose analogues, and other hexoses, we have studied the structural basis of sugar binding to these different isoforms. We show that a hydrogen bond to the C-3 position is involved in sugar binding for all three isoforms, but that the direction of this hydrogen bond is different in GLUT 2 from either GLUT 1, 3 or 4. Hydrogen-bonding at the C-4 position is also involved in sugar recognition by all three isoforms, but we propose that in GLUT 3 this hydrogen bond plays a less significant role than in GLUT 2 and 4. In all transporters we propose that the C-4 position is directed out of the sugar-binding pocket. The role of the C-6 position is also discussed. In addition, we have analysed the ability of fructopyranose and fructofuranose analogues to inhibit the transport mediated by GLUT2. We show that fructofuranose analogues, but not fructopyranose analogues, are efficient inhibitors of transport mediated by GLUT 2, and therefore suggest that GLUT 2 accommodates D-glucose as a pyranose ring, but D-fructose as a furanose ring. Models for the binding sites of GLUT 2, 3 and 4 are presented.

Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct C-glycosylation

2020 ◽  
Vol 56 (34) ◽  
pp. 4712-4715 ◽  
Author(s):  
Yu Hidaka ◽  
Noriaki Kiya ◽  
Makoto Yoritate ◽  
Kazuteru Usui ◽  
Go Hirai
Keyword(s):  
Conformationally Constrained ◽  
Glucose Analogues

Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized carbohydrate donor with a carefully designed sphingosine unit afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener.

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