Product Code Database
Glucose (also called dextrose) is a simple sugar with the molecular formula . Glucose is the most abundant monosaccharide, Handbook of Biodegradable Polymers. CRC Press; 4 February 1998. ISBN . p. 275. a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. There it is used to make cellulose in , which is the most abundant carbohydrate.Kenji Kamide: Cellulose and Cellulose Derivatives. Elsevier, 2005, ISBN 978-0-080-45444-3, p. 1. In energy metabolism, Glucose is the most important source of energy in all . Glucose for metabolism is partially stored as a polymer, in plants mainly as starch and amylopectin and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is D-glucose, while L-glucose is produced synthetically in comparably small amounts and is of lesser importance.
Glucose is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. The name glucose derives through the French from the Greek language γλυκός, which means "sweet," in reference to must, the sweet, first press of grapes in the making of wine.Thénard, Gay-Lussac, Biot, and Dumas (1838) "Rapport sur un mémoire de M. Péligiot, intitulé: Recherches sur la nature et les propriétés chimiques des sucres" (Report on a memoir of Mr. Péligiot, titled: Investigations on the nature and chemical properties of sugars), Comptes rendus, 7 : 106–13. From page 109 : "Il résulte des comparaisons faites par M. Péligot, que le sucre de raisin, celui d'amidon, celui de diabètes et celui de miel ont parfaitement la même composition et les mêmes propriétés, et constituent un seul corps que nous proposons d'appeler Glucose (1). … (1) γλευχος, moût, vin doux." It follows from the comparisons made by Mr. Péligot, that the sugar from grapes, that from starch, that from diabetes and that from honey have exactly the same composition and the same properties, and constitute a single substance that we propose to call glucose (1) … (1) γλευχος, must, sweet wine. The suffix "-ose" is a chemical classifier, denoting a carbohydrate.
Since glucose is a basic necessity of many organisms, a correct understanding of its chemical makeup and structure contributed greatly to a general advancement in organic chemistry. This understanding occurred largely as a result of the investigations of Emil Fischer, a German chemist who received the 1902 Nobel Prize in Chemistry for his findings. The synthesis of glucose established the structure of organic material and consequently formed the first definitive validation of Jacobus Henricus van 't Hoff's theories of chemical kinetics and the arrangements of chemical bonds in carbon-bearing molecules. Between 1891 and 1894, Fischer established the stereochemical configuration of all the known sugars and correctly predicted the possible , applying van 't Hoff's theory of asymmetrical carbon atoms. The names initially referred to the natural substances. Their enantiomers were given the same name with the introduction of systematic nomenclatures, taking into account absolute stereochemistry (e.g. Fischer nomenclature, D/L nomenclature).
For the discovery of the metabolism of glucose Otto Meyerhof received the Nobel Prize in Physiology or Medicine in 1922. "Otto Meyerhof - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018. Hans von Euler-Chelpin was awarded the Nobel Prize in Chemistry along with Arthur Harden in 1929 for their "research on the fermentation of sugar and their share of enzymes in this process". "Hans von Euler-Chelpin - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018. "Arthur Harden - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018. In 1947, Bernardo Houssay (for his discovery of the role of the pituitary gland in the metabolism of glucose and the derived carbohydrates) as well as Carl Cori and Gerty Cori (for their discovery of the conversion of glycogen from glucose) received the Nobel Prize in Physiology or Medicine. "Bernardo Houssay - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018. "Carl Cori - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018. "Gerty Cori - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018. In 1970, Luis Leloir was awarded the Nobel Prize in Chemistry for the discovery of glucose-derived sugar nucleotides in the biosynthesis of carbohydrates. "Luis Leloir - Facts - NobelPrize.org". NobelPrize.org. Retrieved on 5 September 2018.
α-D-glucofuranose | β-D-glucofuranose | |
α-D-glucopyranose | β-D-glucopyranose | |
Each of the four carbons C-2 through C-5 is a stereocenter, meaning that its four bonds connect to four different substituents. (Carbon C-2, for example, connects to -(C=O)H, -OH, -H, and -(CHOH)4H.) In D-glucose, these four parts must be in a specific three-dimensional arrangement. Namely, when the molecule is drawn in the Fischer projection, the hydroxyls on C-2, C-4, and C-5 must be on the right side, while that on C-3 must be on the left side.
The positions of those four hydroxyls are exactly reversed in the Fischer diagram of L-Glucose. D- and L-glucose are two of the 16 possible aldohexoses; the other 14 are allose, altrose, galactose, gulose, idose, mannose, and talose, each with two , “D-” and “L-”.
It is important to note that the linear form of glucose makes up less than 0.02 % of the glucose molecules in a water solution. The rest is one of two cyclic forms of glucose that are formed when the hydroxyl group on carbon 5 (C5) bonds to the aldehyde carbon 1 (C1).
The reaction between C-1 and C-5 yields a six-membered heterocycle system called a pyranose, which is a monosaccharide sugar (hence "–ose") containing a derivatised pyran skeleton. The (much rarer) reaction between C-1 and C-4 yields a five-membered furanose ring, named after the cyclic ether furan. In either case, each carbon in the ring has one hydrogen and one hydroxyl attached, except for the last carbon (C-4 or C-5) where the hydroxyl is replaced by the remainder of the open molecule (which is -(C(CH2OH)HOH)-H or -(CHOH)-H, respectively).
The ring-closing reaction makes carbon C-1 Chirality, too, since its four bonds lead to -H, to -OH, to carbon C-2, and to the ring oxygen. These four parts of the molecule may be arranged around C-1 (the anomeric carbon) in two distinct ways, designated by the prefixes "α-" and "β-". When a glucopyranose molecule is drawn in the Haworth projection, the designation "α-" means that the hydroxyl group attached to C-1 and the -CH2OH group at C-5 lies on opposite sides of the ring's plane (a trans arrangement), while "β-" means that they are on the same side of the plane (a cis arrangement). Therefore, the open-chain isomer -glucose gives rise to four distinct cyclic isomers: α--glucopyranose, β--glucopyranose, α--glucofuranose, and β--glucofuranose. These five structures exist in equilibrium and interconvert, and the interconversion is much more rapid with acid catalysis.
The other open-chain isomer -glucose similarly gives rise to four distinct cyclic forms of -glucose, each the mirror image of the corresponding -glucose.
The rings are not planar, but are twisted in three dimensions. The glucopyranose ring (α or β) can assume several non-planar shapes, analogous to the "chair" and "boat" conformations of cyclohexane. Similarly, the glucofuranose ring may assume several shapes, analogous to the "envelope" conformations of cyclopentane.
In the solid state, only the glucopyranose forms are observed, forming colorless crystalline solids that are highly Solubility in water and acetic acid but poorly soluble in methanol and ethanol. They melt at ( α) and ( β), and Decomposition at higher temperatures into carbon and water.
The open-chain form is thermodynamically unstable, and it spontaneously to the cyclic forms. (Although the ring closure reaction could in theory create four- or three-atom rings, these would be highly strained, and are not observed in practice.) In solutions at room temperature, the four cyclic isomers interconvert over a time scale of hours, in a process called mutarotation.. Starting from any proportions, the mixture converges to a stable ratio of α:β 36:64. The ratio would be α:β 11:89 if it were not for the influence of the anomeric effect. Mutarotation is considerably slower at temperatures close to .
Note that the D- prefix does not refer directly to the optical properties of the compound. It indicates that the C-5 chiral center has the same handedness as that of D-glyceraldehyde (which was so labeled because it is dextrorotatory). The fact that D-glucose is dextrorotatory is a combined effect of its four chiral centers, not just of C-5; and indeed some of the other D-aldohexoses are levorotatory.
The conversion between the two anomers can be observed in a polarimeter, since pure α- D- glucose has a specific rotation angle of +112.2 ° · ml · dm−1 · g−1, pure β- D- glucose of +17.5 ° · ml · dm−1 · g-1.Manfred Hesse, Herbert Meier, Bernd Zeeh, Stefan Bienz, Laurent Bigler, Thomas Fox: Spektroskopische Methoden in der organischen Chemie. 8th revised Edition. Georg Thieme, 2011, , p. 34. (german) When equilibrium has been reached after a certain time due to mutarotation, the angle of rotation is +52.7 ° · ml · dm-1 · g-1. By adding acid or base, this transformation is much accelerated. The equilibration takes place via the open-chain aldehyde form.
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Glucose is produced by plants through the photosynthesis using sunlight, water and carbon dioxide and can be used by all living organisms as an energy and carbon source. However, most glucose does not occur in its free form, but in the form of its polymers, i.e. lactose, sucrose, starch and others which are energy reserve substances, and cellulose and chitin, which are components of the cell wall in plants or fungi and , respectively. These polymers are degraded to glucose during food intake by animals, fungi and bacteria using enzymes. All animals are also able to produce glucose themselves from certain precursors as the need arises. Nerve cells, cells of the renal medulla and erythrocytes depend on glucose for their energy production.Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie. Springer-Verlag, 2014, , p. 195. (german) In adult humans, there are about 18 g of glucose,U. Satyanarayana: Biochemistry. Elsevier Health Sciences, 2014, . p. 674. of which about 4 g are present in the blood.D. H. Wasserman: Four grams of glucose. In: American journal of physiology. Endocrinology and metabolism. Volume 296, issue 1, January 2009, p. E11–E21, , , . Approximately 180 to 220 g of glucose are produced in the liver of an adult in 24 hours.
Many of the long-term complications of diabetes (e.g., blindness, kidney failure, and peripheral neuropathy) are probably due to the glycation of proteins or . In contrast, enzyme-regulated addition of sugars to protein is called glycosylation and is essential for the function of many proteins.9780879697709, Cold Spring Harbor Laboratories Press. . ISBN 9780879697709
In order to get into or out of cell membranes of cells and membranes of cell compartments, glucose requires special transport proteins from the major facilitator superfamily. In the small intestine (more precisely, in the jejunum),Harold A. Harper: Medizinische Biochemie. Springer-Verlag, 2013, , p. 641. (german) glucose is taken up into the intestinal with the help of glucose transportersA. M. Navale, A. N. Paranjape: Glucose transporters: physiological and pathological roles. In: Biophysical Reviews. Volume 8, issue 1, March 2016, p. 5–9, , , . via a secondary active transport mechanism called sodium ion-glucose symport via the sodium/glucose cotransporter 1. The further transfer occurs on the basolateral side of the intestinal epithelial cells via the glucose transporter GLUT2, as well as their uptake into hepatocyte, , cells of the islets of Langerhans, nerve cells, and .B. Thorens: GLUT2, glucose sensing and glucose homeostasis. In: Diabetologia. Volume 58, issue 2, February 2015, p. 221–232, , . Glucose enters the liver via the vena portae and is stored there as a cellular glycogen. In the liver cell, it is Phosphorylation by glucokinase at position 6 to glucose-6-phosphate, which can not leave the cell. With the help of glucose-6-phosphatase, glucose-6-phosphate is converted back into glucose exclusively in the liver, if necessary, so that it is available for maintaining a sufficient blood glucose concentration. In other cells, uptake happens by passive transport through one of the 14 GLUT proteins. In the other cell types, phosphorylation occurs through a hexokinase, whereupon glucose can no longer diffuse out of the cell.
The glucose transporter GLUT1 is produced by most cell types and is of particular importance for nerve cells and pancreatic Beta cell. GLUT3 is highly expressed in nerve cells. Glucose from the bloodstream is taken up by GLUT4 from muscle cells (of the skeletal muscleS. Huang, M. P. Czech: The GLUT4 glucose transporter. In: Cell metabolism. Volume 5, issue 4, April 2007, p. 237–252, , . and heart muscle) and .R. Govers: Cellular regulation of glucose uptake by glucose transporter GLUT4. In: Advances in Clinical Chemistry. Volume 66, 2014, p. 173–240, . GLUT14 is formed exclusively in testes. Excess glucose is broken down and converted into fatty acids, which are stored as . In the , glucose in the urine is absorbed via SGLT1 and SGLT2 in the apical cell membranes and transmitted via GLUT2 in the basolateral cell membranes.C. Ghezzi, D. D. Loo, E. M. Wright: Physiology of renal glucose handling via SGLT1, SGLT2 and GLUT2. In: Diabetologia. August 2018, , . About 90% of kidney glucose reabsorption is via SGLT2 and about 3% via SGLT1.S. B. Poulsen, R. A. Fenton, T. Rieg: Sodium-glucose cotransport. In: Current opinion in nephrology and hypertension. Volume 24, issue 5, September 2015, p. 463–469, , , .
The metabolic pathway that begins with molecules containing two to four carbon atoms (C) and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms. The smaller starting materials are the result of other metabolic pathways. Ultimately almost all come from the assimilation of carbon dioxide in plants during photosynthesis.Donald Voet, Judith G. Voet: Biochemistry, 4th Edition. John Wiley & Sons, 2010, . p. 359. The free energy of formation of α-D-glucose is 917.2 kilojoules per mole.Donald Voet, Judith G. Voet: Biochemistry, 4th Edition. John Wiley & Sons, 2010, . p. 59. In humans, gluconeogenesis occurs in the liver and kidney,Leszek Szablewski: Glucose Homeostasis and Insulin Resistance. Bentham Science Publishers, 2011, , p. 46. but also in other cell types. In the liver about 150 g of glycogen are stored, in skeletal muscle about 250 g.Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie. Springer-Verlag, 2014, , p. 389. (german) However, the glucose released in muscle cells upon cleavage of the glycogen can not be delivered to the circulation because glucose is phosphorylated by the hexokinae, and a glucose-6-phosphatase is not expressed to remove the phosphate group. Unlike for glucose, there is no transport protein for glucose-6-phosphate. Gluconeogenesis allows the organism to build up glucose from other metabolites, including lactic acid or certain amino acids, while consuming energy. The renal can also produce glucose.
In other living organisms, other forms of fermentation can occur. The bacterium Escherichia coli can grow on nutrient media containing glucose as the sole carbon source. In some bacteria and, in modified form, also in archaea, glucose is degraded via the Entner-Doudoroff pathway.Entner, N. und Doudoroff, M. (1952): Glucose and gluconic acid oxidation of Pseudomonas saccharophila. In: J Biol Chem. Volume 196, issue 2, p. 853–862; ; PDF.
Use of glucose as an energy source in cells is by either aerobic respiration, anaerobic respiration, or fermentation. The first step of glycolysis is the phosphorylation of glucose by a hexokinase to form glucose 6-phosphate. The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged phosphate group prevents glucose 6-phosphate from easily crossing the cell membrane. Furthermore, addition of the high-energy phosphate group activates glucose for subsequent breakdown in later steps of glycolysis. At physiological conditions, this initial reaction is irreversible.
In anaerobic respiration, one glucose molecule produces a net gain of two ATP molecules (four ATP molecules are produced during glycolysis through substrate-level phosphorylation, but two are required by enzymes used during the process). In aerobic respiration, a molecule of glucose is much more profitable in that a maximum net production of 30 or 32 ATP molecules (depending on the organism) through oxidative phosphorylation is generated.
Tumor cells often grow comparatively quickly and consume an above-average amount of glucose by glycolysis,A. Annibaldi, C. Widmann: Glucose metabolism in cancer cells. In: Current Opinion in Clinical Nutrition and Metabolic Care (2010). Volume 13, issue 4, p. 466–470, , . which leads to the formation of lactate, the end product of fermentation in mammals, even in the presence of oxygen. This effect is called Warburg Effect. For the increased uptake of glucose in tumors various SGLT and GLUT are overly produced.L. Szablewski: Expression of glucose transporters in cancers. In: Biochimica et biophysica acta. Volume 1835, issue 2, April 2013, p. 164–169, , .K. Adekola, S. T. Rosen, M. Shanmugam: Glucose transporters in cancer metabolism. In: Current opinion in oncology. Volume 24, issue 6, 2012, p. 650–654, , . In yeast, ethanol is fermented at high glucose concentrations, even in the presence of oxygen (which normally leads to respiration but not to fermentation). This effect is called the Crabtree effect.
Glucose supplies almost all the energy for the brain, so its availability influences psychological processes. When Hypoglycaemia, psychological processes requiring mental effort (e.g., self-control, effortful decision-making) are impaired. In the brain, which is dependent on glucose as the major source of energy, the glucose concentration is usually 4 to 6 mM (5 mM equals 90 mg / dL), but decreases to 2 to 3 mM when fasting. Confusion occurs below 1 mM and coma at lower levels.
The glucose in the blood is called blood sugar. Blood sugar levels are regulated by glucose-binding nerve cells in the hypothalamus.L. L. Koekkoek, J. D. Mul, S. E. la Fleur: Glucose-Sensing in the Reward System. In: Frontiers in neuroscience. Volume 11, 2017, p. 716, , , . In addition, glucose in the brain binds to glucose receptors of the reward system in the nucleus accumbens. The binding of glucose to the sweet receptor on the tongue induces a release of various hormones of energy metabolism, either through glucose or through other sugars, leading to an increased cellular uptake and lower blood sugar levels.R. M. Tucker, S. Y. Tan: Do non-nutritive sweeteners influence acute glucose homeostasis in humans? A systematic review. In: Physiology & behavior. Volume 182, December 2017, p. 17–26, , . Artificial sweeteners do not lower blood sugar levels.
The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dl of blood (4 to 5.5 mM). In blood plasma, the measured values are about 10-15 % higher. In addition, the values in the artery blood are higher than the concentrations in the vein blood since glucose is absorbed into the tissue during the passage of the capillary bed. Also in the capillary blood, which is often used for blood sugar determination, the values are sometimes higher than in the venous blood. The glucose content of the blood is regulated by the hormones insulin, incretin and glucagon.S. E. La Fleur, E. Fliers, A. Kalsbeek: Neuroscience of glucose homeostasis. In: Handbook of clinical neurology. Volume 126, 2014, p. 341–351, , . Insulin lowers the glucose level, glucagon increases it. Furthermore, the hormones adrenaline, thyroxine, , somatotropin and adrenocorticotropin lead to an increase in the glucose level. In addition, there is also a hormone-independent regulation, which is referred to as glucose autoregulation.P. H. Bisschop, E. Fliers, A. Kalsbeek: Autonomic regulation of hepatic glucose production. In: Comprehensive Physiology. Volume 5, issue 1, 2015, p. 147–165, , . After food intake the blood sugar concentration increases. Values over 180 mg/dl in venous whole blood are pathological and are termed hyperglycemia, values below 40 mg/dl are termed hypoglycaemia.W. A. Scherbaum, B. M. Lobnig, In: Hans-Peter Wolff, Thomas R. Weihrauch: Internistische Therapie 2006, 2007. 16th Edition. Elsevier, 2006, , p. 927, 985. (german) When needed, glucose is released into the bloodstream by glucose-6-phosphatase from glucose-6-phosphate originating from liver and kidney glycogen, thereby regulating the homeostasis of blood glucose concentration. In , the blood glucose concentration is lower (60 mg/dL in cattle and 40 mg/dL in sheep), because the carbohydrates are converted more by their gut flora into short-chain fatty acids.Harold A. Harper: Medizinische Biochemie. Springer-Verlag, 2013, , p. 294.
Some glucose is converted to lactic acid by , which is then utilized as an energy source by brain cells; some glucose is used by intestinal cells and erythrocytes, while the rest reaches the liver, adipose tissue and muscle cells, where it is absorbed and stored as glycogen (under the influence of insulin). Liver cell glycogen can be converted to glucose and returned to the blood when insulin is low or absent; muscle cell glycogen is not returned to the blood because of a lack of enzymes. In Adipocyte, glucose is used to power reactions that synthesize some fat types and have other purposes. Glycogen is the body's "glucose energy storage" mechanism, because it is much more "space efficient" and less reactive than glucose itself.
As a result of its importance in human health, glucose is an analyte in that are common medical . Eating or fasting prior to taking a blood sample has an effect on analyses for glucose in the blood; a high fasting glucose blood sugar level may be a sign of prediabetes or diabetes mellitus.
The glycemic index is an indicator of the speed of resorption and conversion to blood glucose levels from ingested carbohydrates, measured as the area under the curve of blood glucose levels after consumption in comparison to glucose (glucose is defined as 100).Richard A. Harvey, Denise R. Ferrier: Biochemistry. 5th Edition, Lippincott Williams & Wilkins, 2011, , p. 366. The clinical importance of the glycemic index is controversial,U Satyanarayana: Biochemistry. Elsevier Health Sciences, 2014, , p. 508. as foods with high fat contents slow the resorption of carbohydrates and lower the glycemic index, e.g. ice cream. An alternative indicator is the insulin index,S. H. Holt, J. C. Miller, P. Petocz: An insulin index of foods: the insulin demand generated by 1000-kJ portions of common foods. In: The American journal of clinical nutrition. Volume 66, issue 5, November 1997, p. 1264–1276, , . measured as the impact of carbohydrate consumption on the blood insulin levels. The glycemic load is an indicator for the amount of glucose added to blood glucose levels after consumption, based on the glycemic index and the amount of consumed food.
Other than its direct use as a monomer, glucose can be broken down to synthesize a wide variety of other biomolecules. This is important, as glucose serves both as a primary store of energy and as a source of organic carbon. Glucose can be broken down and converted into lipids. It is also a precursor for the synthesis of other important molecules such as vitamin C (ascorbic acid). In living organisms, glucose is converted to several other chemical compounds that are the starting material for various metabolic pathways. Among them, all other monosaccharidesPeter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie. Springer-Verlag, 2014, , p. 27. (german) such as fructose (via the polyol pathway),Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie. Springer-Verlag, 2014, , p. 199, 200. (german) mannose (the epimer of glucose at position 2), galactose (the epimer at position 4), fucose, various uronic acids and the are produced from glucose.Peter C. Heinrich: Löffler/Petrides Biochemie und Pathobiochemie. Springer-Verlag, 2014, , p. 214. (german) In addition to the phosphorylation to glucose-6-phosphate, which is part of the glycolysis, glucose can be oxidized during its degradation to glucono-1,5-lactone. Glucose is used in some bacteria as a building block in the trehalose or the dextran biosynthesis and in animals as a building block of glycogen. Glucose can also be converted from bacterial xylose isomerase to fructose. In addition, glucose produce all nonessential , such as mannitol and sorbitol, , cholesterol and . Finally, glucose is used as a building block in the glycosylation of proteins to , , , and other substances (catalyzed by glycosyltransferases) and can be cleaved from them by .
To monitor the body's response to blood glucose-lowering therapy, glucose levels can be measured. Blood glucose monitoring can be performed by multiple methods, such as the fasting glucose test which measures the level of glucose in the blood after 8 hours of fasting. Another test is the 2-hour glucose tolerance test (GTT) – for this test, the person has a fasting glucose test done, then drinks a 75-gram glucose drink and is retested. This test measures the ability of the person's body to process glucose. Over time the blood glucose levels should decrease as insulin allows it to be taken up by cells and exit the blood stream.
| +Table 1. Sugar content of selected common plant foods (g/100g) "Food Composition Databases Show Foods List". ndb.nal.usda.gov. |
| 19.9 |
| 63.5 |
| 20.0 |
| 0.15 |
| 1 |
| 50.4 |
| 56.7 |
| 8.0 |
| 60.8 |
| 16.2 |
| 96.2 |
| 77 |
| 0.0 |
| 14.3 |
| 60.3 |
| traces |
| high |
| high |
| 15.0 |
The carbohydrate figure is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".
All data with a unit of g (gram) are based on 100 g of a food item.
Many crops can be used as the source of starch. Maize, rice, wheat, cassava, potato, barley, sweet potato,Alan Davidson: The Oxford Companion to Food. OUP Oxford, 2014, , p. 527. corn husk and sago are all used in various parts of the world. In the United States, corn starch (from maize) is used almost exclusively. Some commercial glucose occurs as a component of invert sugar, a roughly 1:1 mixture of glucose and fructose that is produced from sucrose. In principle, cellulose could be hydrolysed to glucose, but this process is not yet commercially practical.
In addition, various organic acids can be biotechnologically produced from glucose, for example by fermentation with Clostridium thermoaceticum to produce acetic acid, with Penicilium notatum for the production of araboascorbic acid, with Rhizopus delemar for the production of fumaric acid, with Aspergillus niger for the production of gluconic acid, with Candida brumptii to produce isocitric acid, with Aspergillus terreus for the production of itaconic acid, with Pseudomonas fluorescens for the production of 2-ketogluconic acid, with Gluconobacter suboxydans for the production of 5-ketogluconic acid, with Aspergillus oryzae for the production of kojic acid, with Lactobacillus delbrueckii for the production of lactic acid, with Lactobacillus brevis for the production of malic acid, with Propionibacter shermanii for the production of propionic acid, with Pseudomonas aeruginosa for the production of pyruvic acid and with Gluconobacter suboxydans for the production of tartaric acid.James A. Kent: Riegel's Handbook of Industrial Chemistry. Springer Science & Business Media, 2013, , p. 938.
Conversion to fructose
In the USA almost exclusively corn (more precisely: corn syrup) is used as glucose source for the production of isoglucose, which is a mixture of glucose and fructose, since fructose has a higher sweetening power — with same physiological calorific value of 374 kilocalories per 100 g. The annual world production of isoglucose is eight million tonnes (as of 2011). When made from corn syrup, the final product is high fructose corn syrup (HFCS).
Commercial usage
Glucose is mainly used for the production of fructose and in the production of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel. Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass). In the neighboring country Mexico, on the other hand, cane sugar is used in the soft drink as a sweetener, which has a higher sweetening power.Kevin Pang: Mexican Coke a hit in U.S. In: Seattle Times, October 29, 2004. In addition, glucose syrup is used, inter alia, in the production of confectionery such as candy, toffee and fondant icing.Steve T. Beckett: Beckett's Industrial Chocolate Manufacture and Use. John Wiley & Sons, 2017, , p. 82. Typical chemical reactions of glucose when heated under water-free conditions are the caramelization and, in presence of amino acids, the maillard reaction.
Analysis
Specifically, when a glucose molecule is to be detected at a certain position in a larger molecule, nuclear magnetic resonance spectroscopy, X-ray crystallography analysis or lectin immunostaining is performed with concanavalin A reporter enzyme conjugate (that binds only glucose or mannose).
Classical qualitative detection reactions
These reactions have only historical significance:
Fehling Test
The Fehling test is a classic method for the detection of aldoses.H. Fehling: Quantitative Bestimmung des Zuckers im Harn. In: Archiv für physiologische Heilkunde (1848), volume 7, p. 64–73. (german) Due to mutarotation, glucose is always present to a small extent as an open-chain aldehyde. By adding the Fehling reagents (Fehling (I) solution and Fehling (II) solution), the aldehyde group is oxidized to a carboxylic acid, while the Cu2+ tartrate complex is reduced to Cu+ and forming a brick red precipitate (Cu2O).
Tollens Test
In the Tollens test, after addition of ammoniacal Silver nitrate to the sample solution, Ag+ is reduced by glucose to elemental silver.B. Tollens: Über ammon-alkalische Silberlösung als Reagens auf Aldehyd. In Berichte der Deutschen Chemischen Gesellschaft (1882), volume 15, p. 1635–1639. (german)
Barfoed test
In Barfoed's test,C. Barfoed: Über die Nachweisung des Traubenzuckers neben Dextrin und verwandten Körpern. In: Zeitschrift für Analytische Chemie (1873), volume 12, issue 1, p. 27, . (german) a solution of dissolved copper acetate, sodium acetate and acetic acid is added to the solution of the sugar to be tested and subsequently heated in a water bath for a few minutes. Glucose and other monosaccharides rapidly produce a reddish color and reddish brown copper(I) oxide (Cu2O).
Nylander's Test
As a reducing sugar, glucose reacts in the Nylander's test.Emil Nylander: Über alkalische Wismuthlösung als Reagens auf Traubenzucker im Harne, Zeitschrift für physiologische Chemie. Volume 8, Issue 3, 1884, p. 175–185 Abstract. (german)
Other tests
Upon heating a dilute potassium hydroxide solution with glucose to 100 °C, a strong reddish browning and a caramel-like odor develops.Georg Schwedt: Zuckersüße Chemie. John Wiley & Sons, 2012, , p. 102. (german) Concentrated sulfuric acid dissolves dry glucose without blackening at room temperature forming sugar sulfuric acid. In a yeast solution, alcoholic fermentation produces carbon dioxide in the ratio of 2.0454 molecules of glucose to one molecule of Carbon dioxide. Glucose forms a black mass with stannous chloride. In an ammoniacal silver solution, glucose (as well as lactose and dextrin) leads to the deposition of silver. In an ammoniacal lead acetate solution, white lead glycoside is formed in the presence of glucose, which becomes less soluble on cooking and turns brown. In an ammoniacal copper solution, yellow copper oxide hydrate is formed with glucose at room temperature, while red copper oxide is formed during boiling (same with dextrin, except for with an ammoniacal copper acetate solution). With Hager's reagent, glucose forms mercury oxide during boiling. An alkaline bismuth solution is used to precipitate elemental, black-brown bismuth with glucose. Glucose boiled in an ammonium molybdate solution turns the solution blue. A solution with indigo carmine and sodium carbonate destains when boiled with glucose.
Instrumental Quantification
Refractometry and Polarimetry
In concentrated solutions of glucose with a low proportion of other carbohydrates, its concentration can be determined with a polarimeter. For sugar mixtures, the concentration can be determined with a refractometer, for example in the Oechsle scale determination in the course of the production of wine.
Photometric enzymatic methods in solution
The enzyme glucose oxidase (GOx) converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen. Another enzyme, peroxidase, catalyzes a chromogenic reaction (Trinder reaction)P. Trinder: Determination of glucose in blood using glucose oxidase with an alternative oxygen acceptor. In: Annals of Clinical Biochemistry. 6, 1969, p. 24–27; . of phenol with 4-aminoantipyrine to a purple dye.
Photometric Test Strip Method
The test strip method employs the above-mentioned enzymatic conversion of glucose to gluconic acid to form hydrogen peroxide. The reagents are immobilised on a polymer matrix, the so-called test strip, which assumes a more or less intense color. This can be measured reflectometrically at 510 nm with the aid of an LED-based handheld photometer. This allows for routine blood sugar determination by laymen. In addition to the reaction of phenol with 4-aminoantipyrine, new chromogenic reactions have been developed that allow photometry at higher wavelengths (550 nm, 750 nm).M. Mizoguchi, M. Ishiyama, M. Shiga, K. Sasamoto: Water-soluble chromogenic reagent for colorimetric detection of hydrogen peroxide – an alternative to 4-aminoantipyrine working at a long wavelength. In: Analytical Communications. 35, 1998, p. 71–73; .
Amperometric glucose sensor
The electroanalysis of glucose is also based on the enzymatic reaction mentioned above. The produced hydrogen peroxide can be amperometrically quantified by anodic oxidation at a potential of 600 mV.J. Wang: Electrochemical Glucose Biosensors. In: Chem. Rev. (2008), volume 108, p. 814–825; . The GOx is immobilised on the electrode surface or in a membrane placed close to the electrode. Precious metals such as platinum or gold are used in electrodes, as well as carbon nanotube electrodes, which e.g. are doped with boron.X. Chen, J. Chen, Ch. Deng, Ch. Xiao, Y. Yang, Z. Nie, S. Yao: Amperometric glucose biosensor based on boron-doped carbon nanotubes modified electrode. In: Talanta (2008), volume 76, p. 763–767. . . Cu-CuO nanowires are also used as enzyme-free amperometric electrodes. This way a detection limit of 50 µmol/L has been achieved.G. Wang, Y. Wei, W. Zhang, X. Zhang, B. Fang, L. Wang: Enzyme-free amperometric sensing of glucose using Cu-CuO nanowire composites. In: Microchimica Acta. Volume 168, 2010, p. 87–92; . A particularly promising method is the so-called "enzyme wiring". In this case, the electron flowing during the oxidation is transferred directly from the enzyme via a molecular wire to the electrode.T. J. Ohara, R. Rajagopaian, A. Heller: „Wired“ Enzyme Electrodes for Amperometric Determination of Glucose or Lactate in the Presence of Interfering Substances. In: Anal. Chem. (1994), volume 66, p. 2451–2457; ; .
Other sensory methods
There are a variety of other chemical sensors for measuring glucose.S. M. Borisov, O. S. Wolfbeis: Optical Biosensors. In: Chem. Rev. 108, 2008, p. 423–461; ; .S. Ferri, K. Kojima, K. Sode: Review of glucose oxidases and glucose dehydrogenases: a bird's eye view of glucose sensing enzymes. In: Journal of diabetes science and technology. Volume 5, issue 5, September 2011, p. 1068–1076, , , . Given the importance of glucose analysis in the life sciences, numerous optical probes have also been developed for saccharides based on the use of boronic acids,H. S. Mader, O. S. Wolfbeis: Boronic acid based probes for microdetermination of saccharides and glycosylated biomolecules. In: Microchimica Acta. 162, 2008, p. 1–34; . which are particularly useful for intracellular sensory applications where other (optical) methods are not or only conditionally usable. In addition to the organic boronic acid derivatives, which often bind highly specifically to the 1,2-diol groups of sugars, there are also other probe concepts classified by functional mechanisms which use selective glucose-binding proteins (e.g. concanavalin A) as a receptor. Furthermore, methods were developed which indirectly detect the glucose concentration via the concentration of metabolised products, e.g. by the consumption of oxygen using fluorescence-optical sensors.O. S. Wolfbeis, I. Oehme, N. Papkovskaya, I. Klimant: Sol-Gel based Glucose Biosensors Employing Optical Oxygen Transducers, and a Method for Compensating for Variable Oxygen Background. In: Biosensors & Bioelectronics. 15, 2000, p. 69–76; . Finally, there are enzyme-based concepts that use the intrinsic absorbance or fluorescence of (fluorescence-labeled) enzymes as reporters.
Copper iodometry
Glucose can be quantified by copper iodometry.A. L. Galant, R. C. Kaufman, J. D. Wilson: Glucose: Detection and analysis. In: Food Chemistry. Volume 188, December 2015, p. 149–160, , .
Chromatographic methods
In particular, for the analysis of complex mixtures containing glucose, e.g. in honey, chromatographic methods such as high performance liquid chromatography and gas chromatography are often used in combination with mass spectrometry.M. L. Sanz, J. Sanz, I. Martínez-Castro: Gas chromatographic-mass spectrometric method for the qualitative and quantitative determination of disaccharides and trisaccharides in honey. In: Journal of Chromatography A, volume 1059, issue 1–2, 2004, p. 143–148; . Taking into account the isotope ratios, it is also possible to reliably detect honey adulteration by added sugars with these methods.A. I. Cabañero, J. L. Recio, M. Rupérez: Liquid chromatography coupled to isotope ratio mass spectrometry: a new perspective on honey adulteration detection. In: J Agric Food Chem. 54(26), 27 December 2006, p. 9719–9727; . Derivatisation using silylation reagents is commonly used.M. Becker, F. Ler, T. Rosenau, A. Potthast: Ethoximation-silylation approach for mono- and disaccharide analysis and characterization of their identification parameters by GC/MS. In: Talanta. Volume 115, 2013, p. 642–651; . Also, the proportions of di- and trisaccharides can be quantified.
In vivo analysis
Glucose uptake in cells of organisms is measured with 2-deoxy-D-glucose or fluorodeoxyglucose.Donard Dwyer: Glucose Metabolism in the Brain. Academic Press, 2002, , p. XIII. (18F)fluorodeoxyglucose is used as a tracer in positron emission tomography in oncology and neurology,Gesellschaft Deutscher Chemiker: | wayback=20100331071121 Anlagen zum Positionspapier der Fachgruppe Nuklearchemie, February 2000. where it is by far the most commonly used diagnostic agent.Simone Maschauer, Olaf Prante: Sweetening Pharmaceutical Radiochemistry by 18F-Fluoroglycosylation: A Short Review, in: BioMed Research International, Volume 2014, Article-ID 214748; ; ; .
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