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20-September-2008 09:55:48 - Glucose Glucose IUPAC name 6-hydroxymethyloxane -2,3,4,5-tetrol OR 2R,3R,4S,5R,6R-6 -hydroxymethyltetrahydro -2H-pyran-2,3,4,5-tetraol Other names Dextrose Identifiers Abbreviations Glc CAS number 50-99-7 D-glucose 921-60-8 L-glucose PubChem 5793 SMILES CC1CCCCO1OOOOO Properties Molecular formula C6H12O6 Molar mass 180.16 g mol-1 Density 1.54 g cm-3 Melting point α-D-glucose: 146°C β-D-glucose: 150°C Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Glucose Glc, a monosaccharide or simple sugar also known as grape sugar, is an important carbohydrate in biology. The living cell uses it as a source of energy and metabolic intermediate. Glucose is one of the main products of photosynthesis and starts cellular respiration in both prokaryotes and eukaryotes. The name comes from the Greek word glykys γλυκÏ?Ï‚, meaning sweet, plus the suffix -ose which denotes a sugar. Two stereoisomers of the aldohexose sugars are known as glucose, only one of which D-glucose is biologically active. This form D-glucose is often referred to as dextrose monohydrate, or, especially in the food industry, simply dextrose from dextrorotatory glucose1. This article deals with the D-form of glucose. The mirror-image of the molecule, L-glucose, cannot be metabolized by cells in the biochemical process known as glycolysis. Contents 1 Structure 1.1 Isomers 1.2 Rotamers 2 Properties and energy content 3 Production 3.1 Natural 3.2 Commercial 4 Function 4.1 As an energy source 4.2 Glucose in glycolysis 4.3 As a precursor 5 Sources and absorption 6 See also 7 References 8 External links Structure Glucose C6H12O6 contains six carbon atoms, one of which is part of an aldehyde group, and is therefore referred to as an aldohexose. In solution, the glucose molecule can exist in an open-chain acyclic form and a ring cyclic form in equilibrium. The cyclic form is the result of a covalent bond between the aldehyde C atom and the C-5 hydroxyl group to form a six-membered cyclic hemiacetal. At pH 7 the cyclic form is predominant. In the solid phase, glucose assumes the cyclic form. Because the ring contains five carbon atoms and one oxygen atom, which resembles the structure of pyran, the cyclic form of glucose is also referred to as glucopyranose. In this ring, each carbon is linked to a hydroxyl side group with the exception of the fifth atom, which links to a sixth carbon atom outside the ring, forming a CH2OH group. Glucose is commonly available in the form of a white substance or as a solid crystal. It can also be dissolved in water as an aqueous solution. Isomers Aldohexose sugars have 4 chiral centers giving 24 = 16 stereoisomers. These are split into two groups, L and D, with 8 sugars in each. Glucose is one of these sugars, and L-glucose and D-glucose are two of the stereoisomers. Only 7 of these are found in living organisms, of which D-glucose Glu, D-galactose Gal, and D-mannose Man are the most important. These eight isomers including glucose itself are related as diastereoisomers and belong to the D series. An additional asymmetric center at C-1 called the anomeric carbon atom is created when glucose cyclizes hi and two ring structures called anomers are formed as α-glucose and β-glucose. These anomers differ structurally by the relative positioning of the hydroxyl group linked to C-1, and the group at C-6 which is termed the reference carbon. When D-glucose is drawn as a Haworth projection or in the standard chair conformation, the designation α means that the hydroxyl group attached to C-1 is positioned trans to the -CH2OH group at C-5, while β means it is cis. Another popular method of distinguishing α from β is by observing whether the C-1 hydroxyl is below or above the plane of the ring; but this method is an inaccurate definition, and may fail if the glucose ring is drawn upside down or in an alternative chair conformation. The α and β forms interconvert over a timescale of hours in aqueous solution, to a final stable ratio of α:β 36:64, in a process called mutarotation.2 The Fischer projection of the chain form of D-glucose The chain form of D-glucose α-D- glucopyranose β-D- glucopyranose Chain form: ball-and-stick model Chain form: space-filling model α-D- glucopyranose β-D- glucopyranose Rotamers Within the cyclic form of glucose, rotation may occur around the O6-C6-C5-O5 torsion angle, termed the ω-angle, to form three rotamer conformations as shown in the diagram below. Referring to the orientations of the ω-angle and the O6-C6-C5-C4 angle the three stable staggered rotamer conformations are termed gauche-gauche gg, gauche-trans gt and trans-gauche tg. For methyl α-D-glucopyranose at equilibrium the ratio of molecules in each rotamer conformation is reported as 57:38:5 gg:gt:tg.3 This tendency for the ω-angle to prefer to adopt a gauche conformation is attributed to the gauche effect. Rotamer conformations of α-D-glucopyranose Rotamer conformations of α-D-glucopyranose Properties and energy content The Gibbs free energy of formation of solid glucose is -909 kJ/mol and the enthalpy of formation is -1007 kJ/mol. The heat of combustion with liquid water in the product is about 2803 kJ/mol, or 3.72 kcal per gram. The ΔG change of Gibbs free energy for this combustion is about -2880 kJ/mol. Upon heating, glucose, like any carbohydrate, will undergo pyrolysis carbonization yielding steam and a char consisting mostly of carbon. This reaction is exothermic, releasing about 0.237 kcal per gram. Production Natural Glucose is one of the products of photosynthesis in plants and some prokaryotes. In animals and fungi, glucose is the result of the breakdown of glycogen, a process known as glycogenolysis. In plants the breakdown substrate is starch. In animals, glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. Commercial Glucose is produced commercially via the enzymatic hydrolysis of starch. Many crops can be used as the source of starch. Maize, rice, wheat, potato, cassava, arrowroot, and sago are all used in various parts of the world. In the United States, cornstarch from maize is used almost exclusively. This enzymatic process has several stages. In the gelatinization stage, a slurry of starch is heated to 105 °C, and the enzyme, α-amylase, is added. In the liquefaction stage, the mixture is held at 95 °C for 2 hours. In the last stage, known as saccharification, the partially hydrolyzed starch is completely hydrolyzed to glucose using the glucoamylase enzyme from the fungus Aspergillus niger. Typical reaction conditions are pH 4.0-4.5, 60 °C, and a carbohydrate concentration of 30-35% by weight. Under these conditions, starch can be converted to glucose at 96-97% glucose, glucose syrup over 1-4 days.4 In some variations on this process, the liquefaction stage is carried out at 130 °C or even hotter.citation needed This heat treatment improves the solubility of starch in water, yielding a more concentrated syrup, but deactivates the enzyme, and fresh enzyme must be added to the mixture after each heating. Higher glucose yields can be obtained using more dilute solutions, but this approach requires larger reactors and processing a greater volume of water, and is not generally economical. ultimately, the resulting glucose solution is then purified by filtration and concentrated in a multiple-effect evaporator. Solid D-glucose is then produced by repeated crystallizations. Glucose Glucose tablets Function Scientists can speculate on the reasons why glucose, and not another monosaccharide such as fructose Fru, is so widely used in evolution, the ecosystem, and metabolism. Glucose can form formaldehyde under abiotic conditions, so it may well have been available to primitive biochemical systems. Probably more important to advanced life is the low tendency of glucose, by comparison to other hexose sugars, to non-specifically react with the amino groups of proteins. This reaction glycation reduces or destroys the function of many enzymes. The low rate of glycation is due to glucose's preference for the less reactive cyclic isomer. Nevertheless, 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 lipids. In contrast, enzyme-regulated addition of glucose to proteins by glycosylation is often essential to their function. As an energy source Glucose is an ubiquitous fuel in biology. It is used as an energy source in most organisms, from bacteria to humans. Use of glucose may be by either aerobic or anaerobic respiration fermentation. Carbohydrates are the human body's key source of energy, through aerobic respiration, providing approximately 3.75 kilocalories 16 kilojoules of food energy per gram.5 Breakdown of carbohydrates e.g. starch yields mono- and disaccharides, most of which is glucose. Through glycolysis and later in the reactions of the Citric acid cycle TCAC, glucose is oxidized to eventually form CO2 and water, yielding energy, mostly in the form of ATP. The insulin reaction, and other mechanisms, regulate the concentration of glucose in the blood. A high fasting blood sugar level is an indication of prediabetic and diabetic conditions. Glucose is a primary source of energy for the brain, and hence its availability influences psychological processes. When glucose is low, psychological processes requiring mental effort e.g., self-control, effortful decision-making are impaired.6789 Glucose in glycolysis α-D-Glucose Hexokinase α-D-Glucose-6-phosphate image:Glucose_wpmp.png image:Glucose-6-phosphate_wpmp.png ATP ADP Compound C00031 at KEGG Pathway Database. Enzyme 2.7.1.1 at KEGG Pathway Database. Compound C00668 at KEGG Pathway Database. Reaction R01786 at KEGG Pathway Database. Use of glucose as an energy source in cells is via aerobic or anaerobic respiration. Both of these start with the early steps of the glycolysis metabolic pathway. The first step of this is the phosphorylation of glucose by hexokinase to prepare it for later breakdown to provide energy. The major reason for the immediate phosphorylation of glucose by a hexokinase is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. Irreversible first steps of a metabolic pathway are common for regulatory purposes. As a precursor Glucose is critical in the production of proteins and in lipid metabolism. Also, in plants and most animals, it is a precursor for vitamin C ascorbic acid production. It is modified for use in these processes by the glycolysis pathway. Glucose is used as a precursor for the synthesis of several important substances. Starch, cellulose, and glycogen animal starch are common glucose polymers polysaccharides. Lactose, the predominant sugar in milk, is a glucose-galactose disaccharide. In sucrose, another important disaccharide, glucose is joined to fructose. These synthesis processes also rely on the phosphorylation of glucose through the first step of glycolysis. Sources and absorption All major dietary carbohydrates contain glucose, either as their only building block, as in starch and glycogen, or together with another monosaccharide, as in sucrose and lactose. In the lumen of the duodenum and small intestine, the oligo- and polysaccharides are broken down to monosaccharides by the pancreatic and intestinal glycosidases. Glucose is then transported across the apical membrane of the enterocytes by SLC5A1, and later across their basal membrane by SLC2A2.10 Some of the glucose goes directly toward fueling brain cells and erythrocytes, while the rest makes its way to the liver and muscles, where it is stored as glycogen, and to fat cells, where it can be used to power reactions which synthesize some fats. Glycogen is the body's auxiliary energy source, tapped and converted back into glucose when there is need for energy. See also Blood glucose or Blood Sugar HbA1c DMF potential glucose-based biofuel Glycation Glycosylation Photosynthesis Fructose Beriberi - vitamin deficiency affecting ability to convert carbohydrates into glucose v d e Glycolysis Metabolic Pathway Glucose Hexokinase Glucose-6-phosphate Glucose-6-phosphate isomerase Fructose 6-phosphate 6-phosphofructokinase Fructose 1,6-bisphosphate Fructose bisphosphate aldolase Dihydroxyacetone phosphate Glyceraldehyde 3-phosphate Triosephosphate isomerase Glyceraldehyde 3-phosphate Glyceraldehyde-3-phosphate dehydrogenase ATP ADP ATP ADP NAD+ + Pi NADH + H+ + 2 NAD+ + Pi NADH + H+ 1,3-Bisphosphoglycerate Phosphoglycerate kinase 3-Phosphoglycerate Phosphoglycerate mutase 2-Phosphoglycerate Phosphopyruvate hydrataseEnolase Phosphoenolpyruvate Pyruvate kinase Pyruvate Pyruvate dehydrogenase Acetyl-CoA ADP ATP H2O ADP ATP CoA + NAD+ NADH + H+ + CO2 2 2 2 2 2 2 ADP ATP H2O References ^ dextrose - Definition from the Merriam-Webster Online Dictionary ^ McMurry, John 1988. Organic Chemistry. Brooks/Cole, 866. ISBN 0534079687. ^ Kirschner, K.N. Woods, R.J. 2001. Solvent interactions determine carbohydrate conformation. Proc. Natl. Acad. Sci. USA. 98 19: 10541-10545. doi:10.1073/pnas.191362798. PMID 11526221. ^ Martin 2004-12-20. The use of enzymes in starch hydrolysis. London South Bank University. Retrieved on 2008-03-27. ^ CHAPTER 3: CALCULATION OF THE ENERGY CONTENT OF FOODS - ENERGY CONVERSION FACTORS ^ Fairclough, S. H., Houston, K. 2004. A metabolic measure of mental effort. Biological Psychology 66: 177-190. doi:10.1016/j.biopsycho.2003.10.001. PMID 15041139. ^ Gailliot, M.T., Baumeister, R.F., DeWall, C.N., Maner, J.K., Plant, E.A., Tice, D.M., Brewer, L.E., Schmeichel, B.J. 2007. Self-Control relies on glucose as a limited energy source: Willpower is more than a metaphor. Journal of Personality and Social Psychology 92: 325-336. doi:10.1037/0022-3514.92.2.325. PMID 17279852. ^ Gailliot, M.T., Baumeister, R.F. 2007. The physiology of willpower: Linking blood glucose to self-control. Personality and Social Psychology Review 11: 303-327. doi:10.1177/1088868307303030. PMID 18453466. ^ Masicampo, E.J., Baumeister, R.F. 2008. Toward a physiology of dual-process reasoning and judgment: Lemonade, willpower, and expensive rule-based analysis. Psychological Science 19: 255-260. doi:10.1111/j.1467-9280.2008.02077.x. ^ Ferraris, Ronaldo P. 2001. Dietary and developmental regulation of intestinal sugar transport. Biochemical Journal 360 360: 265-276. doi:10.1042/0264-6021:3600265. Retrieved on 2007-12-21. External links Wikimedia Commons has media related to: Glucose EINECS number 200-075-1 D-glucose EINECS number 213-068-3 L-glucose CID 5793 from PubChem D-glucose CID 206 from PubChem L-glucose More on the chemistry and function of glucose in biology at EvoWiki Computational Chemistry Wiki What is Glucose v d e Types of Carbohydrates General: Aldose | Ketose | Pyranose | Furanose Geometry Cyclohexane conformation | Anomer | Mutarotation Monosaccharides Trioses Ketotriose Dihydroxyacetone | Aldotriose Glyceraldehyde Tetroses Ketotetrose Erythrulose | Aldotetroses Erythrose, Threose Pentoses Ketopentose Ribulose, Xylulose Aldopentose Ribose, Arabinose, Xylose, Lyxose Deoxy sugar Deoxyribose Hexoses Ketohexose Psicose, Fructose, Sorbose, Tagatose Aldohexose Allose, Altrose, Glucose, Mannose, Gulose, Idose, Galactose, Talose Deoxy sugar Fucose, Fuculose, Rhamnose Heptose Sedoheptulose Multiple Disaccharides Sucrose | Lactose | Trehalose | Maltose Trisaccharides Raffinose | Melezitose | Maltotriose Tetrasaccharides Acarbose | Stachyose Other oligosaccharides Fructooligosaccharide FOS | Galacto-oligosaccharide GOS | Mannan-oligosaccharides MOS Polysaccharide Glycogen | Starch Amylose | Amylopectin | Cellulose | Chitin | Inulin | Dextrin | Glucan Beta-glucan Glycosaminoglycans Heparin | Chondroitin sulfate | Hyaluronan | Heparan sulfate | Dermatan sulfate | Keratan sulfate Aminoglycosides Kanamycin | Streptomycin | Tobramycin | Neomycin | Paromomycin | Apramycin | Gentamicin | Netilmicin | Amikacin Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Glucose Categories: Glycolysis | Chemical pathology | Monosaccharides | Aldohexoses | Nutrition | SweetenersHidden categories: All articles with statements | Articles with statements since March 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Afrikaans العربية БеларуÑ?каÑ? БеларуÑ?каÑ? тарашкевіца Bosanski БългарÑ?ки Català Česky Dansk Deutsch Eesti Ελληνικά Español Esperanto Euskara Français Galego í•œêµì–´ हिनà¥?दी Hrvatski Bahasa Indonesia Ã?slenska Italiano עברית Kapampangan ქáƒ?რთული Latina LatvieÅ¡u Lietuvių Magyar МакедонÑ?ки Bahasa Melayu Nederlands 日本語 ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Occitan Oromoo Polski Português Română РуÑ?Ñ?кий Shqip Simple English SlovenÄ?ina SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Basa Sunda Suomi Svenska తెలà±?à°—à±? ไทย Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 20 August 2008, at 01:57
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