Glucose

This article is about the naturally-occuring D-form of glucose. For the L-form, see L-Glucose.

D-Glucose IUPAC name D-Glucose Other names Dextrose Identifiers Abbreviations Glc CAS number [50-99-7] EC number 200-075-1 ChemSpider 5589 PubChem 5793 SMILES   OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)1 (glucopyranose) ; OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O (acyclic glucose). Properties Chemical formula C6H12O6 Molar mass 180.16 g/mol Density 1.54 g/cm3 Melting point 146 °C Solubility in water 91 g/100 ml (25 °C) Solubility in methanol 0.037 M Solubility in ethanol 0.006 M Solubility in tetrahydrofuran 0.016 M Thermochemistry Std enthalpy of formation ΔfHo298 −1271 kJ/mol Std enthalpy of combustion ΔcHo298 −2805 kJ/mol Standard molar entropy So298 209.2 J K−1 mol−1 Hazards Material safety data sheet (MSDS) ICSC 0865 EU index number not listed Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

α-D-Glucopyranose IUPAC name α-D-Glucopyranose Identifiers InChI InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4​+,5-,6+/m1/s1 InChIKey WQZGKKKJIJFFOK-DVKNGEFBBQ Standard InChI InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4​+,5-,6+/m1/s1 Standard InChIKey WQZGKKKJIJFFOK-DVKNGEFBSA-N CAS number [492-62-6] EC number 207-757-8 ChemSpider 71358 Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

β-D-Glucopyranose IUPAC name β-D-Glucopyranose Identifiers InChI InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4​+,5-,6-/m1/s1 InChIKey WQZGKKKJIJFFOK-VFUOTHLCBI Standard InChI InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4​+,5-,6-/m1/s1 Standard InChIKey WQZGKKKJIJFFOK-VFUOTHLCSA-N CAS number [492-61-5] EC number 207-756-2 ChemSpider 58238 Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Glucose (Glc), a monosaccharide (or simple sugar) also known as grape sugar, blood sugar, or corn sugar, is a very 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 (bacteria and archaea) and eukaryotes (animals, plants, fungi, and protists).

The name "glucose" comes from the Greek word glukus (γλυκύς), meaning "sweet", and 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 glucose). 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.

Structure

Glucose (C₆H₁₂O₆) contains six carbon atoms, one of which is part of an aldehyde group. Therefore glucose is 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 (like 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 four chiral centers, giving 2⁴ = 16 stereoisomers. These are split into two groups, L and D, with eight sugars in each. Glucose is one of these sugars, and L-glucose and D-glucose are two of the stereoisomers. Only seven 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 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 chain 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 that it is cis. An inaccurate but superficially attractive alternative method of distinguishing α from β is observing whether the C-1 hydroxyl is below or above the plane of the ring; this 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. The ratio would be α:β 11:89 if it were not for the influence of the anomeric effect.

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  The Fischer projection of the chain form of D-glucose
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  The chain form of D-glucose
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  α-D-
  glucopyranose
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  β-D-
  glucopyranose
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  Chain form: ball-and-stick model
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  Chain form: space-filling model
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  α-D-
  glucopyranose
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  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. In 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. 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

Production

Natural

1. Glucose is one of the products of photosynthesis in plants and some prokaryotes.
2. 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.
3. 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.
4. In some deep-sea bacteria glucose is produced by chemosynthesis.

Commercial

Glucose is produced commercially via the enzymatic hydrolysis of starch. Many crops can be used as the source of starch. Maize, rice, wheat, cassava, corn husk and sago are all used in various parts of the world. In the United States, cornstarch (from maize) is used almost exclusively.

• Glucose 1.jpg

  Glucose

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  Glucose tablets

Function

Glucose metabolism and various forms of it in the process.
-Glucose-containing compounds and isomeric forms are digested and taken up by the body in the intestines, including starch, glycogen, disaccharides and monosaccharides.
-Glucose is stored in mainly the liver and muscles as glycogen.
-It is distributed and utilized in tissues as free glucose.

Scientists can speculate on the reasons why glucose, and not another monosaccharide such as fructose (Fru), is so widely used in organisms. One reason might be that glucose has a lower tendency, as compared 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, renal 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 a 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 respiration, anaerobic respiration, or 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. 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 sources, 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.

Glucose in glycolysis

Template:Enzymatic Reaction

Template:KEGG compound Template:KEGG enzyme Template:KEGG compound Template:KEGG reaction

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. In plants and most animals, it is also 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.

Industrial use

In the industry glucose is used as a precursor to make vitamin C in the Reichstein process, to make citric acid, gluconic acid, bio-ethanol, polylactic acid, sorbitol.

Sources and absorption

Most 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. Crystalline fructose, for example, does not contain glucose and is about ninety-eight percent fructose. In the lumen of the duodenum and small intestine, the glucose oligo- and polysaccharides are broken down to monosaccharides by the pancreatic and intestinal glycosidases. Other polysaccarhides cannot be processed by the human intestine and require assistance by intestinal flora if they are to be broken down; the most notable exceptions are sucrose (fructose-glucose) and lactose (galactose-glucose). Glucose is then transported across the apical membrane of the enterocytes by SLC5A1, and later across their basal membrane by SLC2A2. Some of the glucose is directly utilized as an energy source by brain cells, intestinal cells and red blood cells, 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 fat cells, 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.

History

Because 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 as a result of 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 isomers, applying van't Hoff's theory of asymmetrical carbon atoms.

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
• Sugars in wine
• Trinder glucose activity test
• Glucose transporter (GLUT): GLUT1, GLUT2

External links

• International Chemical Safety Card 0865
• Computational Chemistry Wiki
• What is Glucose