Glucose

From Wikipedia, the free encyclopedia.

Glucose (Glc), a simple monosaccharide sugar, is one of the most important carbohydrates and is used as a source of energy in animals and plants. Glc is one of the main products of photosynthesis and starts respiration. The natural form (D-glucose) is also referred to as dextrose, especially in the food industry.

Contents 1 Structure 1.1 Isomers 2 Synthesis 2.1 Natural 2.2 Commercial 3 Function 3.1 As an energy source 3.2 As a precursor 4 Sources and absorbtion 5 See also 6 External links

Structure

Glc, is a hexose—a monosaccharide containing six carbon atoms. Glc is an aldehyde (contains a -CHO group). Five of the carbons plus an oxygen atom form a loop called a "pyranose ring", the most stable form for six-carbon aldoses. In this ring, each carbon is linked to hydroxyl and hydrogen side groups with the exception of the fifth atom, which links to a 6th carbon atom outside the ring, forming a CH₂OH group. This ring structure exists in equilibrium with a more reactive acyclic form, which makes up 0.0026% at pH 7.

Isomers

There are two enantiomers (mirror-image isomers) of Glc, D-Glc and L-Glc, but in living organisms, only the D-isomer is found. Whether a carbohydrate is D or L has to do with the isomeric conformation of the hydroxyl at the C atom that is second to the last one, which in the case of Glc is C atom 5, the position reflects a relation to the D- or L- form of the "parent" for all sugars glyceraldehyd. If it is to the right in the Fischer projection, then the ring form will be the D enantiomer, if it is to the left, it will be the L enantiomer. This is easy to remember, as the D is for "dextro," which is a Latin root for "right," where as L is for "levo" which comes from the Latin root for "left." The ring structure itself may form in two additionally different ways, yielding α-Glc and β-Glc. Structurally, they differ in the orientation of the hydroxyl group linked to the first carbon in the ring. The α form has the hydroxyl group "below" the hydrogen (as the molecule is conventionally drawn, as in the figure in the table above), while the β form has the hydroxyl group "above" the hydrogen.

These two 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. This process can be speeded up.

Synthesis

Natural

1. The product of photosynthesis in plants and some prokaryotes.
2. Formed in the liver and skeletal muscle by the breakdown of glycogen stores (Glc polymers).
3. Synthesized in liver and kidneys from intermediates by a process known as gluconeogenesis.

Commercial

Glc is prepared commercially via the enzymatic hydrolysis of starch. Many crops can be used as the source of the initial 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 two stages. Over the course of 1–2 hours near 100 °C, these enzymes hydrolyze starch into smaller carbohydrates containing on average 5–10 Glc units each. Some variations on this process briefly heat the starch mixture to 130 °C or hotter one or more times. This heat treatment improves the solubility of starch in water, but deactivates the enzyme, and fresh enzyme must be added to the mixture after each heating.

In the second step, saccharification, the partially hydrolyzed starch is completely hydrolyzed to Glc 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 Glc at 96% yield after 1–4 days. Still higher 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. The resulting glucose solution is then purified by filtration and concentrated in a multiple-effect evaporator. Solid D-Glc is then produced by repeated crystallizations.

Function

We can speculate on the reasons why Glc, and not another monosaccharide such as Fru, is so widely used. Glc can form from 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 Glc, by comparison to other hexose sugars, to nonspecifically react with the amino groups of proteins. This reaction (glycosylation) reduces or destroys the function of many enzymes. The low rate of glycosylation is due to Glc'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 glycosylation of proteins.

As an energy source

Glc is a ubiquitous fuel in biology. Carbohydrates are the human body's key source of energy, providing 4 calories (17 kilojoules) of food energy per gram. Breakdown of carbohydrates (e.g. starch) yields mono- and disaccharides, most of which is Glc. Through glycolysis and later in the reactions of TCAC, Glc is oxidized to eventually form CO₂ and water, yielding energy, mostly in the form of ATP.

As a precursor

Glc is critical in the production of protein and in lipid metabolism. As the CNS does not metabolise lipids, it is more dependent on Glc than other tissues.

Glc is used as a precursor for the synthesis of several important substances. Starch, cellulose, and glycogen ("animal starch") are common Glc polymers (polysaccharides). Lactose - the milk sugar, is a Glc-Gal disaharde. In Sucrose, another important disaccharyde, Glc is joined to Fru.

Sources and absorbtion

Glucose is absorbed into the bloodstream through the intestinal wall. Only the mono-saccharides Glc, Fru and Gal are absorbed in humans; these are the end-products of the digestion of carbohydrates. Glc and Gal are absorbed via a Na⁺-dependent transporter protein into the intestinal cell (GLUT2). Some of this Glc goes directly to fuel brain cells, while the rest makes its way to the liver and muscles, where it is stored as glycogen, and to fat cells, where it is stored as fat. Glycogen is the body's auxiliary energy source, tapped and converted back into Glc when it needs more energy. Although stored fat can also serve as a backup source of energy, it is never directly converted into Glc. Most of the dietary Fru is converted to Glc in the enterocytes, the rest of it and Gal are taken up by the liver, where they are converted into Glc.

See also

• HbA1c

External links

• More on the chemistry and function of glucose in biology at EvoWiki
• Computational Chemistry Wiki