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Hydrolysis

Hydrolysis


Hydrolysis literally means reaction with water. It is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. One fragment of the parent molecule gains a hydrogen ion (H+) from the additional water molecule. The other group collects the remaining hydroxyl group (OH). To illustrate this process, some examples from real life and actual living systems are discussed here.

The most common hydrolysis occurs when a salt of a weak acid or weak base (or both) is dissolved in water. Water autoionizes into negative hydroxyl ions and hydrogen ions. The salt breaks down into positive and negative ions. For example, sodium acetate dissociates in water into sodium and acetate ions. Sodium ions react very little with hydroxyl ions whereas acetate ions combine with hydrogen ions to produce neutral acetic acid, and the net result is a relative excess of hydroxyl ions, causing a basic solution.

However, under normal conditions, only a few reactions between water and organic compounds occur. Generally, strong acids or bases must be added in order to achieve hydrolysis where water has no effect. The acid or base is considered a catalyst . They are meant to speed up the reaction, but are recovered at the end of it.

Acidbase-catalyzed hydrolyses are very common; one example is the hydrolysis of amides or esters . Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than dipoles such as water. In acid, the carbonyl group becomes protonated, and this leads to a much easier nucleophilic attack. The products for both hydrolyses are compounds with carboxylic acid groups.

Perhaps the oldest example of ester hydrolysis is the process called saponification. It is the hydrolysis of a triglyceride (fat) with an aqueous base such as sodium hydroxide (NaOH). During the process, glycerol, also commercially named glycerin, is formed, and the fatty acids react with the base, converting them to salts. These salts are called soaps, commonly used in households.

Moreover, hydrolysis is an important process in plants and animals, the most significant example being energy metabolism and storage. All living cells require a continual supply of energy for two main purposes: for the biosynthesis of small and macromolecules, and for the active transport of ions and molecules across cell membranes. The energy derived from the oxidation of nutrients is not used directly but, by means of a complex and long sequence of reactions, it is channeled into a special energy-storage molecule, adenosine triphosphate (ATP) .

The ATP molecule contains pyrophosphate linkages (bonds formed when two phosphate units are combined together) that release energy when needed. ATP can be hydrolyzed in two ways: the removal of terminal phosphate to form adenosine diphosphate (ADP) and inorganic phosphate, or the removal of a terminal diphosphate to yield adenosine monophosphate (AMP) and pyrophosphate. The latter is usually cleaved further to yield two phosphates. This results in biosynthesis reactions, which do not occur alone, that can be driven in the direction of synthesis when the phosphate bonds are hydrolyzed.

In addition, in living systems, most biochemical reactions, including ATP hydrolysis, take place during the catalysis of enzymes. The catalytic action of enzymes allows the hydrolysis of proteins, fats, oils, and carbohydrates. As an example, one may consider proteases, enzymes that aid digestion by hydrolyzing peptide bonds in proteins. They catalyze the hydrolysis of interior peptide bonds in peptide chains, as opposed to exopeptidases, another class of enzymes, that catalyze the hydrolysis of terminal peptide bonds, liberating one free amino acid at a time.

However, proteases do not catalyze the hydrolysis of all kinds of proteins. Their action is stereo-selective: Only proteins with a certain tertiary structure will be targeted. The reason is that some kind of orienting force is needed to place the amide group in the proper position for catalysis. The necessary contacts between an enzyme and its substrates (proteins) are created because the enzyme folds in such a way as to form a crevice into which the substrate fits; the crevice also contains the catalytic groups. Therefore, proteins that do not fit into the crevice will not be hydrolyzed. This specificity preserves the integrity of other proteins such as hormones, and therefore the biological system continues to function normally.

see also Enzymes; Tertiary Structure.

Joseph Bariyanga

Bibliography

Freifelder, David (1987). Molecular Biology, 2nd edition. Boston: Jones and Bartlett.

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hydrolysis

hydrolysis (hīdrŏl´ĬsĬs), chemical reaction of a compound with water, usually resulting in the formation of one or more new compounds. The most common hydrolysis occurs when a salt of a weak acid or weak base (or both) is dissolved in water. Water ionizes into negative hydroxyl ions (OH-) and positive hydrogen ions (H+), which become hydrated to form positive hydronium ions (H3O+). The salt also breaks up into positive and negative ions. For example, when sodium acetate is dissolved in water it readily dissociates into sodium and acetate ions. Because sodium hydroxide is a strong base, the sodium ions react only slightly with the hydroxyl ions already present in the water to form sodium hydroxide molecules. Acetic acid is a weak acid, so the acetate ions react readily with the hydrogen ions present in the water to form neutral acetic acid molecules. The net result of these reactions is a relative excess of hydroxyl ions, causing an alkaline solution. A chemical reaction has actually taken place between the water and the dissolved salt. There are relatively few instances in which water reacts directly with organic compounds under ordinary conditions. It does react with acid halides, acid anhydrides, and organometallic compounds, e.g., Grignard reagents. The addition of strong acids or bases or the use of steam will often bring about hydrolysis where ordinary water has no effect. Some industrially important hydrolysis reactions are the synthesis of alcohols from olefins (e.g., ethanol, CH3COOH, from ethene, CH2CH2) in the presence of a strong acid catalyst, the conversion of starches to sugars in the presence of a strong acid catalyst, and the conversion of animal fats or vegetable oils to glycerol and fatty acids by reaction with steam. Hydrolysis is an important reaction in plants and animals (see metabolism). The catalytic action of certain enzymes allows the hydrolysis of proteins, fats, oils, and carbohydrates.

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hydrolysis

hydrolysis
1. (biochem.) A reaction between a substance and water in which the substance is split into two or more products. At the points of cleavage the products react with the hydrogen or hydroxyl ions derived from water.

2. (pedol.) The process of enriching the soil adsorption complex with hydrogen after exchangeable metallic ions have been replaced by hydrogen ions. Compare weathering.

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hydrolysis

hydrolysis
1. (biochem.) A reaction between a substance and water in which the substance is split into 2 or more products. At the points of cleavage the products react with the hydrogen or hydroxyl ions derived from water.

2. (pedol.) The process of enriching the soil adsorption complex with hydrogen after exchangeable metallic ions have been replaced by hydrogen ions.

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hydrolysis

hydrolysis
1. Reaction between a substance and water in which the substance is split into two or more products. At the points of cleavage the products react with the hydrogen or hydroxyl ions derived from water.

2. Process of enriching the soil adsorption complex with hydrogen after exchangeable metallic ions have been replaced by hydrogen ions. Compare WEATHERING.

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hydrolysis

hydrolysis Chemical reaction in which molecules are split into smaller molecules by reaction with water; often assisted by a catalyst. For example, in digestion, enzymes catalyse the hydrolysis of carbohydrates, proteins, and fats into smaller, soluble molecules that the body can assimilate.

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hydrolysis

hy·drol·y·sis / hīˈdräləsis/ • n. Chem. the chemical breakdown of a compound due to reaction with water. DERIVATIVES: hy·dro·lyt·ic / ˌhīdrəˈlitik/ adj.

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hydrolysis

hydrolysis A reaction between a substance and water in which the substance is split into two or more products. At the points of cleavage the products react with the hydrogen or hydroxyl ions derived from water.

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hydrolysis

hydrolysis (hy-drol-i-sis) n. any chemical reaction in which a compound and water react together to produce other compounds.

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