This article relies largely or entirely on a single source .(July 2024) |
Names | |
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IUPAC name β-D-Galactopyranuronic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.035.495 |
EC Number |
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PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C6H10O7 | |
Molar mass | 194.139 |
Melting point | 159 °C (318 °F; 432 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
d-Galacturonic acid is a sugar acid, an oxidized form of d-galactose. It is the main component of pectin, in which it exists as the polymer polygalacturonic acid. [1] In its open form, it has an aldehyde group at C1 and a carboxylic acid group at C6. Other oxidized forms of d-galactose are d-galactonic acid (carboxylic group at C1) and meso-galactaric acid (mucic acid) (carboxylic groups at C1 and C6). It is also a uronic acid or hexuronic acid. Naturally occurring uronic acids are d-glucuronic acid, d-galacturonic acid, l-iduronic acid and d-mannuronic acid.
In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.
Pectin is a heteropolysaccharide, a structural polymer contained in the primary lamella, in the middle lamella, and in the cell walls of terrestrial plants. The principal chemical component of pectin is galacturonic acid which was isolated and described by Henri Braconnot in 1825. Commercially produced pectin is a white-to-light-brown powder, produced from citrus fruits for use as an edible gelling agent, especially in jams and jellies, dessert fillings, medications, and sweets; and as a food stabiliser in fruit juices and milk drinks, and as a source of dietary fiber.
A reducing sugar is any sugar that is capable of acting as a reducing agent. In an alkaline solution, a reducing sugar forms some aldehyde or ketone, which allows it to act as a reducing agent, for example in Benedict's reagent. In such a reaction, the sugar becomes a carboxylic acid.
Glycosaminoglycans (GAGs) or mucopolysaccharides are long, linear polysaccharides consisting of repeating disaccharide units. The repeating two-sugar unit consists of a uronic sugar and an amino sugar, except in the case of the sulfated glycosaminoglycan keratan, where, in place of the uronic sugar there is a galactose unit. GAGs are found in vertebrates, invertebrates and bacteria. Because GAGs are highly polar molecules and attract water; the body uses them as lubricants or shock absorbers.
Aldaric acids are a group of sugar acids, where the terminal hydroxyl and carbonyl groups of the sugars have been replaced by terminal carboxylic acids, and are characterised by the formula HO2C-(CHOH)n-CO2H. Oxidation of just the aldehyde yields an aldonic acid while oxidation of just the terminal hydroxyl group yields an uronic acid.) Aldaric acids cannot form cyclic hemiacetals like unoxidized sugars, but they can sometimes form lactones.
Glucuronic acid is a uronic acid that was first isolated from urine. It is found in many gums such as gum arabic, xanthan, and kombucha tea and is important for the metabolism of microorganisms, plants and animals.
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.
In organic chemistry, a sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its chain.
Uronic acids or alduronic acids are a class of sugar acids with both carbonyl and carboxylic acid functional groups. They are sugars in which the hydroxyl group furthest from the carbonyl group has been oxidized to a carboxylic acid. Usually the sugar is an aldose, but fructuronic acid also occurs. Oxidation of the terminal aldehyde instead yields an aldonic acid, while oxidation of both the terminal hydroxyl group and the aldehyde yields an aldaric acid. The names of uronic acids are generally based on their parent sugars, for example, the uronic acid analog of glucose is glucuronic acid. Uronic acids derived from hexoses are known as hexuronic acids and uronic acids derived from pentoses are known as penturonic acids.
Aldonic acids are sugar acids with the general chemical formula, HO2C(CHOH)nCH2OH. They are obtained by oxidizing the aldehyde (-CHO group) of an aldose to form a carboxylic acid (-COOH group). Aldonic acids are generally found in their ring form. However, these rings do not have a chiral carbon at the terminal end bearing the aldehyde, and they cannot form R−O−R′ linkages between different molecules.
Wall-associated kinases (WAKs) are one of many classes of plant proteins known to serve as a medium between the extracellular matrix (ECM) and cytoplasm of cell walls. They are serine-threonine kinases that contain epidermal growth factor (EGF) repeats, a cytoplasmic kinase and are located in the cell walls. They provide a linkage between the inner and outer surroundings of cell walls. WAKs are under a group of receptor-like kinases (RLK) that are actively involved in sensory and signal transduction pathways especially in response to foreign attacks by pathogens and in cell development. On the other hand, pectins are an abundant group of complex carbohydrates present in the primary cell wall that play roles in cell growth and development, protection, plant structure and water holding capacity.
In enzymology, a fructuronate reductase (EC 1.1.1.57) is an enzyme that catalyzes the chemical reaction
In enzymology, a glucuronate isomerase is an enzyme that catalyzes the chemical reaction
Rhamnogalacturonan-II (RG-II) is a complex polysaccharide component of pectin that is found in the primary cell walls of dicotyledonous and monocotyledonous plants and gymnosperms. It is supposed to be crucial for the plant cell wall integrity. RG-II is also likely to be present in the walls of some lower plants. Its global structure is conserved across vascular plants, albeit a number of variations within the RGII side chains have been observed between different plants. RG-II is composed of 12 different glycosyl residues including D-rhamnose, D-apiose, D-galactose, L-galactose, Kdo, D-galacturonic acid, L-arabinose, D-xylose, and L-aceric acid, linked together by at least 21 distinct glycosidic linkages. Some resides are further modified via methylation and acetylation. It moreover supports borate mediated cross-linking between different RGII side-chain apiosyl residues. The backbone consists of a linear polymer of alpha-1,4-linked D-galactopyranosiduronic acid. RG-II can be isolated from different sources, such as apple juice and red wine.
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters where the carbon carries a higher oxidation state. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids.
The Pinnick oxidation is an organic reaction by which aldehydes can be oxidized into their corresponding carboxylic acids using sodium chlorite (NaClO2) under mild acidic conditions. It was originally developed by Lindgren and Nilsson. The typical reaction conditions used today were developed by G. A. Kraus. H.W. Pinnick later demonstrated that these conditions could be applied to oxidize α,β-unsaturated aldehydes. There exist many different reactions to oxidize aldehydes, but only a few are amenable to a broad range of functional groups. The Pinnick oxidation has proven to be both tolerant of sensitive functionalities and capable of reacting with sterically hindered groups. This reaction is especially useful for oxidizing α,β-unsaturated aldehydes, and another one of its advantages is its relatively low cost.
Aromatic acids are a type of aromatic compound. Included in that class are substances containing an aromatic ring and an organic acid functional group. There are several categories of aromatic acids including:
Galactose oxidase is an enzyme that catalyzes the oxidation of D-galactose in some species of fungi.
In organic chemistry, a benzylidene acetal is the functional group with the structural formula C6H5CH(OR)2 (R = alkyl, aryl). Benzylidene acetals are used as protecting groups in glycochemistry. These compounds can also be oxidized to carboxylic acids in order to open important biological molecules, such as glycosaminoglycans, to other routes of synthesis. They arise from the reaction of a 1,2- or 1,3-diols with benzaldehyde. Other aromatic aldehydes are also used.
Guluronic acid is a uronic acid monosaccharide that may be derived from gulose. l-Guluronic acid is a C-3 epimer of l-galacturonic acid and a C-5 epimer of d-mannuronic acid. Along with d-mannuronic acid, l-guluronic acid is a component of alginic acid, a polysaccharide found in brown algae. α-L-Guluronic acid has been found to bind divalent metal ions through the carboxylate moiety and through the axial-equatorial-axial arrangement of hydroxyl groups found around the ring.