300px, The s_of_glucose">Fischer_projections_of_glucose_and_glucuronic_acid.html" ;"title="glucose.html" ;"title="Fischer projections of glucose">Fischer projections of glucose and glucuronic acid">glucose.html" ;"title="Fischer projections of glucose">Fischer projections of glucose and glucuronic acid. Glucose's terminal carbon's primary alcohol group has been oxidized to a
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...
.
Uronic acids () or alduronic acids are a class of
sugar acid A Sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its chain.
Main classes of sugar acids include:
* Aldonic acids, in which the aldehyde group (−CHO) located at the initial end ( position 1) of an ...
s with both
carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
and
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the r ...
s. They are
sugar
Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or do ...
s in which the
hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydrox ...
group furthest from the carbonyl group has been oxidized to a
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...
. Usually the sugar is an
aldose
An aldose is a monosaccharide (a simple sugar) with a carbon backbone chain with a carbonyl group on the endmost carbon atom, making it an aldehyde, and hydroxyl groups connected to all the other carbon atoms. Aldoses can be distinguished from ...
, but
fructuronic acid also occurs. Oxidation of the terminal
aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl gro ...
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
hexose
In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.
Hexoses exist in two forms, open-chain or cyclic, that easily convert ...
s are known as hexuronic acids and uronic acids derived from
pentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.[glucuronate
Glucuronic acid (from Greek γλεῦκος "''wine, must''" and οὖρον "''urine''") is a uronic acid that was first isolated from urine (hence the name). It is found in many gums such as gum arabic (c. 18%), xanthan, and kombucha tea and i ...]
salts, and
iduronic acid
-Iduronic acid (IUPAC abbr.: IdoA) is the major uronic acid component of the glycosaminoglycans (GAGs) dermatan sulfate, and heparin. It is also present in heparan sulfate
Heparan sulfate (HS) is a linear polysaccharide found in all animal tiss ...
is a component of some structural complexes such as
proteoglycans
Proteoglycans are proteins that are heavily glycosylated. The basic proteoglycan unit consists of a "core protein" with one or more covalently attached glycosaminoglycan (GAG) chain(s). The point of attachment is a serine (Ser) residue to which ...
.
See also
*
Gluconic acid
Gluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4COOH. It is one of the 16 stereoisomers of 2,3,4,5,6-pentahydroxyhexanoic acid.
In aqueous solution at neutral pH, gluconic acid ...
*
Glucuronic acid
Glucuronic acid (from Greek γλεῦκος "''wine, must''" and οὖρον "''urine''") is a uronic acid that was first isolated from urine (hence the name). It is found in many gums such as gum arabic (c. 18%), xanthan, and kombucha tea ...
*
Isosaccharinic acid
Isosaccharinic acid (ISA) is a six-carbon sugar acid which is formed by the action of calcium hydroxide on lactose and other carbohydrates. It is of interest because it may form in intermediate-level nuclear waste stores when cellulose is degra ...
References
External links
* {{MeshName, Uronic+Acids
Synthesis at chembio.uoguelph.ca
Sugar acids
Vicinal diols