Carboxyl in the context of Omega hydroxy acid


Carboxyl in the context of Omega hydroxy acid

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⭐ Core Definition: Carboxyl

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

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👉 Carboxyl in the context of Omega hydroxy acid

Omega hydroxy acids (ω-hydroxy acids) are a class of naturally occurring straight-chain aliphatic organic acids n carbon atoms long with a carboxyl group at position 1 (the starting point for the family of carboxylic acids), and a hydroxyl at terminal position n where n > 3. They are a subclass of hydroxycarboxylic acids. The C16 and C18 omega hydroxy acids 16-hydroxy palmitic acid and 18-hydroxy stearic acid are key monomers of cutin in the plant cuticle. The polymer cutin is formed by interesterification of omega hydroxy acids and derivatives of them that are substituted in mid-chain, such as 10,16-dihydroxy palmitic acid. Only the epidermal cells of plants synthesize cutin.

Omega hydroxy fatty acids also occur in animals. Cytochrome P450 (CYP450) microsome ω-hydroxylases such as CYP4A11, CYP4A22, CYP4F2, and CYP4F3 in humans, Cyp4a10 and Cyp4a12 in mice, and Cyp4a1, Cyp4a2, Cyp4a3, and Cyp4a8 in rats metabolize arachidonic acid and many arachidonic acid metabolites to their corresponding omega hydroxyl products. This metabolism of arachidonic acid produces 20-hydroxyarachidonic acid (i.e. 20-hydroxyeicosatetraeonic acid or 20-HETE), a bioactive product involved in various physiological and pathological processes; and this metabolism of certain bioactive arachidonic acid metabolites such as leukotriene B4 and 5-hydroxyicosatetraenoic acid produces 20-hydroxylated products which are 100- to 1,000-fold weaker than, and therefore represents the inactivation of, their respective precursors.

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Carboxyl in the context of Tannin

Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term tannin is widely applied to any large polyphenolic compound containing sufficient hydroxyls and other suitable groups (such as carboxyls) to form strong complexes with various macromolecules.

The term tannin (from scientific French tannin, from French tan "crushed oak bark", tanner "to tan", cognate with English tanning, Medieval Latin tannare, from Proto-Celtic *tannos "oak") refers to the abundance of these compounds in oak bark, which was used in tanning animal hides into leather.

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Carboxyl in the context of Lactic acid

Lactic acid is an organic acid with the molecular formula C3H6O3. In its solid state, it is white and miscible with water. When dissolved, it forms a colorless solution. Production includes both artificial synthesis and natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate (or the lactate anion). The name of the derived acyl group is lactoyl.

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Carboxyl in the context of Carbamic acid

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4][NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

Carbamic acid could be seen as both an amine and carboxylic acid, and therefore an amino acid; however, the attachment of the carboxyl group –COOH directly to the nitrogen atom (without any intermediate carbon chain) makes it behave very differently from the amino acids with intermediate carbon chain. (Glycine NH2CH2COOH is generally considered to be the simplest amino acid.) The hydroxyl group –OH attached to the carbon also excludes it from the amide class.

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Carboxyl in the context of Protein secondary structure

Protein secondary structure is the local spatial conformation of the polypeptide backbone excluding the side chains. The two most common secondary structural elements are alpha helices and beta sheets, though beta turns and omega loops occur as well. Secondary structure elements typically spontaneously form as an intermediate before the protein folds into its three dimensional tertiary structure.

Secondary structure is formally defined by the pattern of hydrogen bonds between the amino hydrogen and carboxyl oxygen atoms in the peptide backbone. Secondary structure may alternatively be defined based on the regular pattern of backbone dihedral angles in a particular region of the Ramachandran plot regardless of whether it has the correct hydrogen bonds.

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Carboxyl in the context of Glutathione

Glutathione (GSH, /ˌɡltəˈθn/) is an organic compound made of the amino acids glutamate, cysteine, and glycine. It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, peroxides, lipid peroxides, and heavy metals. It is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and cysteine. The carboxyl group of the cysteine residue is attached by normal peptide linkage to glycine.

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