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Pimelic acid
 
 
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Pimelic acid is the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2C(CH2)5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 called lysine
Lysine

Lysine is an a-amino acid with the chemical formula HO2CCH4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it....
. Pimelic acid is one methylene longer than a related dicarboxylic acid
Dicarboxylic acid

Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkane, alkene, or alkyne group....
, adipic acid, a precursor to many polyesters and polyamides. It is the final member of the mnemonic used to aid recollection of the order of the first six dicarboxylic acids using their common (not IUPAC) nomenclature:

Pimelic acid has been synthesized from cyclohexanone
Cyclohexanone

Cyclohexanone is the organic compound with the chemical formula...
 and from salicylic acid
Salicylic acid

Salicylic acid is a beta hydroxy acid with the chemical formula C6H4COOH, where the OH group is adjacent to the carboxylic acid....
.






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Pimelic acid is the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2C(CH2)5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 called lysine
Lysine

Lysine is an a-amino acid with the chemical formula HO2CCH4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it....
. Pimelic acid is one methylene longer than a related dicarboxylic acid
Dicarboxylic acid

Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkane, alkene, or alkyne group....
, adipic acid, a precursor to many polyesters and polyamides. It is the final member of the mnemonic used to aid recollection of the order of the first six dicarboxylic acids using their common (not IUPAC) nomenclature:

Pimelic acid has been synthesized from cyclohexanone
Cyclohexanone

Cyclohexanone is the organic compound with the chemical formula...
 and from salicylic acid
Salicylic acid

Salicylic acid is a beta hydroxy acid with the chemical formula C6H4COOH, where the OH group is adjacent to the carboxylic acid....
. In the former route, the additional carbon is suppled by dimethyloxalate
Oxalate

An oxalate is the deprotonated, charged form of oxalic acid or an ester of oxalic acid. As a salt, the oxalate anion has the chemical formula C2O42- or 22-....
, which reacts with the enolate.

See also

  • Diaminopimelic acid
    Diaminopimelic acid

    Diaminopimelic acid is an amino acid derivative. It is closely related to lysine.It is a characteristic of certain cell walls and is the attachment point for Braun's lipoprotein....