Putrescine

related topics
{acid, form, water}
{disease, patient, cell}
{film, series, show}
{company, market, business}

27 °C

158–160 °C

Putrescine (sometimes spelled putrescin) is a foul-smelling [1] organic chemical compound NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine) that is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses.[2][3] The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.

Contents

History

Putrescine[4] and cadaverine[5] were first described in 1885 by the Berlin physician Ludwig Brieger (1849-1919)[6].

Production

Putrescine is produced on industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile.[7] Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl.[8]

Biotechnological production of putrescine from renewable feedstock is a promising alternative to the chemical synthesis. A metabolically engineered strain of Escherichia coli that produces putrescine at high titer in glucose mineral salts medium has recently been described. [9]

Biochemistry

Putrescine attacks decarboxylated s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another decarboxylated s-adenosyl methionine and converts it to spermine.

Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.

Full article ▸

related documents
Vitamin E
Ketene
Hypoxanthine
List of synthetic polymers
Johannes Nicolaus Brønsted
Surfactant
Calamine (mineral)
Potassium ferrocyanide
Thermal diffusivity
Genetic material
Ununennium
Ornithine
Biocompatible material
Octahedrite
Uraninite
Anatase
Katharometer
Perlite
Carbon group
Isoleucine
Noncoding DNA
Phenyl group
Boron group
In vitro
Allene
Periodic table (standard)
Chymosin
Physical chemistry
Coenzyme A
Cobalt bomb