Putrescine
Encyclopedia
Putrescine is a foul-smelling organic chemical compound N
H
2(C
H2)4NH2 (1,4-diaminobutane or butanediamine) that is related to cadaverine
; both are produced by the breakdown of amino acid
s in living and dead organisms and both are toxic in large doses. 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
.
were first described in 1885 by the Berlin
physician Ludwig Brieger (1849–1919).
of succinonitrile
, which is produced by addition of hydrogen cyanide to acrylonitrile
. Putrescine is reacted with adipic acid
to yield the polyamide
Nylon
-4,6, which is marketed by DSM
under the trade name Stanyl.
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.
and gets converted to spermidine
. Spermidine in turn attacks another decarboxylated S-adenosyl methionine
and gets converted to spermine
.
Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase
. The polyamine
s, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.
of 2000 mg/kg body weight.
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
H
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
2(C
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
H2)4NH2 (1,4-diaminobutane or butanediamine) that is related to cadaverine
Cadaverine
Cadaverine is a foul-smelling compound produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH25NH2, which is similar to putrescine...
; both are produced by the breakdown of amino acid
Amino acid
Amino acids are molecules containing an amine group, a carboxylic acid group and a side-chain that varies between different amino acids. The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen...
s in living and dead organisms and both are toxic in large doses. The two compounds are largely responsible for the foul odor of putrefying
Putrefaction
Putrefaction is one of seven stages in the decomposition of the body of a dead animal. It can be viewed, in broad terms, as the decomposition of proteins, in a process that results in the eventual breakdown of cohesion between tissues and the liquefaction of most organs.-Description:In terms of...
flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen
Semen
Semen is an organic fluid, also known as seminal fluid, that may contain spermatozoa. It is secreted by the gonads and other sexual organs of male or hermaphroditic animals and can fertilize female ova...
and some microalgae, together with related molecules like spermine
Spermine
Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH...
and spermidine
Spermidine
Spermidine is a polyamine involved in cellular metabolism. Its known actions include:#Inhibition of neuronal nitric oxide synthase, nNOS#Assisting the in vitro process of transcribing RNA via stimulation of T4 polynucleotide kinase and T7 RNA polymerase activity; it binds to and precipitates DNA...
.
History
Putrescine and cadaverineCadaverine
Cadaverine is a foul-smelling compound produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH25NH2, which is similar to putrescine...
were first described in 1885 by the Berlin
Berlin
Berlin is the capital city of Germany and is one of the 16 states of Germany. With a population of 3.45 million people, Berlin is Germany's largest city. It is the second most populous city proper and the seventh most populous urban area in the European Union...
physician Ludwig Brieger (1849–1919).
Production
Putrescine is produced on industrial scale by hydrogenationHydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
of succinonitrile
Succinonitrile
Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H42. It is a colorless solid that melts at 57 °C, hence its waxy consistency.Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile:...
, which is produced by addition of hydrogen cyanide to acrylonitrile
Acrylonitrile
Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...
. Putrescine is reacted with adipic acid
Adipic acid
Adipic acid is the organic compound with the formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon...
to yield the polyamide
Polyamide
A polyamide is a polymer containing monomers of amides joined by peptide bonds. They can occur both naturally and artificially, examples being proteins, such as wool and silk, and can be made artificially through step-growth polymerization or solid-phase synthesis, examples being nylons, aramids,...
Nylon
Nylon
Nylon is a generic designation for a family of synthetic polymers known generically as polyamides, first produced on February 28, 1935, by Wallace Carothers at DuPont's research facility at the DuPont Experimental Station...
-4,6, which is marketed by DSM
DSM (company)
DSM is a multinational life sciences and materials sciences-based company. DSM's global end markets include food and dietary supplements, personal care, feed, pharmaceuticals, medical devices, automotive, paints, electrical and electronics, life protection, alternative energy and bio-based materials...
under the trade name Stanyl.
Biotechnological production of putrescine from renewable feedstock is a promising alternative to the chemical synthesis. A metabolically engineered strain of Escherichia coli
Escherichia coli
Escherichia coli is a Gram-negative, rod-shaped bacterium that is commonly found in the lower intestine of warm-blooded organisms . Most E. coli strains are harmless, but some serotypes can cause serious food poisoning in humans, and are occasionally responsible for product recalls...
that produces putrescine at high titer in glucose mineral salts medium has recently been described.
Biochemistry
Putrescine attacks decarboxylated S-adenosyl methionineS-Adenosyl methionine
S-Adenosyl methionine is a common cosubstrate involved in methyl group transfers. SAM was first discovered in Italy by G. L. Cantoni in 1952. It is made from adenosine triphosphate and methionine by methionine adenosyltransferase . Transmethylation, transsulfuration, and aminopropylation are the...
and gets converted to spermidine
Spermidine
Spermidine is a polyamine involved in cellular metabolism. Its known actions include:#Inhibition of neuronal nitric oxide synthase, nNOS#Assisting the in vitro process of transcribing RNA via stimulation of T4 polynucleotide kinase and T7 RNA polymerase activity; it binds to and precipitates DNA...
. Spermidine in turn attacks another decarboxylated S-adenosyl methionine
S-Adenosyl methionine
S-Adenosyl methionine is a common cosubstrate involved in methyl group transfers. SAM was first discovered in Italy by G. L. Cantoni in 1952. It is made from adenosine triphosphate and methionine by methionine adenosyltransferase . Transmethylation, transsulfuration, and aminopropylation are the...
and gets converted to spermine
Spermine
Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH...
.
Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase
Ornithine decarboxylase
The enzyme ornithine decarboxylase catalyzes the decarboxylation of ornithine to form putrescine. This reaction is the committed step in polyamine synthesis. In humans, this protein has 461 amino acids and forms a homodimer....
. The polyamine
Polyamine
A polyamine is an organic compound having two or more primary amino groups .This class of compounds includes several synthetic substances that are important feedstocks for the chemical industry, such as ethylene diamine , 1,3-diaminopropane , and hexamethylenediamine...
s, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.
Toxicity
Putrescine is toxic in large doses. In rats it had a fairly low acute oral toxicityAcute toxicity
Acute toxicity describes the adverse effects of a substance that result either from a single exposure or from multiple exposures in a short space of time...
of 2000 mg/kg body weight.