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Putrescine: structure, properties, synthesis, uses

Putrescine, along with cadaverine, are responsible for the bad smell of rotting meat, bad breath and bacterial vaginosis. Hence its name. Both diamines were characterized for the first time by the German physician Ludwig Brieger, in 1885.

Putrescine is directly involved in the synthesis of spermedine, another polyamine, by reacting with S-adenosylmethionine. Also, spermedine reacts with S-adenosylmethionine to generate polyamine spermine.

There is evidence that polyamines, including putrescine, are growth factors necessary for cell division. A constant supply of polyamines is a prerequisite for cell proliferation to occur.

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Structure of putrescine

Putrescine molecule represented by a model of spheres and bars. Source: Karlhahn / Public domain

The top image shows the molecular structure of putrescine. Being its structure so simple, it is ironic that we are able to recognize it by its bad smell. The gray spheres make up its carbon skeleton of n- butane, while the blue ones correspond to the nitrogen atoms of the NH 2 groups .

These NH 2 groups can be protonated, which will cause the putrescine molecule to acquire two positive charges, H 3 N + CH 2 CH 2 CH 2 CH 2 NH + . Therefore, he becomes a polycation.

Putrescine is a polar molecule, whose intermolecular interactions are based on the dipole-dipole forces, and on the London dispersive forces. This is the reason why it is a solid amine at room temperature, and has a high boiling point compared to other amines.

Properties of putrescine

Molecular formula

4 H 12 N 2

Molecular weight

88.15 g / mol

Appearance

Colorless crystals that melt into a colorless oil.

Odor

Strong, similar to piperidine.

Density

0.877 g / mL

Melting point

27.5 ºC

Boiling point

158.6 ºC

Octanol / water partition coefficient

Log P = – 0.7

Vapor pressure

2.33 mmHg at 25 ºC

Refractive index (nD)

1,455

Water solubility

Very soluble.

pKa

10.8 to 20 ºC

Decomposition

When heated to decomposition, putrescine emits toxic nitrogen oxide gases.

Stability

Incompatible with strong oxidizing agents.

Reactivity

In aqueous solution, it has a strong basic behavior due to its two amino groups. Putrescine reacts with S-adenosylmethionine to form polyamine spermidine, and indirectly putrescine originates polyamine spermine.

Putrescine is produced industrially by the hydrogenation of the chemical compound succinonitrile, which in turn is produced by the reaction of hydrogen cyanide with acrylonitrile.

Putrescine, through the use of biotechnology, is being synthesized in culture media of certain strains of the bacterium E. coli.

Gram negative bacteria can synthesize putrescine in three ways:

-Ornithine is generated from the amino acid arginine. Then, ornithine, by the action of the enzyme ornithine decarboxylase, synthesizes putrescine

-Arginine synthesizes agmantine by the action of arginine decarboxylase. Subsequently, amantine originates putrescine

-In a third way, agmatine is directly transformed into putrescine and urea by the action of the enzyme agmatinase.

Gram positive bacteria use other pathways for the synthesis of putrescine.

Putrescine uses

Industrial

The American company Dupont initially marketed nylon 6.6. This was characterized by a 6-carbon diamine and a 6-carbon diacid (adipic acid), which were interspersed in the polymer structure. In 1990, the Dutch company introduced nylon 4.6 to the market.

Nylon 4.6 was marketed under the name Stanyl, which uses putrescine consisting of 4 carbon atoms as a diamine, thus maintaining the use of the same diacid as in nylon 6.6.

Stanyl is used in engine chain guides and gear trains, exhibiting good resistance to wear and friction action, especially at high temperatures.

Drug production 

Putrescine decarboxylation is the initial step in a sequence of biochemical events that lead to the synthesis of scopolamine: a highly toxic drug whose high doses can cause death. Scopolamine (burrundanga) is frequently used in criminal actions.

Scopolamine is used in very low doses in the treatment of vehicular dizziness, nausea, vomiting and colitis.

The enzyme putrescine-N-methyltransferase (PMT) acts on putrescine in a biochemical process mediated by S-adenosylmethionine that leads to the synthesis of nicotine, tropane, and a nortropane alkaloid.

Nicotine is a toxic drug that is used as an agricultural insecticide, while in veterinary medicine it is used as an external antiparasitic.

Biological action

Biosynthesis of spermidine and spermine from putrescine. Ado = 5′-adenosyl. Source: Andrew Murkin / CC BY-SA (https://creativecommons.org/licenses/by-sa/4.0)

Putrescine, like other polyamines, such as cadaverine, spermedine and spermine, are polycationic molecules due to the presence of amino groups. Therefore, they can interact electrostatically with nucleic acids, phospholipids, and negatively charged proteins.

This interaction allows the action of polyamines in numerous biochemical events, such as:

-Regulation of DNA and protein synthesis

-Elimination of reactive oxygen species

-Activation of cell proliferation

-Tissue differentiation and development

Among the cellular functions in which polyamines intervene, are the maturation of the intestinal mucosa and cell migration. Putrescine plays a specific role in skin physiology and neuroprotection.

Although polyamines are attributed numerous biological functions, they have also been linked to the generation of cancer. The enzyme ornithine decarboxylase, an enzyme that catalyzes the conversion of ornithine to putrescine, is present in several human and rodent cancers.

An increase in the concentration of polyamines is directly related to a set of cellular processes related to tumor invasion and metastasis. Furthermore, it is noted that putrescine may be a precursor to N-nitrosamine, a carcinogenic agent.

Toxicity

Putrescine itself has a low toxicity, but it is capable of acting by enhancing the toxic effect of histamine that is generated in the decomposition of meat, as well as that of tyramine generated in cheese.

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