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Putrescine

Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

Production
Putrescine is produced on an industrial scale by the hydrogenation of succinonitrile. Biotechnological production of putrescine from a renewable feedstock has been investigated. A metabolically engineered strain of Escherichia coli that produces putrescine at high concentrations in glucose mineral salts medium has been described.{{cite journal| title = Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine| doi = 10.1002/bit.22502 ==Biochemistry==
Biochemistry
Spermidine synthase uses putrescine and S-adenosylmethioninamine (decarboxylated S-adenosyl methionine) to produce spermidine. Spermidine in turn is combined with another S-adenosylmethioninamine and gets converted to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. Putrescine is synthesized biologically via two different pathways, both starting from arginine. • In one pathway, arginine is converted into agmatine. The conversion is catalyzed by the enzyme arginine decarboxylase (ADC). Agmatine is transformed into N-carbamoylputrescine by agmatine imino hydroxylase (AIH). Finally, N-carbamoylputrescine is hydrolyzed to give putrescine. • In the second pathway, arginine is converted into ornithine and then ornithine is converted into putrescine by ornithine decarboxylase (ODC). Putrescine, via metabolic intermediates including N-acetylputrescine, γ-aminobutyraldehyde (GABAL), N-acetyl-γ-aminobutyric acid (N-acetyl-GABAL), and N-acetyl-γ-aminobutyric acid (N-acetyl-GABA), biotransformations mediated by diamine oxidase (DAO), monoamine oxidase B (MAO-B), aminobutyraldehyde dehydrogenase (ABALDH), and other enzymes, can act as a minor biological precursor of γ-aminobutyric acid (GABA) in the brain and elsewhere. In 2021, it was discovered that MAO-B does not mediate dopamine catabolism in the rodent striatum but instead participates in striatal GABA synthesis and that synthesized GABA in turn inhibits dopaminergic neurons in this brain area. It has been found that MAO-B, via the putrescine pathway, importantly mediates GABA synthesis in astrocytes in various brain areas, including in the hippocampus, cerebellum, striatum, cerebral cortex, and substantia nigra pars compacta (SNpc). ==Occurrence==
Occurrence
Putrescine is found in all organisms. Plants Putrescine is widely found in plant tissues, The absence of putrescine in plants is associated with an increase in both parasite and fungal population in plants. Putrescine serves an important role in a multitude of ways, which include: a cation substitute, an osmolyte, or a transport protein. Piriformospora indica (P. indica) is one such fungus, found to promote putrescine production in Arabidopsis and common garden tomato plants. In a 2022 study it was shown that the presence of this fungus had a promotional effect on the growth of the root structure of plants. After gas chromatography testing, putrescine was found in higher amounts in these root structures. Plants that had been inoculated with P. indica had presented an excess of arginine decarboxylase. It is also found in semen and some microalgae, together with spermine and spermidine. == Uses ==
Uses
Putrescine reacts with adipic acid to yield the polyamide nylon 46, which is marketed by Envalior (formerly DSM) under the trade name Stanyl. Due to its role in putrification, putrescine has also been proposed as a biochemical marker for determining how long a corpse has been decomposing. Agriculture Applying polyamines such as putrescine (PUT) to a plant causes lowered ethylene production. When applied pre-harvest, it increases plant resistance to high temperatures and drought. When applied post-harvest (to the fruits), PUT delays the ripening process and extends the shelf life. It is known to be applicable to a wide variety of fruits, including but not limited to peach, plum, cherry, tomato, and pear. It is also applicable to other edible parts such as broccoli. PUT has an all-round effect: it delays the deterioration of appearance (weight [mainly water] loss, % of rotten fruits, firmness), taste (total soluble solids, titratable acidity, organic acid content), and nutrition (phenol content, antioxidant content). ==History==
History
Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919). ==Toxicity==
Toxicity
In rats, putrescine has a low acute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day). ==Further reading==
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