Diamines putrescine

Species of Pseudomonas can utilize the a,(i)-diamines putrescine, spermidine, and spermine as sources of carbon and nitrogen, and putrescine can be produced from the secondary amine spermidine together with 1,3-diaminopropane (Dasu et al. 2006). Putrescine (1,4-diaminobutane) is an intermediate in the arginine decarboxylase (ADC) pathway of L-arginine degradation, which is described later, and can be degraded, by two pathways ... 

Diamine oxidase, a soluble enzyme found in liver and other tissues, is mainly involved in the metabolism of endogenous compounds such as the aliphatic diamine putrescine (chap. 7, Fig. 40). 

Nicotine.—The pyrrolidine ring of nicotine (6) derives from ornithine (1), label from, e.g., C-2 appearing equally spread over C-2 and C-5. This symmetrical incorporation of the precursor amino-acid is accounted for by the intermediacy of the symmetrical diamine putrescine (4), which is supported by other evidence too.1,2 The symmetrical incorporation of ornithine into nicotine (6) and into nornicotine (7) has been confirmed by the results4 of experiments with [2,3-13C2]ornithine [as (1)], thus reinforcing earlier 14C and 13C results (cf. Vol. 8, p. 5 Vol. 10, p. 14). Equal labelling of C-2, C-3 and of C-4, C-5 was observed. 

Decarboxylation of ornithine 269a gives the diamine putrescine 275 (Scheme 74) which is used in the biosynthesis of many alkaloids. LrOrnithine decarboxylase (EC 4.1.1.17) catalyzes this reaction, and when unlabeled ornithine is decarboxylated in and [2- HJornithine is decarboxylated in HjO, samples of (IK)- and (lS)-[l- Hi]putrescine 275, Hb = and 275, Ha = H, respectively, are obtained (283). The configuration of these samples was assessed by conversion to [ HJ-Af-phthalimidobutyrate of known chirality (283) or by H NMR spectroscopic techniques (277,284). The enzyme has been used extensively to prepare stereospecifically labeled samples of putrescine 275 for biosynthetic studies (278, 285-290). 

Yamamoto et al. (1982) developed a quantitative method for the determination of putrescine, cadaverine, spermidine, and spermine in foods. Separation of the amines from foods was achieved by eluting through a cation-exchange resin column and then converted to their (ethyloxy) carbonyl derivatives by the reaction with ethyl chloroformate in aqueous medium before application to the gas chromatograph with a flame ionization detector. They used 1,8-diaminooctane as an internal standard and performed the separation and determination of the resulting derivatives on a 1.5% SE-30/0.3% SP-1000 on Uniport HP column (0.5 m) under the temperature-programmed condition. Staruszkiewicz and Bond (1981) developed a GLC procedure for the quantitative determination of the diamines putrescine... 

Further characterization of the TX4 cells showed that the main phenolic compounds were the caffeoyl-, feruloyl- and coumaroyl amides of the diamine putrescine (1,4-diaminobutane)... 

Another characteristic of mineral-deficient plants is the increase in nonprotein amino acids and other nitrogenous compounds which are usually present at very low concentrations or are not detectable. The most studied of these compounds is the diamine, putrescine. An accumulation of putrescine in the leaves of higher plants deficient in K was first observed in barley (Richards and Coleman, 1952) and it has subsequently been shown to accumulate in K-deficient plants of many species (Coleman and Richards, 1956 Smith, 1963, 1%9, 1970). Putrescine also accumulates under conditions of Mg deficiency (Smith, 1970, 1973 Basso and Smith, 1974), although the increase in barley (fourfold) was less than that (13-fold) in K-deficient plants. 

Mattoo, A.K. Minocha, S.C. Minocha, R. Handa, A.K. (2010). Polyamines and cellular metabolism in plants transgenic approaches reveal different responses to diamine putrescine versus higher polyamines spermidine and spermine. Amino Acids, Vol. 38, No. 2, pp 405-413, ISSN 0939-4451. 

Pyridoxal phosphate-catalyzed decarboxylation (ornithine decarboxylase, EC 4.1.1.17) yields butane-1,4-diamine (putrescine) directly. Arginine (Arg, R) first undergoes pyridoxal phosphate-catalyzed decarboxylation (arginine [Arg, R] decarboxylase, EC 4.1.1.19) to agmatine and then hydrolytic loss of urea (agmatinase, EC 3.5.3.11) to produce the same diamine. Ornithine and arginine (Arg, R) are members... 

Biogenic amines with more significant adverse effects on human health are histamine, tyramine and 2-phenylethylamine. The increased content of diamines putrescine and cadaverine serves primarily as an indicator of deficiencies in processing technology... 

G.K., and Wendisch, V.E (2015) Fermentative production of the diamine putrescine system metabolic engineering of Corynebacterium glutamicum. Metabolites, 5 (2), 211-231. 

Other anal sac constituents which are commonly encountered products of microbial activity include trimethylamine, noted in the anal sac secretions of the red fox (42), coyote and domestic dog [36), and the aromatic acids phenylacetic acid and 3-phenyl-propionic acid (and related phenolic acids), together with the diamines putrescine and cadaverine as well as ammonia in the anal sac secretions of the red fox and the lion (25,29,35). Indole has also been noted. The lower molecular weight lipids of lion anal sac secretion include many substances expected as hydrolysis products of sebaceous lipids (2. Red fox anal sac secretion also exhibits an anomalous free amino-acid composition with 5-aminovaleric acid predominating ( ). The possibility that the sulfur-containing volatiles present in mustelid anal sac secretions are of microbial origin is at present under investigation in our laboratories. 

Polyamines (PAs) are involved in growth, development, and adaptation against various environmental changes in plants (Kusano et al. 2008 Alcdzar et al. 2010 Bassard et al. 2010 Handa and Mattoo 2010 Mattoo et al. 2010 Takano et al. 2012). Major plant PAs are the diamines putrescine (Put) and cadaverine (Cad, abundant in legumes), the triamine spermidine (Spd), and the tetraamines spermine (Spm) and thermospermine (T-Spm). Cellular PA levels are regulated with a... 

The diamines, putrescine and cadaverine, are even more unpleasant smelling (Figure 4.3). They are formed in rotting animal and fish tissue by the breakdown of amino acids and their odor is associated with these, but they are also found in urine and semen, and they are part of major metabolic pathways. Recently, the production of putrescine in... 

Polyamines (PAs) are biologically ubiquitous aliphatic nitrogen-containing compounds of low molecular weight and polycationic nature. The diamine putrescine and the triamine spermidine are probably synthesized by all orga-... 

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