Putrescine - 1,4-Diaminobutane

the supply of blo-based polymer components. In particular the supply of diamines from biological sources for economic production, remains a challenge [6, 12, 13]. Approaching this Issue, systems and synthetic metabolic engineering has meanwhile tailored the prominent industrial workhorses Escherichia coli [14, 15] and Corynebacterium glutamicum [16-18] for de novo biosynthesis of promising diamines from renewable resources. This chapter highlights recent achievements in this field In the context of a future and sustainable bioeconomy. 

Putrescine (diaminobutane, DAB) is a widely abundant biogenic diamine [7]. It found early apphcation in the polymer industry as a building block for the synthesis of PA4.6, though not of biological origin [25]. Indeed, current production relies on propylene from petrochemistry, ammonium, and hydrocyanic acid [25]. The common occurrence in bacteria [7], however, promised a reasonable basis for bio-based production, thus stimulating research on fermentation processes. 

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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 ... 

A group of related siderophores comprises the desferri- or deferriferrioxamines (occasionally abbreviated as desferrioxamines) or proferrioxamines. Originally they were obtained from Actinomycetes, mainly Nocardia and Streptomyces spp. (187) and later found to be produced also by Erwinia spp. (several representatives) (e.g. (30a, 113,115,180)), Arthrobacter simplex (B), Chromobacterium violaceum (E) (246a), and by Pseudomonas stutzeri (several) (229a, 246,398). They consist of three (or in rare cases four) mono-N-hydroxy-l,4-diaminobutane (putrescine), mono-iV-hydroxy-l,5-diaminopentane (cadaverine) or (rarely) mono-N-hydroxy-1,3-diaminopropane units connected by succinic acid links. The hydroxylated terminus carries an acetyl or a succinyl (as in the structural formula heading Table 6)... 

Dead mice are as attractive as live mice, and dead mouse odor is as active as a dead mouse (Shivik and Clark, 1997). Elucidation of the feeding stimuli used by this species will aid in effective trapping for snake control. Fractions of dead mouse odor are being bioassayed. The best known constituents of rotting carcass (e.g. fish) odor, putrescine (1,4-diaminobutane NH2CH2CH2NH2) and cadaver-ine (NH2CH2CH2CH2NH2) were not active. 

Tabor CW, Tabor H (1976) 1,4-Diaminobutane (putrescine), spermidine, and spermine. Ann Rev Biochem 45 285-306... 

Diaminobutane dihydrochloride (putrescine hydrochloride) [333-93-7] M 161.1, m >290 . Crystd from EtOH/water. 

Other plant bioactive amines include a variety of neuroactive compounds and polyamines. Notable polyamines include cadaverine (1,5-diaminopentane), putrescine (1,4-diaminobutane), spermidine (NH2—(GH2)3—NH—(CH2)3—NH2), spermine (NH2—(CH2)3— NH-(CH2)3-NH-(GH2)3-NH2) and agmatine (NH2-C(=NH) CH2),-NH2). 

Benefits from MYCLAz targeting through its linkage to 1,3-diaminopropane and 1,4-diaminobutane (putrescine) as tumor finders are as follows ... 

SYNS BUTYLENEDIAMINE 1,4-BUTYLENE-DIAMINE 1,4-DIAMINOBUTANE PUTRESCIN PUTRESCINE TETRAMETHYLENEDIAMINE 1,4-TETRAMETHYLENEDIAMINE... 

The first successful polyamine separations were accomplished in the mid 70s after the introduction of surface-sulfonated cation exchangers. Fig. 3-164 displays a standard chromatogram with the separation of putrescine (1,4-diaminobutane) and cadaverine (1,5-diaminopentane) as well as spermidine (A-(3-aminopropyl-1,4-diaminobutane) and... 

As the name suggests, diamine oxidase catalyzes the oxidative deamination of diamines. Preferably a,co-diamines such as putrescine (1,4-diaminobutane) or cadaverine (1,5-diaminopentane) (the names already suggest their smell), but also various derivatives are readily converted. Quite often cyclic imines are obtained via internal nucleophilic attack by the unreacted amino function (Fig. 16.7-16) l38 40l. 

Putrescine and cadaverine are two odoriferous amines that are produced by decaying flesh. Putrescine is 1,4-diaminobutane, and cadaverine is 1,5-diaminopentane. Draw the structures of these two compounds. 

P.ll) (P-11) 1,4-Butanediamine, butane-1,4-diamine, tetramethylenediamine, tetramethylenediazane, butylenediamine, 4-aminobutylamine, 1,4-diaminobutane, putrescine [110-60-l[... 

Polyamines are low-molecular-weight molecules which are found in both prokaryotes and eukaryotes, and which fulfil essential needs for growth, division and differentiation. The most common poly amines are putrescine (1,4-diaminobutane tetramethylene-diamine), spermidine (N-(3-aminopropyl)-l,4-butane diamine) and spermine (N,N -bis(3-aminopropyl)-1,4-butane diamine). Cadaverine (1,5-diaminopentane) is also found in some micro-organisms (1,2). Most prokaryotes do not contain spermine but all cells contain putrescine and spermidine, in most cases in millimolar concentrations. 

Metcalf et al. (23) reported the synthesis of efiornithine (difluoromethyl ornithine [DFMO]) in 1978. Their interest arose from the desire to prepare ornithine decarboxylase (ODC) inhibitors as tools for studying the role of polyamines as regulators of growth processes. Ornithine decarboxylase catalyzes the conversion of ornithine to putrescine (1,4-diaminobutane), which in turn leads to the formation of the polyamines, spermine, and spermidine. It was not until 1980 that Bacchi et al. (24) demonstrated the potential of DFMO in the treatment of trypanosomiasis. 

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