Deamination degradation

Few simple amines are known in either the furan or the benzo[Z>]furan series. Simple nitrofurans on attempted reduction by mild chemical methods suffer what is probably a deaminative degradation. Similarly, attempted reduction of 2-nitrobenzo[6]furan affords not the amine but the product of its hydrolysis, benzofuran-2(3/f )-one. 

At the other end of the reaction, deviations from idealized rate laws are attributed to secondary reactions such as degradations of acids, alcohols, and amines through decarboxylation, dehydration, and deamination, respectively. The step-growth polymers which have been most widely studied are simple... 

Strecker Degradation (Oxidative Deamination), Mild oxidizing agents such as aqueous sodium hypochlorite or aqueous A-bromosuccinimide, cause decarboxylation and concurrent deamination of amino acids to give aldehydes. 

Degradation Decarboxylation, deamination, dehalogenation, dehydroxylation, ring fission, demethoxylation, deacetylation... 

An interesting study examined the anodic oxidation of EDTA at alkaline pH on a smooth platinum electrode (Pakalapati et al. 1996). Degradation was initiated by removal of the acetate side chains as formaldehyde, followed by deamination of the ethylenediamine that formed glyoxal and oxalate. Oxalate and formaldehyde are oxidized to CO2, and adsoption was an integral part of the oxidation. 

Cook AM, R Hiitter (1984) Deethylsimazine bacterial dechlorination, deamination and complete degradation. J Agric Food Chem 32 581-585. 

In analogy with phenol, aniline is carboxylated to 4-aminobenzoate followed by reductive deamination to benzoate (Schnell and Schink 1991), which is degraded by pathways that have already been elaborated. 

Schnell S, B Schink (1991) Anaerobic aniline degradation via reductive deamination of 4-aminobenzoyl-CoA in Desulfobacterium anilini. Arch Microbiol 155 183-190. 

The gene tdnQ that encodes the oxidative deamination of aniline is carried on a plasmid in strains of Comamomas testosteroni and Delftia acidovorans. However, it has not been resolved whether this enzyme is involved in the degradation of 3-chloroaniline, because the gene is transcribed in the presence of aniline, but not when only 3-chloroaniline is present (Boon et al. 2001). 

FIGURE 10.3 Pathways for degradation of L-tryptophan by (a) tryptophanase, (b) deamination and oxidation, and (c) side-chain oxidation and decarboxylation to indole. 

The aerobic degradation of L-cysteate by Paracoccus pantotrophus is carried out by deamination to 3-sulfolactate from which sulfite is lost with the formation of pyruvate (Cook et al. 2006). The activity of the lyase (3-L-sulfolactatesulfolyase) has been shown to involve pyridoxal 5 -phosphate, and the enzyme has been found in a number of organisms using L-cysteate either as a source of carbon or as an electron acceptor (Denger et al. 2006). 

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