Morpholine degradation

Combourieu B, P Besse, M Sancelme, H Veschambre, AM Delort, P Poupin, N Truffaut (1998) Morpholine degradation pathway of Mycobacterium aurum MOl direct evidence of intermadiates by in situ H nuclear magnetic resonance. Appl Environ Microbiol 64 153-158. 

Schrader T, Schuffenhauer G, Sielaff B, Andreesen JR (2000) High morpholine degradation rates and formation of cytochrome P450 during growth on different cyclic amines by newly isolated Mycobacterium sp. Strain HE5 Microbiol 146 1091-1098... 

Poupin P, N Truffaut, B Combourieu, M Sancelelme, H Veschambre, AM Delort (1998) Degradation of morpholine by an environmental Mycobacterium strain involves a cytochrome P-450. Appl Environ Microbiol 64 15-165. 

Initiation of the degradation of morpholine by a strain of Mycobacterium strain RPl (Poupin et al. 1998), and additionally of pyrrolidine and piperidine. 

This has received widespread application, and a single example has been chosen as representative. The pathway for the degradation of morpholine by Mycobacterium aurum MOl sadMycobacterium strain RPl was examined using whole cells, and this confirmed its identity to the one that had been proposed earlier for M. chelonae (Combourieu et al. 1998 Poupin et al. 1998). 

Detection of glycolate and 2-(2-aminoethoxy)acetate as intermediates in the degradation of morpholine by Mycobacterium aurum strain MOl (Combourieu et al. 1998). 

Poupin P, Godon JJ, Zumstein E, Truffant N (1999) Degradation of morpholine, piperidine and pyrrolidine by microbacteria evidence for the involvement of a cytochrome P450. Can J Microbiol 45 209-216... 

The pharmacokinetics of minaprine (orally administered) in humans have been studied [ 146,147]. The bioavailability has been found to be excellent, and the pharmacokinetic parameters did not show a dose-dependency [147]. The binding of (41) to human serum proteins and erythrocytes has been investigated [148]. Minaprine has been found to undergo extensive biotransformation in different species, with major groups of metabolites derived from degradation of the morpholine subunit and from hydroxylation of the phenyl substituent [149-152],... 

Photolytic. Mathew and Khan (1996) studied the photolysis of metolachlor in water in the presence of kaolinite, montmorillonite, and goethite and fulvic acid under neutral and acidic conditions at 22 °C. Metolachlor degraded in all the treatments at both pH conditions. The rate of photolysis and degradation products formed was dependent on the duration of UV exposure, the initial pH of the solution, and the composition of the suspended/dissolved material. The following photoproducts identified included 2-hydroxy-A-(2-ethyl-6-methylphenyl)-A-(2-methoxy-l-meth-ylethyl)acetamide, 4-(2-ethyl-6-methylphenyl)-5-methyl-3-morpholine (major product forming at 74-84% yield), 8-ethyl-3-hydroxy-A-(2-methoxy-l-methylethyl)-2-oxo-l,2,3,4-tetrahydroquino-line, 2-chloro-A -(2-(l-hydroxyethyl)-6-methylphenyl)-7V-(2-hydroxy-l-methylethyl)acetamide, and 2-chloro-A -(2-ethyl-6-hydroxymethylphenyl)-A-(2-methoxy-l-methylethyl)acetamide. 

Peptides, when administered orally, are susceptible to degradation in the stomach by gastric enzymes and the proteinases of the pancreas and brush border of the small intestine. Their lifetimes in the plasma are often short due to rapid proteolysis and other metabolic processes. Early efforts were made to improve the resistance of renin inhibitors to hydrolysis in vivo by the use of blocking groups at the Eland C-terminii [39] and replacement of susceptible peptide bonds other than the renin cleavage site. Studies of SAR have shown that various N- and C-terminal groups, some based on the morpholine nucleus and derivatives of it, have a favorable effect on the duration of inhibition in the... 

Doherty, S., Guillard, C., and Pichat, P., Kinetics and products of the photocatalytic degradation of morpholine in Ti02 suspensions, /. Chem. Soc. Faraday Trans., 91(12), 1853, 1995. 

Zhao ZZ, Qin X-Z, Wu A, Yuan Y. Novel rearrangements of an N-oxide degradate formed from oxidation of a morpholine acetal substance P antagonist. J Pharm Sci 2004 93(8) 1957-1961. 

In the literature, the simultaneous formation of the major NMMO degradation products N-methylmorpholine, morpholine and formaldehyde [20] is always attributed to the disproportionation of the primary aminyl radical 3, as a - not further defined - redox process between two molecules of 3, in which one is reduced to N-methylmorpholine (2) and the other oxidized to N-(methylene)morpholinium cation (17), which upon addition of water, forms morpholine and formaldehyde. Also this disproportionation can be rationalized as a radical coupling reaction which proceeds through recombination of N-centered 3 and C-centered 4, via the ammonium aminal intermediate 16 as the actual recombination product (Scheme 6). The intermediacy of this species was indeed confirmed by isolation from the reaction mixture and full characterization [17]. Compound 16 is quite labile and immediately de-... 

In heated DMAc/LiCl, the keteniminium ions are generated in situ from the solvent. When the degrading agent was added externally in the form of a keteniminium precursor, cellulose degradation was even more pronounced. The thermolabile keteniminium precursor compound 4-(l-chloro-2-methyl-propenyl)morpholine (54) immediately releases keteniminium ions 55 upon thermal treatment (Scheme 22) [71]. Addition of the precursor in very small... 

Further work in the area of the structural characterization of impurities and degradants of pharmaceuticals was also reported from the author s laboratories in 1999.107 First, the susceptibility of the morpholine substituent in the oxazolidinone antibiotic linezolid (41) was characterized using micro-NMR probe capabilities. Beginning from linezolid (41) photo-oxidation produced a transient pink color in... 

The morpholine enamines (343) and (344) in the etiojervane series were degraded by photo-oxygenation to give the corresponding ketones (345) and (346),... 

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