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PubMed2003

Visual and ocular changes associated with exposure to two tertiary amines.

AIMS: To determine if exposure to dimethylisopropanolamine (DMIPA) and dimethylaminoethanol (DMAE) in a label printing plant was associated with visual disturbances and/or ocular changes. METHODS: Questionnaires, eye examinations (visual acuity, contrast sensitivity at 2.5% and 1.25% contrast, slit lamp biomicroscopy, and pachymetry), and industrial hygiene monitoring for DMIPA and DMAE were performed over a two week period. RESULTS: Eighty nine per cent of line workers reported having experienced blurry vision while at work in the past 12 months, compared to 12.5% of prime workers. A total of 108 full shift personal breathing zone (PBZ) air samples for the amines were collected. The mean time weighted average (TWA) concentration of DMIPA was significantly higher in the line division than in the prime division, as was the mean TWA concentration for total amines. The mean TWA concentration of DMAE was higher in the prime division than the line division. Higher levels of total amines were associated with increased risk of reporting blurry vision, halo vision, and blue-grey vision. The risk of corneal opacity rose with increasing exposure to total amines. The prevalence of corneal opacity also increased with increasing concentration of total amines. Median corneal thickness increased with increasing grades of corneal opacity. There was a statistically significant relation between total amine concentration and increased risk of reduced bilateral visual acuity and 2.5% contrast sensitivity. CONCLUSIONS: Exposure to tertiary amines was associated with blurry, halo, and blue-grey vision, corneal opacity, and decrements in visual acuity and contrast sensitivity at 2.5% contrast.

Amines↗
PubMed1976

Kinetic effect of some aliphatic amines on yeast alcohol dehydrogenase.

Initial rate studies of ethanol oxidation catalyzed by yeast alcohol dehydrogenase (EC 1.1.1.1) were carried out in the presence of varying concentrations of aliphatic amines over the pH range from 8.0 to 10.5. Aliphatic amines either activate or inhibit the enzyme depending on whether the pH is greater or less than 9.5 suggesting that the protonated amines activate and the nonprotonated amines inhibit the enzyme. Aliphatic amines activate yeast alcohol dehydrogenase by decreasing Kb while they inhibit the enzyme by increasing both Ka and Kia. When both protonated and nonprotonated amines are present in solution, either overall activation or inhibition will be observed depending on the relative concentration of the two amine species.

Alcohol Oxidoreductases↗
PubMed1979

Amine content of vaginal fluid from untreated and treated patients with nonspecific vaginitis.

We examined the vaginal washings from patients with nonspecific vaginitis (NSV) to seek biochemical markers and possible explanations for the signs and symptoms of this syndrome. Seven amines were identified including methylamine, isobutylamine, putrescine, cadaverine, histamine, tyramine, and phenethylamine. These amines may contribute to the symptoms of NSV and may contribute to the elevated pH of the vaginal discharge. They may also be partly responsible for the "fishy" odor that is characteristic of vaginal discharges from these patients. Among the seven amines, putrescine and cadaverine were the most abundant and were present in all vaginal discharges from each of ten patients before treatment. These amines are produced in vitro during growth of mixed vaginal bacteria in chemically defined medium, presumably by decarboxylation of the corresponding amino acids. We hypothesize the anaerobic vaginal organisms, previously shown to be quantitatively increased in NSV, are responsible for the amine production, because metronidazole inhibited the production of amines by vaginal bacteria in vitro, and Haemophilus vaginalis did not produce amines. H. vaginalis did release high concentrations of pyruvic acid and of amino acids during growth in peptone-starch-dextrose medium, whereas, other vaginal flora consumed both pyruvic acid and amino acids in the same medium during growth. These findings suggest that a symbiotic relationship may exist between H. vaginalis and other vaginal flora in patients with NSV.

Amines↗
PubMed1997

Effect of amine activators on the properties of chemical cured dental composites.

The purpose of this study was to evaluate the reactivity and the effect of concentration of three tertiary amines upon the mechanical properties of a chemical curing dental composite. Chemical cured composite pastes were prepared by keeping peroxide concentration constant at 1 wt% (by weight of resin mixture) and by varying the amine/peroxide molar ratio from 0.25 to 1.5. Composite samples were prepared for all three amine pastes aged for 1, 15, 30, 45, and 60 d stored at 8, 22, and 37 degrees C. The loss in activity of the tertiary amine with time was measured. Changes in compressive strength, diametral tensile strength, and microhardness were also measured. A sharp decrease in working and setting times corresponding to increased activity was noticed with an increased amine content. The activity was found to vary in the order N,N-dimethyl p-toluidine (DMPT) > 2-(4-dimethylaminophenyl)ethanol (DMAPEA) > N,Ndiethanol p-toluidine (DEPT). DMPT is found to be more temperature sensitive than DMAPEA and DEPT. However, DEPT is found to provide better storage stability out of all three amines tested. Each amine was found to possess optimum concentrations at which the mechanical properties showed maximum values. DEPT is preferred for long-term storage stability in chemical-cured dental composites where aging tends to reduce the activity of the amine.

Amines↗
PubMed1990

Mechanisms and products of azo coupling in histochemical protease procedures based on primary aromatic amines as unspecific moieties.

It is presumed that the azo dyes generated by histochemical protease reactions are formed by substitution of a reactive aromatic carbon. They are referred to as dyes of the C-azo series. To confirm this assumption, the absorption spectra between 330 and 630 nm of azo dyes resulting from coupling between various aromatic amines of the aniline and naphthylamine series and the diazonium salts Fast Blue B and Fast Garnet GBC were studied in test tube experiments. Some of the amines were blocked by methylation to prevent coupling either at the amino group (N-methylated) or at the aromatic nucleus (C-methylated). Coupling was performed in buffered aqueous solutions of the diazonium salts. For analysis the azo dyes were dissolved in dimethylformamide. For acid rearrangement these solutions were acidified and incubated at elevated temperatures. After detection of dipeptidyl peptidase IV in tissue sections using Gly-Pro-4-methoxy-2-naphthylamine as substrate, the resulting dye was extracted and compared with the test tube compounds. All aromatic amines yielded azo dyes. Dyes extracted from sections and those test tube compounds derived from unmethylated or C-methylated amines showed almost identical spectral maxima, whereas dyes formed by N-methylated amines yielded different spectra. Acid rearrangement did not influence the spectral maxima of the N-methylated amine-derived dyes. Dyes resulting from C-methylated amines were destroyed. The results indicate that under histochemical conditions diazonium salts react primarily with the liberated free amino group but not with the aromatic nucleus of the unspecific moiety. Therefore, it is proposed that the formula of the final reaction product in naphthylamine-based protease histochemistry should be given as an N-azo dye, e.g., as a triazene.

Amines↗
PubMed2003

The effects of chronic administration of inhibitors of flavin and quinone amine oxidases on imidazoline I(1) receptor density in rat whole brain.

Many imidazoline ligands have been shown to bind to the active sites of several amine oxidases, and endogenous ligands such as agmatine and tryptamine are amine oxidase substrates. In order to ascertain whether concentrations of endogenous imidazoline receptor agonists might be regulated by amine oxidase activities, rats were administered saline, clorgyline, deprenyl, MDL 72274A, aminoguanidine, or a combination of clorgyline, deprenyl, and aminoguanidine, for 14 days, and then binding parameters for [(3)H]clonidine at imidazoline I(1) receptors were determined in whole brain. Several EC 1.4.3.4, 1.4.3.6, and 1.5.3.11 amine oxidase activities were also measured ex vivo in tissues from treated animals. Results showed that drug treatments did not alter the affinity of clonidine for imidazoline I(1) receptors. There was a tendency toward a reduction in receptor density when monoamine oxidase (MAO)-A 1 MAO-B, MAO-B 1 semicarbazide-sensitive amine oxidase (SSAO), or SSAO 1 diamine oxidase (DAO) were inhibited, and a marked reduction in density when MAO-A 1 MAO-B 1 SSAO were inhibited. These data suggest that amines that are substrates both for MAO and for SSAO, such as tryptamine and other trace amines, may act as endogenous imidazoline I(1) receptor agonists, at which they may have neuromodulatory efficacy. A role for beta-carbolines, which can form endogenously from tryptamine, is also supported by the present findings.

Adrenergic alpha-Agonists↗
PubMed1990

Involvement of cyclic AMP in multiple, excitatory actions of biogenic amines on the cardiac ganglion of the horseshoe crab Limulus polyphemus.

Cyclic AMP appears to be involved in several excitatory actions of amines on neurones of the Limulus cardiac ganglion. Amines selectively increase levels of cardiac ganglion cyclic AMP with a magnitude and time course similar to that observed for amine-induced excitation of cardiac ganglion burst rate. With respect to either the physiological or biochemical effect, the apparent order of potency is octopamine greater than epinephrine approximately dopamine greater than norepinephrine. Elevation of cardiac ganglion cyclic AMP levels by octopamine or dopamine is dose-dependent and is potentiated by the phosphodiesterase inhibitor 3-isobutyl 1-methylxanthine (IBMX). Several pharmacological agents which influence cyclic nucleotide metabolism, including forskolin, IBMX and 8-substituted cyclic AMP analogues, have amine-like effects on the Limulus cardiac ganglion. These effects include increased burst rate of the isolated cardiac ganglion and decreased burst duration, interburst interval and number of spikes per burst in follower neurones. Forskolin and IBMX increase levels of cardiac ganglion cyclic AMP, and IBMX also increases cyclic GMP levels in this tissue. Amines, forskolin and IBMX have direct effects on follower neurones pharmacologically isolated from pacemaker cell input. Octopamine, forskolin and IBMX depolarize follower neurones, while dopamine hyperpolarizes these cells. Amines, forskolin and IBMX elicit burst-like potentials in follower neurones, and increase the size of evoked, unitary junction potentials recorded in cardiac muscle fibres. These pharmacological and biochemical data suggest that multiple, excitatory effects of biogenic amines on the Limulus cardiac ganglion are mediated by simultaneous increases in cyclic AMP at several loci within this neural network.

1-Methyl-3-isobutylxanthine↗
PubMed1982

Effects of amine substances on susceptibility of cells to agglutination by concanavalin A and on paracrystal formation by vinblastine in untransformed 3T3 cells.

The effects of a secondary amine (ketamine), tertiary amines (dibucaine, lidocaine, marcaine, propanidid, diazepam and chlorpromazine) and a quaternary amine (tetraethylammonium bromide, TEA) on mouse 3T3 cell agglutination by concanavalin A (Con A), on patch formation of Con A receptors on the cell surface, and on paracrystal formation by vinblastine in cytoplasm were studied. These amines enhanced the cell agglutination at low concentrations of Con A, as did the mixture of colchicine and cytochalasin B. Ca++, applied extracellularly, inhibited the effects of these amines on cell agglutination by Con A. The patch formation of Con A receptors on the cell surface as revealed by fluoresceinated Con A was enhanced by these amines. Ketamine, dibucaine and TEA inhibited the paracrystal formation in cytoplasm, as did Ca++ ionophores such as A-23187 and X-537-A. These results suggest that the amines tested affect the fluidity of Con A receptors by impairment of cell membrane structural proteins and result in the increase of the susceptibility of cells to agglutination by Con A.

Agglutination↗
PubMed2004

Toxicity of model aliphatic amines and their chlorinated forms.

Aliphatic amines can be found in many wastewater effluents from industry, agriculture, pharmacy, and food processing. Amines can induce toxicological responses that are relevant in biochemical treatment processes, as well as in natural waters. This research compared the toxicity and inhibition caused by three aliphatic amines (n-propylamine, ethylmethylamine, and trimethylamine) and their chlorinated derivatives. The chemistry of chlorine interactions with these compounds was characterized by using membrane introduction mass spectrometry (MIMS). Acute toxicity assays were conducted by using a Microtox system with Phosphobacterium phosphoreum (also known as Vibrio fischeri) for the aliphatic amine compounds and their corresponding chlorinated derivatives, as identified by MIMS. Inhibition tests were conducted by using the oxygen utilization rate test with an enhanced nitrifier culture. The median effective concentration (EC50) values for chloropropylamine, chloroethylmethylamine, and chlorodimethylamine obtained by Microtox with a contact time of 15 min were 12.68, 19.72, and 15.92 microM, respectively. The EC50 values of these aliphatic chloramines from the Microtox test decreased by roughly one order of magnitude as a result of chlorination. Inhibition of nitrifiers also was observed in these amines. Trimethylamine and n-propylamine caused greater inhibition to nitrifiers than did ethylmethylamine under similar concentrations. Nitrifier inhibition from these amines increased after chlorination. The results of these tests indicated that aliphatic amines and their chlorinated derivatives could induce environmentally relevant toxicity responses in treatment settings and in receiving waters.

Amines↗
PubMed1986

Metabolic activation of mutagenic heterocyclic aromatic amines from protein pyrolysates.

Mutagenic heterocyclic amines are metabolized to mutagens which act directly on Salmonella typhimurium by P-448 forms of cytochrome P-450. These direct mutagens are N-hydroxylated heterocyclic amines, such as N-hydroxy-Trp-P-1, N-hydroxy-Trp-P-2, N-hydroxy-Glu-P-1, N-hydroxy-Glu-P-2, N-hydroxy-IQ, N-hydroxy-2-amino-alpha-carboline (N-hydroxy-A alpha C), and N-hydroxy-2-amino-3-methyl-alpha-carboline (N-hydroxy-MeA alpha C). The treatment of rats with polychlorinated biphenyl stimulated N-hydroxylation of heterocyclic amines about 10- to 260-fold depending on the substrates used. The N-hydroxylation activities of purified cytochrome P-448-H and P-448-L were markedly different. P-448-H, which had very low activity for benzo[a] pyrene metabolic activation, showed high N-hydroxylation activity. The activity ratio P-448-H:P-448-L was markedly different depending on the amines used. This ratio was 45, 22, 3, and 0.02, respectively, for Glu-P-1, IQ, Trp-P-2, and benzo[a] pyrene. On the other hand, N-acetylation of the heterocyclic amines was very low. Although marked species differences in the N-acetylation were observed, the activities of the heterocyclic amines were about 1/100 of that of 2-aminofluorene. N-Hydroxy-Trp-P-2 could react directly to DNA, but N-hydroxy-Glu-P-1 could not. Therefore we need to consider the presence of a further activating system in mammalian and bacterial cells. We observed that N-hydroxy-Trp-P-2 was activated by prolyl-t-RNA synthetase, but N-hydroxy-Glu-P-1 was not activated by the same system. In the bacterial cells, both N-hydroxy-Trp-P-2 and N-hydroxy-Glu-P-1 were not activated by prolyl-t-RNA synthetase. However, both hydroxylamines were activated by the acetyl-CoA-dependent mechanism in mammalian and bacterial cells. These results indicated that the O-acetylation is an important pathway for DNA damage by heterocyclic amines in chemical carcinogenesis.

Amines↗
PubMed1981

Effects of branched and straight chain amines and azasteroids on blood and egg cholesterol of White Leghorn chickens.

Six branched and straight chain secondary or tertiary amines with chain lengths of 12 to 18 carbons and two azasteroids, 25-aza-5 alpha-cholestane and 25-azacoprostane, were fed to mature White Leghorn hens, and their effectiveness was compared with 20,25-diazacholesterol dihydrochloride (SC-12937), an azasteroid known to lower egg cholesterol. Feed consumption, body weight, egg production, egg and plasma cholesterol and desmosterol, and plasma total lipid were measured. The 6 amines were fed at 200 ppm, and only the C12 branched chain amine N,N,3,711-pentamethyldodecanamine reduced plasma and egg cholesterol with a concomitant increase in desmosterol. After 4 weeks, plasma desmosterol was 0, 13, 60, and 75% of total sterol for control, 200 ppm C12 branched chain amine, 5 ppm diazacholesterol, and 5 ppm azacholestane, respectively. Egg production was severely reduced to 6 and 0% by feeding 5 ppm azacholestane for 2 and 4 weeks, respectively, and to 69 and 36% by feeding 5 ppm diazacholesterol. After 4 weeks egg cholesterol was 79 and 36% of the total sterol for the 200 ppm C12 branched chain amine and 5 ppm diazacholesterol, respectively. Concomitant increases in desmosterol accompanied all reductions in cholesterol. The depletion and repletion rates of egg cholesterol were measured in a subsequent experiment. After 2-1/2 weeks of feeding the test substances, egg cholesterol was reduced with concomitant increases in desmosterol. Egg cholesterol was 100, 71, and 50% of the total egg sterol for control, 200 ppm, and 400 ppm C12 branched chain amine, respectively: 58, 13, and 3% for .1, .5, and 1.0 ppm azacholestane; 28, 29, and 18% for 1, 2.5, and 5 ppm azacholesterol; and 23% for 1 ppm azacoprostane. The experimental diets were then withdrawn, and egg cholesterol repletion was studied biweekly. Egg cholesterol was repleted to 100% of the total sterol after withdrawal times of 2 weeks for C12 branched chain amine, 8 weeks for azacoprpostane, 14 to 16 weeks for diazacholesterol, 10 to 16 weeks for the lower levels of azacholestane, and longer than 16 weeks for 1 ppm azacholestane. The increase in desmosterol accompaning the demonstrated reduction in egg cholesterol, particularly with azasteroids, causes one to question the usefulness of this approach to lower cholesterol.

Amines↗
PubMed2000

Mixed starter cultures to control biogenic amine production in dry fermented sausages.

Several combinations of an amine-negative Lactobacillus sakei strain, along with proteolytic Staphylococcus carnosus or Staphylococcus xylosus strains, were used to study the influence of mixed starter cultures on biogenic amine production during the manufacture of dry fermented sausages. Changes in pH, water content, proteolysis, microbial counts, and biogenic amine contents were simultaneously examined in a spontaneously fermented batch and in three mixed starter-mediated batches. A double-controlled microbial charge initially inoculated as mixed starter culture of L. sakei and Staphylococcus spp. (all amine-negative strains) drastically reduced tyramine, cadaverine, and putrescine accumulation. No production of other aromatic amines such as histamine, phenylethylamine, or tryptamine was observed in any batch. The polyamines, spermine and spermidine, were found in raw materials and their levels decreased slightly in the spontaneously fermented batch. No correlation between proteolysis and biogenic amine production was observed. The use of proper technological conditions favoring starter development and the use of the raw materials with good hygienic quality make it possible to produce fermented sausages nearly free of biogenic amines.

Animals↗
PubMed2006

Biogenic amines in Portuguese traditional foods and wines.

The presence of biogenic amines in foodstuffs is an important food safety problem because of the implication of these compounds in food intolerance and intoxication. The separation and quantification of biogenic amines in foods is normally performed by chromatographic techniques. This review contains descriptions of the quantification of biogenic amines in Portuguese traditional fermented and/or ripened foods and wines, including Protected Denomination of Origin cheeses, dry-cured sausages, and Portuguese wines (including Port wines), using different analytical methods based on high-pressure liquid chromatography (UV or diode array and/or fluorometric detectors) and gas chromatography (with a mass spectrometry detector). The evolution of biogenic amines during fermentation, ripening, aging, or storage of those products was also evaluated. Biogenic amine concentrations ranged widely within individual food items, and storage, transport, and handling conditions can influence to some extent the biogenic amines present and their concentrations. Traditional foods are an important part of the Portuguese diet, and a high intake of harmful amounts of biogenic amines from traditional Portuguese fermented foods is possible. However, extensive research is needed to extend the current limited database.

Animals↗
PubMed1989

[Present aspects and problems regarding occupational bladder cancer due to exposure to aromatic amines].

About a century has passed since the first case of bladder cancer due to occupational exposure to carcinogenic aromatic amines was reported. In the major developed countries of the world, it is forbidden to manufacture and/or to use such aromatic amines. In Japan in the 1950's, many workers were exposed to carcinogenic aromatic amines, but in 1972, the Labor Safety and Health Act came into force and manufacturing and/or using of four kinds of aromatic amines were forbidden. Recently it has been reported that the risk of bladder cancer in workers exposed to aromatic amines before the ban of these chemicals is approximately from several times to a hundred times compared with the general population, and some reports say that dose-response relationship was observed. The important issues now are the carcinogenicity of other kinds of aromatic amines besides benzidine and 2-naphthylamine, carcinogenicity of metabolites of several substances like synthetic dyes, and carcinogenic aromatic amines as impurities in substances imported from developing countries. The type of exposure to these carcinogens changes low level and long period exposures. In addition to the chemical or dye industries, an increased risk of bladder cancer was observed among workers handling leather and rubber and those engaged in printing, textile industries, hairdressing, truck driving and so on. In the future, it will be necessary to cooperate with the departments of epidemiology, toxicology and clinical medicine for the purpose of estimating the risk of these occupations and the health care administration of the exposed workers.

2-Naphthylamine↗
PubMed1992

Tyrosine codon corresponds to topa quinone at the active site of copper amine oxidases.

The recently discovered organic cofactor of bovine serum amine oxidase, topa quinone, is an uncommon amino acid residue in the polypeptide backbone (Janes, S. M., Mu, D., Wemmer, D., Smith, A. J., Kaur, S., Maltby, D., Burlingame, A. L., and Klinman, J. P. (1990) Science 248, 981-987). The amine oxidase gene from the yeast Hansenula polymorpha has been cloned and sequenced (Bruinenberg, P. G., Evers, M., Waterham, H. R., Kuipers, J., Arnberg, A. C., and Geert, A. B. (1989) Biochim. Biophys. Acta 1008, 157-167). In order to understand the incorporation of topa quinone in eukaryotes, we have isolated yeast amine oxidase from H. polymorpha. Following protocols established with bovine serum amine oxidase, yeast amine oxidase was derivatized with [14C]phenylhydrazine, followed by thermolytic digestion and isolation of a dominant radiolabeled peptide by high pressure liquid chromatography. Comparison of resonance Raman spectra for this peptide to spectra of a model compound demonstrates that topa quinone is the cofactor. By alignment of a DNA-derived yeast amine oxidase sequence with the topa quinone-containing peptide sequence, it is found that the tyrosine codon, UAC, corresponds to topa quinone in the mature protein. In a similar manner, alignment of a tryptic peptide from bovine serum amine oxidase implicates tyrosine as the precursor to topa quinone in mammals.

Amine Oxidase (Copper-Containing)↗
PubMed2005

[Determination of aliphatic amines by high performance liquid chromatography with fluorescence and atmospheric pressure chemical ionization detection and identification by mass spectrometry].

Aliphatic amines exist widely in nature. Therefore, quick and precise determination of aliphatic amines is of great significance. A simple and highly sensitive method based on the derivatization of aliphatic amines utilizing 1,2-benzo-3,4-dihydrocarbazole-9-acetic acid (BCAA) as the novel pre-column derivatization reagent followed by high performance liquid chromatography with fluorescence detection and online mass spectrometric identification was developed. Optimum derivatization was obtained by the reaction of aliphatic amines with BCAA at 50 degrees C for 15 min in the presence of 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide (EDAC) in acetonitrile solvent. The condition of derivatization was mild and the yield of derivative each aliphatic amine was higher than 94%. Derivatives were sufficiently stable to be efficiently analyzed by high performance chromatography without pretreatment. On a reversed-phase BDS-C18 column, twelve aliphatic amine derivatives (C8 - C12) were separated under gradient elution with baseline resolution. The precise determining aliphatic amines from soil and wastewater samples was obtained by post-column online mass spectrometric identification with atmospheric pressure chemical ionization (APIC) source under positive mode detection. The established method exhibited excellent reproducibility and recovery. Linear responses were observed with coefficients over 0.999 3. The detection limits (at signal-to-noise ratio of 3: 1) were 12 - 28 fmol.

Acetonitriles↗
PubMed1990

Electron spin resonance study of chloroplast photosynthetic activity in the presence of amphiphilic amines.

Electron spin resonance spectroscopy (ESR) was used to study the effects of amphiphilic amines of the carbamate, amide, and ester type and amine oxide on the photosynthetic system of spinach chloroplasts. The ESR signal II connected to the photosynthetic center PS II donor side was observed to diminish in the presence of amines, whereas that of PS I remained unchanged. The inhibition of PS II increased with the increasing of amine concentration. In the presence of amines, the light: dark chloroplast ESR signals ratio as well as the intensity of the ESR signal of unbound Mn2+ increased. It is suggested that the amphiphilic amines affect the structure of PS II and the electron transfer to PS I. The effects of the amines tested on the photosynthetic system correlate with their potency to perturb the lipid membrane structure.

Amines↗
PubMed1991

Stereochemical trends in copper amine oxidase reactions.

Copper amine oxidases (EC 1.4.3.6) exhibit atypical stereochemical patterns in the reactions they catalyze. Dopamine and tyramine are oxidized with abstraction of the pro-R hydrogen by the porcine plasma amine oxidase, the pro-S hydrogen by pea seedling amine oxidase and a net nonstereospecific proton abstraction by the bovine plasma enzyme. This provides the first example in which a reaction catalyzed by enzymes in the same formal class occurs by all three possible stereochemical routes. To assess the underlying mechanistic significance of this heterogeneity, we have established the stereochemical course of the oxidation of tyramine by five additional copper amine oxidases using 1H NMR spectroscopy. Reactions catalyzed by rabbit and sheep serum amine oxidases are nonstereospecific. These enzymes exhibit rare mirror image binding with differential flux through two opposite and stereospecific reaction pathways. Differential primary kinetic isotope effects are observed for each mode, 8 and 4.6 for pro-S abstraction and 2.6 and 2.7 for pro-R abstraction by the sheep and rabbit amine oxidases, respectively. Tyramine oxidations catalyzed by the soybean and chick pea amine oxidases and porcine kidney diamine oxidase, however, are all stereospecific, occurring with loss of the pro-S hydrogen at C-1. Solvent exchange profiles are consistent within each stereochemical class of enzyme; the pro-R and nonstereospecific enzymes exchange solvent into C-2 of product aldehydes, the pro-S enzymes do not.

Amine Oxidase (Copper-Containing)↗