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PubMed2006

Preparation of anion exchanger by amination of acrylic acid grafted polypropylene nonwoven fiber and its ion-exchange property.

To develop the polymeric adsorbent that possess anionic exchangeable function, PP-g-AA-Am fibers were prepared by photoinduced grafting of acrylic acid (AA) onto polypropylene (PP) nonwoven fibers and subsequent conversion of carboxyl group in grafted AA to an amine (Am) group by reaction with diethylene triamine (DETA). The amination of grafted AA increased with increase in the degree of grafting, the reaction time and temperature of the chemical modification process. Catalytic effect of metal chlorides such as AlCl(3) and FeCl(3) on the amination of grafted AA was significant but not essential to lead the amination. FT-IR and solid (13)C NMR data indicate that amine group was introduced into PP-g-AA fiber through amide linkage between grafted AA and DETA. The anion exchange capacity of PP-g-AA-Am fiber increased with increase in the degree of amination, but reached maximum value at about 60% amination of 150% grafted AA. PP-g-AA-Am fiber showed much higher maximum capacity for PO(4)-P and a similar capacity for NO(3)-N compared to commercial anion resins. Furthermore, the PP-g-AA-Am fiber also has adsorption ability for cations because of unaminated residual carboxyl group.

Absorption↗
PubMed1998

Assessment of glutaraldehyde crosslinking efficiency with an amine-specific fluorescent probe.

BACKGROUND: Crosslinking of heart valves with glutaraldehyde involves the binding of amine groups. We have developed a technique that provides an inverse measure of the degree of tissue fixation by quantifying the amount of unbound amines. METHODS: Whole aortic valves were exposed to 0.5% glutaraldehyde solution for 0, 1, 15, and 60 minutes, 6 hours, and 1 and 7 days. Frozen sections were exposed to carboxyfluorescein succinimidyl ester, a fluorescent amine-reactive probe. Images were acquired from each section and processed to separate pixels representing tissue from those representing background. An average fluorescent intensity for each image was calculated and related to the number of unbound amines by comparing with standards. RESULTS: The amount of uncrosslinked amines was observed to decrease exponentially with fixation time and achieved a plateau at 1 day of fixation. A significant difference in the amount of unbound amines also exists between valve leaflets fixed while connected to the root and those excised from the root before fixation. CONCLUSIONS: This amine measurement technique, being sensitive to spatially varying differences in chemical fixation, should be useful in evaluating the efficacy of new fixation protocols.

Amines↗
PubMed1994

Amine blockers of the cytoplasmic mouth of sodium channels: a small structural change can abolish voltage dependence.

Many drugs block sodium channels from the cytoplasmic end (Moczydlowski, E., A. Uehara, X, Guo, and J. Heiny. 1986. Isochannels and blocking modes of voltage-dependent sodium channels. Ann. N.Y. Acad. Sci. 479:269-292.). Lidocaine, applied to either side of the membrane, induces two blocking modes, a rapid, voltage-dependent open-channel block, and a block of the inactivated channel that occurs on a 1000-fold slower timescale. Here we describe the actions of several lidocaine-related amines on batrachotoxin(BTX)-activated bovine cardiac sodium channels incorporated into planar lipid bilayers. We applied blocking amines from the intracellular side and examined the structural determinants of fast, open-channel block. Neither hydroxyl nor carbonyl groups, present in the aryl-amine link of lidocaine, were necessary, indicating that hydrogen bonding between structures in the aryl-amine link and the channel is not required. Block, however, was significantly enhanced by addition of an aromatic ring, or by the lengthening of aliphatic side chains, suggesting that a hydrophobic domain strengthens binding while the amine group blocks the pore. For most blockers, depolarizing potentials enhanced block, with the charged amine group apparently traversing 45-60% of the transmembrane voltage. By contrast, block by phenylhydrazine was essentially voltage-independent. The relatively rigid planar structure of phenylhydrazine may prevent the charged amino end from entering the electric field when the aromatic ring is bound. The relation between structural features of different blockers and their sensitivity to voltage suggests that the transmembrane voltage drops completely over less than 5 A. We raise the possibility that the proposed hydrophobic binding domain overlaps the endogenous receptor for the inactivation gate. If so, our data place limits on the distance between this receptor and the intrapore site at which charged amines bind.

Amines↗
PubMed2002

Volatile N-nitrosamine inhibition after intake Korean green tea and Maesil (Prunus mume SIEB. et ZACC.) extracts with an amine-rich diet in subjects ingesting nitrate.

The formation of carcinogenic nitrosamines under simulated gastric conditions was studied during the incubation of amine rich food and nitrate, and its possible inhibition by adding kumquat, sweet orange, strawberry, garlic, kale juices, Maesil (Prunus mume) and green tea extracts. The strawberry, kale juices, Maesil and green tea extracts were equally effective in reducing the formation of N-nitrosodimethylamine (NDMA). The fruits of P. mume SIEB. et ZACC. (Korean name, Maesil) have been used as a traditional drug and health food in Korea. During four weeks of test (designated EW1, EW2, EW3 and EW4; experiment week 1, 2, 3 and 4 diets) volunteers consumed a diet of low nitrate and amine (EW1) and consumed a fish meal rich in amines as nitrosatable precursors in combination with intake of nitrate-containing drinking water without (EW2) or with Maesil and green tea extracts (EW3 and EW4, respectively). The intake of nitrate-containing drinking water (340 mg nitrate/100 ml) resulted in a significant rise in mean salivary nitrate and nitrite concentrations and in mean urinary nitrate levels. Mean urinary nitrate was increased to 455.0+/-66.2, 334.6+/-67.8 and 333.4+/-50.7 mg/18 h after the nitrate intake of EW2, EW3 and EW4, respectively. Significant increases in urinary dimethylamine and trimethylamine levels were observed in consumption of diets (EW2, EW3, and EW4) rich in amine and nitrate. Maesil and green tea extract in EW3 and EW4 enhanced the increase of urinary dimethylamine and trimethylamine levels. Urinary excretion of N-nitrosodimethylamine in consumption of diet rich in nitrate and amine (EW2) increased to 6504.4+/-2638.7 ng/18 h from 257.0+/-112.0 ng/18 h of low nitrate and amine diet (EW1). Korean green tea and Maesil extracts in nitrate and amine rich diet reduced the excretion of N-nitrosodimethylamine to 249.7+/-90.6 and 752.7+/-595.3 ng/18 h, respectively, compared with 6504.4+/-2638.7 ng /18 h after ingestion of TD1 diet.

Adult↗
PubMed1997

Polar and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues.

Fourteen cooked dishes with their corresponding pan residues were analysed for polar and non-polar heterocyclic amines using HPLC. The choice of foods, including beef, pork, poultry, game, fish, egg and sausages, was based on an investigation of an elderly population in Stockholm participating in an analytical epidemiological case-control study on cancer risks after intake of heterocyclic amines. The food items were prepared using normal household cooking practices, and to reflect the wide range of surface browning of the cooked dishes that would be encountered in this population, four cooking temperatures were used in the range 150-225 degrees C. For all food samples, the total amount of heterocyclic amines formed at 150 degrees C was less than 1 ng/g cooked product, and at 175 degrees C less than 2 ng/g. The highest concentrations of heterocyclic amines were detected in fillet of pork, reindeer meat and chicken breast fried at 200 and 225 degrees C and their corresponding pan residues. The total sum of 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline, 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine was about 1 microgram per 100 g portion (including pan residues) for reindeer meat and chicken breast, and between 1.9 and 6.3 micrograms per 100-g portion for fillet of pork. PhIP was the most abundant heterocyclic amine, identified in 73 of 84 samples, and the highest concentration of PhIP, 32.0 ng/g, was found in the pan residue from fillet of pork cooked at 225 degrees C. The non-polar heterocyclic amines 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole and 3-amino-1-methyl-5H-pyrido[4,3-b]indole were detected in the range of 0.5-7.4 ng/g in most foods cooked at 225 degrees C, and also in meat sauce prepared at 200 and 175 degrees C. The other heterocyclic amines tested for: 2-amino-3-methylimidazo-[4,5-f]quinoline, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, 2-amino-6-methyl-pyrido-[1,2-a:3',2'-d]-imidazole and 2-aminodipyrido-[1,2-a:3',2'-d]imidazole, were present only at very low or non-detectable levels. The low recoveries of the amino-alpha-carbolines 2-amino-9H-pyrido[2,3-b]indole and 2-amino-3-methyl-9H-pyrido[2,3-b]indole made it impossible to quantify them. However, the co-mutagenic substances 1-methyl-9H-pyrido-[3,4-b]indole and 9H-pyrido[3,4-b]indole were detected at levels of about 1-30 ng/g in most of the dishes cooked at 200 and 225 degrees C.

Amines↗
PubMed1983

Gas chromatographic analysis of bacterial amines as their free bases.

Columns of Chromosorb 103, Tenax-GC, Amine 220 plus potassium hydroxide on Chromosorb W, and Carbowax 20M plus potassium hydroxide on Chromosorb W were compared for their ability to separate bacterial amines as their free bases in aqueous solution. A 1.52 m X 0.6 cm O.D. column of Chromosorb 103 separated eleven amines when operated isothermally at 185 degrees C. A further four high-boiling amines could be separated at 240 degrees C. The other packings separated only eight amines isothermally, except for Tenax-GC which separated seven of the free bases. Chromosorb 103 performed less well than Carbowax 20 M plus potassium hydroxide with respect to number of plates or peak resolution. The maximum number of amines separated, thirteen, required Chromosorb 103 programmed from 170 degrees C to 230 degrees C at 3 degrees C min-1 after an initial holding time of 20 min. It was possible tentatively to identify amines in culture supernatant fluid of Proteus mirabilis, viz. ethylamine, isobutylamine and isoamylamine, after direct injection of culture supernatant fluid.

Amines↗
PubMed1997

Rapid gas chromatographic profiling and screening of biologically active amines.

An efficient method is described for the simultaneous determination of 57 amines including volatile aliphatic amines, nonvolatile polyamines and catecholamines present in aqueous samples. The method is based on two-phase isobutyloxycarbonylation (isoBOC) with a pH shift. In 1.0 M phosphate buffer at pH 7.5, phenolic hydroxyl groups were allowed to react with isobutyl chloroformate in the dichloromethane phase, and subsequently pH of the aqueous phase was increased to 12.0 for the reaction of basic amino functions. The resulting N(O)-isoBOC amines were recovered by solid-phase extraction using Chromosorb P in normal phase partition mode, with subsequent tert.- butyldimethylsilylation of the remaining hydroxyl groups for gas chromatographic analysis. Using this combined procedure, linear responses were obtained in the concentration range of 0.2-12 ppm, with correlation coefficients varying from 0.945 to 0.999 for most of the amines studied except for 5-methoxytryptamine (0.864). Temperature-programmed retention index (I) sets as measured on DB-5 and DB-17 dual-capillary columns of different polarity were characteristic of each amine and thus, useful in the screening for amines by computer I matching. When applied to saliva samples, the present method allowed rapid screening for each spiked amine and unspiked polyamines such as 1,3-diaminopropane, putrescine, cadaverine and spermidine.

Amines↗
PubMed1993

Black (air-cured) and blond (flue-cured) tobacco cancer risk. IV: Molecular dosimetry studies implicate aromatic amines as bladder carcinogens.

Tobacco smoking causes a major fraction of male urinary bladder cancers and the relative risk of bladder cancer is reported to be two to three times higher for smoking of black (air-cured) than for smoking of blond (flue-cured) tobacco. In molecular dosimetry studies to examine the hypothesis that aromatic amines in tobacco smoke are primarily responsible for bladder cancer, the higher bladder cancer risk in smokers of black tobacco was correlated with two to five times higher exposure to carcinogenic aromatic amines present in black tobacco smoke, notably 4-aminobiphenyl (ABP). For the same amount of smoking, black tobacco smokers had levels of ABP-haemoglobin (Hb) adducts 1.5 times higher and excreted a 1.8-fold higher level of urinary mutagens. These mutagens were characterised as aromatic amines, and included the heterocyclic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), a known mutagen and multiorgan/species carcinogen. In smoking volunteers, the ABP-Hb adduct level depended significantly on the acetylator and P-450IA2 phenotypes, being 1.3- to 1.5-fold lower in fast acetylators, slow/intermediate P-450IA2 individuals. The N-(deoxyguanosine-8-yl)-ABP adduct was a major smoking-related DNA adduct in bladder biopsies from surgical patients. It was also tentatively identified in exfoliated urothelial cells of smoking volunteers, who showed a significant and linear correlation between adduct levels of ABP with Hb and with deoxyguanosine in urothelial DNA; both were related to number of cigarettes smoked per day. Levels of several smoking-related DNA adducts in urothelial cells were 2-20 times elevated in smokers. Similar convex dose-response relationships have been found between the number of cigarettes smoked and the relative risk for bladder cancer and between the levels of ABP-Hb adducts and markers of recent smoking. A possible explanation is that fast and slow acetylators have different susceptibility to aromatic amine carcinogens. Case-control studies have consistently revealed an excess of variable magnitude of slow acetylators in subgroups exposed occupationally to carcinogenic aromatic amines. Altogether, results from these studies reinforce the association between cigarette smoking, carcinogen-DNA adducts in urothelial cells, and implicate primary aromatic and possibly heterocyclic amines as bladder carcinogens.

Amines↗
PubMed2002

Carcinogenicity of the aromatic amines: from structure-activity relationships to mechanisms of action and risk assessment.

Aromatic amines represent one of the most important classes of industrial and environmental chemicals: many of them have been reported to be powerful carcinogens and mutagens, and/or hemotoxicants. Their toxicity has been studied also with quantitative structure-activity relationship (QSAR) methods: these studies are potentially suitable for investigating mechanisms of action and for estimating the toxicity of compounds lacking experimental determinations. In this paper, we first summarized the QSAR models for the rodent carcinogenicity of the aromatic amines. The gradation of potency of the carcinogenic amines depended firstly on their hydrophobicity, and secondly on electronic (reactivity, propensity to be metabolically transformed) and steric properties. On the contrary, the difference between carcinogenic and non-carcinogenic aromatic amines depended mainly on electronic and steric properties. These QSARs can be used directly for estimating the carcinogenicity of aromatic amines. A two-step prediction is possible: (1) estimation of yes/no activity; (2) if the answer from step 1 is yes, then prediction of the degree of potency. The QSARs for rodent carcinogenicity were put in a wider context by comparing them with those for: (a) Salmonella mutagenicity; (b) general toxicity; (c) enzymatic reactions; (d) physical-chemical reactions. This comparative QSAR exercise generated a coherent global picture of the action mechanisms of the aromatic amines. The QSARs for carcinogenicity were similar to those for Salmonella mutagenicity, thus pointing to a similar mechanism of action. On the contrary, the general toxicity QSARs (both in vitro and in vivo systems) were mostly based on hydrophobicity, pointing to an aspecific mechanism of action much simpler than that for carcinogenicity and mutagenicity. The oxidation of the amines (first step in the main metabolic pathway leading to carcinogenic and mutagenic species) had identical QSARs in both enzymatic and physical-chemical systems, thus providing evidence for the link between simple chemical reactions and those in biological systems. The results show that it is possible to generate mechanistically and statistically sound QSAR models for rodent carcinogenicity, and indirectly that the rodent bioassay is a reliable source of good quality data.

Amines↗
PubMed1989

Polymeric activated ester reagents for off-line and on-line derivatizations of amine nucleophiles in high-performance liquid chromatography with ultraviolet and fluorescence detection.

A novel polymeric activated ester reagent has been developed that improves final detectability and chromatographic performance in high-performance liquid chromatography (HPLC) for virtually all primary and secondary amines or amine analogues. This has involved the synthesis, characterization of final reagent, optimization of derivatization and separation conditions, and determination of analytical figures of merit. The polymeric reagent contained an activated ester linkage to the 9-fluorenyl group, which imparted ultraviolet (UV) and fluorescence (FL) detector properties to the final derivatives. Kinetic studies of these solid-phase (heterogeneous) reactions have been conducted, and specific rate constants were compared with those of the analogous solution reaction for the same substrates. Percent derivatizations have reached 90% and 70% for primary and secondary amines, respectively, under optimized conditions. High reaction reproducibility has been obtained by using the on-line approach, for more than 50 separate injections of the same amine substrate with a single solid-phase reactor. These solid-phase derivatizations have led to detection limits for typical amines in the low-parts-per-billion range. The final, overall methods can provide rapid, automatable, accurate, and precise detection and quantitation of primary/secondary amines and amine-like compounds in real-world sample matrices. As an illustrative example, amphetamine spiked in urine has been derivatized off-line and on-line, with minimum sample preparation, and detected via HPLC-UV/FL with acceptable accuracy and precision.

Amines↗
PubMed1994

Chemical rescue by exogenous amines of a site-directed mutant of ribulose 1,5-bisphosphate carboxylase/oxygenase that lacks a key lysyl residue.

Ligand binding to ribulose 1,5-bisphosphate carboxylase/oxygenase immobilizes the flexible loop 6 of the beta/alpha barrel domain in its closed conformation. Lys329, located at the apex of this loop, interacts electrostatically with Glu48 of the adjacent subunit and with the CO2-derived carboxylate of the carboxylated reaction intermediate [Knight et al. (1990) J. Mol. Biol. 215, 113-160]. Previous studies have implicated Lys329 in the addition of CO2 to the initial enediol(ate) intermediate: mutants at position 329 catalyze enolization of ribulose 1,5-bisphosphate and processing of isolated carboxyketone intermediate, but are severely impaired in overall carboxylation and the tight-binding of the carboxylated intermediate analogue 2-carboxyarabinitol 1,5-bisphosphate. Using the chemical rescue method of Toney and Kirsch [(1989) Science 243, 1485-1488], we show that these defects are partially overcome by exogenous amines. For example, ethylamine enhances the carboxylation rate of K329A by about 80-fold and strengthens complexation of 2-carboxyarabinitol 1,5-bisphosphate. The CO2/O2 specificity of K329A is increased by amines, but remains lower than the wild-type value. Despite the pronounced enhancement of carboxylase activity, amines do not influence the rate at which ribulose 1,5-bisphosphate is enolized by K329A. Rescue of K329A follows an apparent Brønsted relationship with a beta of 1, implying complete protonation of amine in the rescued transition state. Rate saturation with respect to amine concentration and the different steric preferences for amines between K329A and K329C suggest that the amines bind to the enzyme in the position voided by the mutation.(ABSTRACT TRUNCATED AT 250 WORDS)

Amines↗
PubMed1982

Myeloperoxidase-catalyzed incorporation of amines into proteins: role of hypochlorous acid and dichloramines.

Myeloperoxidase-catalyzed oxidation of chloride (Cl-) to hypochlorous acid (HOCl) resulted in formation of mono- and dichloramine derivatives (RNHCl and RNCl2) of primary amines. The RNCl2 derivatives could undergo a reaction that resulted in incorporation of the R moiety into proteins. The probable mechanism was attack of RNCl2 or an intermediate formed in the decomposition of RNCl2 on histidine, tyrosine, and cystine residues and on lysine residues at high pH. Incorporation of radioactivity from labeled amines into stable, high molecular weight derivatives of proteins was measured by acid or acetone precipitation and by gel chromatography and electrophoresis. Whereas formation of RNCl2 was favored at low pH, the subsequent incorporation reaction was favored at high pH. Up to several hours were required for the maximum amount of incorporation, which was less than 10% of the label in RNCl2. For the amines tested, incorporation was in the order histamine greater than 1,2-diaminoethane greater than putrescine greater than taurine greater than lysine greater than glucosamine greater than leucine greater than methylamine. Initiation of the reaction required HOCl, and oxidized forms of bromide, iodide, or thiocyanate did not substitute. Inhibitors of incorporation fell into three classes. First, ammonia or amines competed with the labeled amine for reaction with HOCl, so that larger amounts of HOCl were required. Second, readily oxidized substances such as sulfhydryl or diketo compounds or thioethers (methionine) reduced RNCl2. Third, certain compounds competed with protein as the acceptor for the incorporation reaction. The amount required to block incorporation into protein depended on protein concentration. Among these inhibitors were imidazole compounds (histidine), phenols (tyrosine), and disulfides (glutathione disulfide, GSSG). Low yields of derivatives of histidine, tyrosine, and GSSG were detected by thin-layer chromatography. Acid-precipitable derivatives were obtained by reacting RNCl2 with polyhistidine or polytyrosine, and to a lesser extent with polylysine at high pH, but not with other poly(amino acids). Precipitable derivatives were also obtained by incubating MPO-containing extracts from leukocyte granules with hydrogen peroxide, Cl-, and labeled amines. The extracts were found to have a high content of substances with primary amino groups, which competed for incorporation. The results account for oxidative incorporation of amines into proteins in leukocytes and provide evidence that HOCl and nitrogen-chlorine (N-Cl) derivatives are formed in these cells. The characteristics of the incorporation reaction suggest that it would not contribute significantly to the antimicrobial activity of myeloperoxidase (MPO). Nevertheless, the reaction may provide a sensitive method for studying MPO action in vivo.

Amines↗
PubMed2006

A comparative study of the binding and inhibition of four copper-containing amine oxidases by azide: implications for the role of copper during the oxidative half-reaction.

Copper amine oxidases (CuAOs) catalyze the oxidative deamination of primary amines operating through a ping-pong bi-bi mechanism. In this work, azide (an exogenous monodentate ligand) was used to probe the role of copper during the oxidative half-reaction of CuAO catalysis. The effects of azide on both the reductive and oxidative half-reactions of pea seedling amine oxidase (PSAO), the recombinant human kidney diamine oxidase (rhDAO), Arthrobacter globiformis amine oxidase (AGAO), and Pichia pastoris amine oxidase (PPLO) have been examined. For the reductive half-reaction, defined as the oxidation of amine substrate to an aldehyde, azide was discovered to exhibit either noncompetitive or competitive inhibition with respect to the amine, depending on the enzyme source. With regard to the oxidative half-reaction, defined as the reoxidation of the enzyme via reduction of O(2) to H(2)O(2), azide has been determined to exhibit competitive inhibition with respect to O(2) in PSAO with a calculated K(i) value that is in excellent agreement with the experimentally determined K(d) value for the Cu(II)-N(3)(-) complex. Azide was found to exhibit mixed-type/partially competitive inhibition with respect to substrate O(2) in rhDAO, with an apparent K(i) that is similar to the K(d) value for the Cu(II)-N(3)(-) complex. The competitive inhibition for PSAO and the partially competitive inhibition for rhDAO are consistent with O(2) interacting directly with copper during enzymatic reoxidation. For the enzymes AGAO and PPLO, pure noncompetitive and mixed-type/partially competitive inhibition is observed. K(i) values for reductive and oxidative half-reactions are equivalent and are lower than measured K(d) values for the Cu(II)-N(3)(-) complexes in oxidized and substrate-reduced forms of these enzymes. Given these observations, it appears that substantial inhibition of the reductive half-reaction occurs at the concentrations of azide used for the oxidative half-reaction experiments, thereby complicating kinetic interpretation. At this time, the data do not permit us to distinguish between two possibilities: (1) inhibition by azide with respect to O(2) is intrinsically competitive in CuAOs, but this effect cannot always be deconvolved experimentally from the effects of azide on the reductive half-reaction; or (2) CuAOs differ in some steps of their reoxidation mechanisms.

Amine Oxidase (Copper-Containing)↗
PubMed2003

Effect of steric hindrance on carbon dioxide absorption into new amine solutions: thermodynamic and spectroscopic verification through solubility and NMR analysis.

Acid gas absorption technology is of great importance in these days for the prevention of global warming and the resulting worldwide climate change. More efficient process design and development for the removal of acid gases has become important, together with the development of new absorbents as one of urgent areas of research in addressing global-warming problems. In the present work, aqueous solutions of 2-amino-2-hydroxymethyl-1,3-propanediol (AHPD), a sterically hindered amine, has been examined as a potential CO2 absorbent and compared with the most commonly used absorbent, monoethanolamine (MEA) solution, through equilibrium solubility measurements and 13C NMR spectroscopic analyses. The solubilities of CO2 in aqueous 10 mass % AHPD solutions were higher than those in aqueous 10 mass % MEA solutions above 4 kPa at 298.15 K, but below 4 kPa, the solubility behavior appeared to be the opposite. The solubility difference between these two solutions increased with the CO2 partial pressures above the crossover pressure. Equilibrated CO2-MEA-H2O and CO2-AHPD-H2O solutions at various CO2 partal pressures ranging from 0.01 to 3000 kPa were analyzed by 13C NMR spectroscopy to provide a more microscopic understanding of the reaction mechanisms in the two solutions. In the CO2-amine-H2O solutions, amine reacted with CO2 to form mainly the protonated amine (AMH+), bicarbonate ion (HCO3-), and carbamate anion (AMCO2-), where the quantitative ratio of bicarbonate ion to carbamate anion strongly influenced the CO2 loading in the amine solutions. A profusion of bicarbonate ions, but a very small amount of carbamate anions, was identified in the CO2-AHPD-H2O solution, whereas a considerable amount of carbamate anions was formed in the CO2-MEA-H2O solution. AHPD contains more hydroxyl groups than nonhindered MEA, and hence, the chemical shifts in its 13C NMR spectra were strongly influenced by the solution pH values. In contrast, MEA appeared to be insensitive to pH. The strong interrelations among CO2 solubility, CO2 partial pressure, bulkiness of the amine structure, and pH identified through the present experimental investigations can provide basic guidelines for finding new potential organic absorbents, including specifically designed amine chemicals.

Absorption↗
PubMed2002

Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin host.

A general chiroptical protocol for determination of absolute configuration of secondary amines including acyclic and cyclic aliphatic amines, aromatic amines, amino acids, and amino alcohols is described. The chiral substrate is linked to the achiral carrier moiety (3-N-Boc-amino-propyl-N-Boc-amino)acetic acid 1 (BocHNCH(2)CH(2)CH(2)BocNCH(2)COOH), which after deprotection, yields a bidentate conjugate, capable of forming a 1:1 host/guest complex with dimeric zinc porphyrin host 2. As in the cases of primary amines and secondary alcohols reported earlier, the complexation of secondary amine conjugates to porphyrin tweezer host 2 represents a stereodifferentiating process, where the large (L) group at the stereogenic center (assigned on the basis of conformational energies A value) protrudes from the porphyrin binding pocket. This leads to formation of host/guest complexes with a preferred porphyrin helicity that exhibit intense exciton split CD spectra. It was found that the chiral sense of porphyrin twist is clearly controlled by the stereogenic center despite the Z/E conformational complexity around the tertiary amide bond of secondary amine conjugates that has greatly hampered previous configurational assignments. Thus, in cases where there is no ambiguity regarding the relative steric size of substituents, the observed CD couplet can be applied for straightforward assignment of absolute configurations. In addition, to extend the application to more difficult cases a molecular mechanics calculation approach using the Merck Molecular Force Field (MMFFs) was developed; this provides conformational information of host/guest complexes and leads to prediction of preferred porphyrin helicity independent of conformational A values. This chiroptical protocol in combination with molecular modeling represents a general method for configurational assignments of secondary amines.

Amines↗
PubMed2002

Effects of high hydrostatic pressure treatments on biogenic amine contents in goat cheeses during ripening.

The application of high-pressure treatment to accelerate cheese ripening may influence the occurrence and profile of biogenic amines. In some cases, high-pressure treatment could yield high amine content, whereas in others the amine concentrations were comparable with those in nontreated ones. Tyramine was the most affected amine. However, the influence of high pressure depended on the treatment applied. The highest amine concentrations were observed when 50 MPa for 72 h was applied, and in which, the content of tyramine was almost three times higher than in the untreated samples. On the contrary, when 400 MPa for 5 min or 400 MPa for 5 min plus 50 MPa for 72 h were applied contents of this amine were similar or lower than those found in control cheeses showing similar degrees of proteolysis. The higher proteolysis, induced by the pressurization treatments, was not correlated with the higher amine production.

Amino Acids↗
PubMed2006

Study of amine composition of botrytized grape berries.

Aliphatic primary and biogenic amines of grape varieties from two vintages were studied. We established that appearance and/or increase of both primary aliphatic and biogenic amines is due to microbiota living in/on grape berries. Aszú, gray rotten grapes infected mainly with Botrytis cinerea, grape berries infected mainly with Penicillium species, and intact grape berries were compared on the basis of amine composition using t-test, analysis of variance, and multivariate statistical analysis (principal component analysis and linear discriminant analysis). The amine composition and amine content of Aszú grapes were significantly different (p < 0.05) from those of intact grapes despite the effect of the vineyards and the vintages. Grape samples coming from the same growing location, intact, Aszú grapes, and grape berries infected mainly with Penicillium species could be separated from each other with multivariate statistical analysis. We distinguished intact, Aszú (noble rotten), and gray rotten berries from each other as well. Evaluating amine values of grape samples independently of the place of origin, the Aszú and green rotten berries could not be differentiated. The varieties and vineyards have affected the amine composition of Aszú grapes, while these effects on intact grapes appeared only slightly.

Biogenic Amines↗
PubMed2006

General but discriminating fluorescent chemosensor for aliphatic amines.

Aliphatic amines are sensitively and discriminatively detected through binding with demethylated naphthol AS-BI (7-bromo-3-hydroxy-2-naphth-o-hydroxyanilide, 2) and fluorescence of the resulting complex. Recognition of the amine by the chemosensor 2 occurs via proton transfer of the naphtholic proton to the amine and is facilitated by the presence of the phenol group. Amine basicity is the primary controller of detection. Poorly basic aromatic and conjugated amines such as pyridine and aniline are not detected. Hydrogen bonding within the complex allows further differentiation of aliphatic amines. Doubly primary, conformationally flexible diamines are the most sensitive to detection, followed by secondary amines.

Amines↗