Aliphatic Monoamines Research Articles

Biosynthese aliphatischer monoamine in Mercurialis perennis durch aminosäure-aldehyd-transaminierung

Summary Aliphatic aldehydes, fed to shoots of Mercurialis perennis are transformed to the corresponding monoamines. The aminating activity can be demonstrated in particle free cell extracts. The corresponding enzyme-system is found to be an aminotransferase which catalyzes the transamination between amino acids and aldehydes. Using a partially purified preparation obtained from cell free extracts by precipitation with acetone at 80 % saturation some properties of the enzyme are investigated. The enzyme is rather unstable in solution. The reaction has an optimal temperature at 30° C and a pH optimum of 8.5. L-Alanine is found to be the most efficient NH 2 -donator. Substitution of alanine by L-glutamic acid, γ-aminobutyric acid or e-aminocaproic acid results in noticeably lower activity. Other amino compounds are ineffective. All aldehydes of the homologous series ethanal to undecanal are found to be active amino acceptors. No requirement of the enzyme for pyridoxal-5′-phosphate can be demonstrated but the reaction is sensitive to agents known to combine with carbonyl- and SH-groups. Several keto acids such as pyruvate, oxaloacetate or α-ketoglutarate are strong, probably competitive inhibitors of the aldehyde amination reaction. Deaminating activity of the enzyme system is somewhat lower than aminating activity. The function of the enzyme in biosynthesis of simple aliphatic monoamines is discussed. Biosynthesis of at least four out of six aliphatic amines we found to occur in Mercurialis can be explained by action of the aminotransferase. The occurrence of several lower aliphatic aldehydes, which presumably can serve as natural substrates of the enzyme is demonstrated in Mercurialis perennis . There is some doubt wheather the enzyme is a specific amino acid-aldehyde transaminase or an substrate unspecific amino acid-keto acid transaminase which also reacts with aldehydes.

Dünnschichtchromatographie der 2,4-dinitrophenylderivate wasserdampfflüchtiger amine und ihre anwendung auf die trennung pflanzlicher amine

Thin-layer chromatography of the 2,4-dinitrophenyl derivatives of simple steam volatile amines and its application to the separation of plant amines Three sovent systems are described for separating the dinitrophenyl derivatives of steam volatile amines (DNP-amines) on Silica Gel HF 254. The solvent system pentane—acetic acid-isoamylester—ammonia (70:29:1) is particularly useful for the separation of amines found in biological materials. The separation of higher homologous aliphatic monoamines, and the isomeric propylamines, butylamines, and amylamines, which is not practicable with these solvents, has been carried out successfully by using a chromagraphic system described by SCHWARTZ et al. 10. Some examples are given to illustrate the efficiency of this method. Thus the occurence of octylamine (apple fruit) and 2-methylbutylamine ( Lychnis coronaria) has been demostrated in plants for the first time. DNP-amines separated on Silica Gel H can be determined quantitatively by spectrophotometric methods after elution with methanol.

Cockroach amine oxidase: Classification and substrate specificity

1. 1. The amine oxidases of Malpighian tubules of Periplaneta americana L. and Blaberus discoidalis Serville accepted agmatine and short-chain aliphatic diamines as substrates; heptamethylene diamine was the subtrate most rapidly oxidized. 2. 2. The Blaberus enzyme did not act upon any monoamine tested. New substrates of the Periplaneta oxidase included the straight-chain aliphatic monoamines. 3. 3. These reactions were not inhibited by semicarbazide.

Purification and properties of an amine dehydrogenase from Pseudomonas AM1 and its role in growth on methylamine.

1. Whole cells of Pseudomonas AM1 grown on methylamine oxidize methylamine, formaldehyde and formate. Crude extracts oxidize methylamine only if supplemented with phenazine methosulphate. 2. By using a spectrophotometric assay, the methylamine-oxidizing enzyme has been purified 20-fold in 31% yield. 3. The enzyme is a dehydrogenase, unable to utilize oxygen, NAD, NADP, flavines or menadione as electron acceptors, but able to utilize phenazine methosulphate, ferricyanide, cytochrome c or brilliant cresyl blue. 4. The enzyme is non-specific, readily oxidizing aliphatic monoamines and diamines, histamine and ethanol-amine. Secondary and tertiary amines, quaternary ammonium salts and aromatic amines are not oxidized. 5. The pH optima for methylamine, n-pentylamine and putrescine are respectively 7.6, 8.0 and 8.5. 6. The K(m) value for methylamine is 5.2mum and that for phenazine methosulphate 56mum. 7. The enzyme will withstand heating for 15min. at 80 degrees without loss of activity, but is inactivated at higher temperatures. It is not inactivated by any pH value between 2.6 and 10.6. 8. The dehydrogenase is inhibited by semicarbazide (K(i) 3.35mum), isoniazid (K(i) 1.17mum), cuprizone (K(i) 0.49mum), p-chloromercuribenzoate (K(i) 0.45mm) and quinacrine (K(i) 12.1mm). 9. The enzyme is absent from succinate-grown cells, and, during adaptation from succinate to methylamine, activity appears before growth on methylamine begins.

Amine Oxidases of Microorganisms

With the crystalline preparations of amine oxidase of Aspergillus niger, some properties of the enzyme were investigated. The enzyme was stable in phosphate buffer of pH over the range of 6.0 to 7.0. On heating, the enzyme was stable up to 35°C, but, above 40°C, it was rapidly destroyed.The recrystallized enzyme was at least 90% pure when examined in the ultracentrifuge. The molecular weight was determined to be approximately 252,000. The enzyme was pink in color and shown an absorption maximum at about 480 m/μ. This absorption maximum was abolished by substrates as well as by sodium dithionite, and was restored by oxygenation.The enzyme oxidized preferentially aliphatic monoamines of C3—C6. The other monoamines, such as benzylamine, phenethylamine, histamine and agmatine, were oxidized as well. The aliphatic diamines of C4—C6 were oxidized but in rather low rates. The rates of oxidation showed optima at pH 7.5, 7.2, 7.8 and 8.6 for n-butylamine, benzylamine, histamine and putrescine, respectively.

Hydrogen bonding in amine–epoxide adducts

AbstractThe infrared spectra of several alcohols and aminoalcohols were measured in bulk and in dilute solution in the 2800–4000 cm.−1 region to determine the nature of hydrogen bonding in these compounds. An epoxy resin was cured with both an aliphatic monoamine and a diamine, and the OH‐stretching bands of the polymers were studied in the temperature range 30–200°C. It is concluded that the hydroxyl groups in the polymers are extensively involved in long‐range hydrogen bonding, particularly of the OHN type, at room temperature. The shift in the bonded OH band to lower frequency with increasing temperature is attributed to a shift from long range to short range bonds. Even at 200°C. there are relatively few free hydroxyl groups in these polymers.

Cell division: III. The effects of amines on the structure of isolated nuclei

Information on the condensation of chromatin by organic substances is of interest in relation to attempts to formulate the properties of the chromosomal condensant active during cell division. The relation of nuclear volume to concentration has therefore been studied. n-Propylamine, an example of an aliphatic monoamine, produced swelling in low concentrations (0.001 to 0.01 M) but little volume change in the range 0.025 to 0.36 M, closely paralleling results obtained with NaCl and KC1. Diamines (diaminopropane, -butane, -pentane, -hexane, -heptane, and -decane) produced shrinkage and granulation and nucleolar condensation in ≈ 0.025 M solutions and less shrinkage as the concentration of the diamines was increased. Condensation was readily reversed by either distilled water or the isolation medium. The effects of diamines resemble those of MgCl 2 and CaCl 2. Spermidine and spermine, which possess three and four positive charges, respectively, produce condensation at very low (0.001 M) concentrations, with marked swelling at approximately 0.2 M. Condensation was not reversed by distilled water and was slowly reversed by the phosphate-containing isolation medium. Chromosome-like structures were observed in a number of solutions but accurate counts were not possible. In a comparison of Amphiuma erythrocyte nuclei and rat liver nuclei, relatively few granules were seen in the former (2n = 24) whereas many were seen in liver nuclei (4n = 84), suggesting that the structures observed may be chromosomal in origin. Available evidence suggests that the prophase condensing agent contains more than two charges if condensation is caused only by charge effects.

The separation of aliphatic amines by paper chromatography or paper electrophoresis

Aliphatic monoamines, diamines, or polyamines have been separated by paper electrophoresis. The separation of a mixture of the bacterial growth factors putrescine, 1,3-propanediamine, spermidine, and spermine has been achieved by this same technique, while spermidine and spermine have also been separated and may be identified in tissue hydrolyzates by paper chromatographic and bioautographic procedures which are described.

The release of catechol amines from isolated chromaffin granules.

Release of catechol amines from the chromaffin granules of the bovine suprarenal medulla has been studied. Aliphatic monoamines and diamines released catechol amines from chromaffin granules under conditions similar to those under which they are known to promote the release of histamine from suspensions of granules. Carbachol and histamine did not release catechol amines from granules.

Metallic Complexes with the Aliphatic Poly-Amines

The existence of complex compounds of metallic salts with ammonia was recognised in the early years of last century. Platinum in particular readily unites with ammonia, and the early chemists, when studying the general chemistry of ammonium platino-and platini-chlorides, soon discovered highly crystalline ammonia derivatives of platinum which contained an unusually high proportion of the metal. In the formulation of such compounds difficulties at once arose. Thus Peyrone in 1844 knew three distinct compounds of the composition PtCl2N2H6, a pale lemoncoloured compound known as the second chloride of Reiset, an orange-coloured compound discovered by Peyrone himself, and finally a dark green insoluble substance known as Magnus' green salt, discovered by the latter in 1828. The existence of these three compounds, now known as trans and cis dichloro-diaminoplatinum [Pt(NH3)2Cl2], and as tetramino-platinous platinochloride [Pt(NH3)4]PtCl4 respectively, could not be satisfactorily explained on current theories of salt formation. Similar compounds in which aliphatic and cyclic mono-amines replaced the ammonia groups were discovered later, but it was not until 1889 that Jörgensen introduced the use of the simplest stable aliphatic diamine, viz. ethylene diamine.