Monoaminodicarboxylic Acids Research Articles

Amino acid composition of pollen <i>Pinus sylvestris</i> L. and <i>Pinus sibirica</i> Du Tour growing in the Baikal region

The purpose of the study was to determine the qualitative and quantitative amino acid composition of pollen Pinus sylvestris L. and Pinus sibirica Du Tour. Pine pollen was collected in June 2021 at natural sites on the southeastern coast of Lake Baikal. The mass fraction of crude protein was determined by the Kjeldahl method; the protein composition and individual amino acid content were determined by high-performance liquid chromatography with post-column modification of ninhydrin on an LA8080 automatic analyser (Hitachi, Japan). The crude protein content of the pollen was 14.38–15.94%. Pine pollen protein is shown to contain 17 amino acids, including 9 essential amino acids: valine, isoleucine, leucine, threonine, methionine, phenylalanine, lysine, histidine, and arginine. The content of the sum of amino acids was 141.4–156.5 mg/g, including essential amino acids 45.9-48.4%. The following amino acids are dominant in Pinus sylvestris and Pinus sibirica pollens (mg/g): monoaminodicarboxylic acids – glutamic (21.3–24.2) and aspartic (13.0–14.2), diaminocarboxylic acid arginine (17.0–17.4) and heterocyclic amino acid proline (14.7–16.2). The obtained results can be useful in the development of drugs and biologically active additives based on pollen Pinus sylvestris and Pinus sibirica, which, due to the presence of the above amino acids, have a nootropic, immunomodulatory, cardiac stimulating, and detoxifying effect.

Phosphonic Aminocarboxylic Acids

Methods of synthesis of phosphonic aminocarboxylic acids, ω-phosphonic analogs of monoaminodicarboxylic acids, are reviewed. Many of such compounds are ligands of ionotropic and metabotropic glutamate receptors determining the phenomenon of information processing and communication in central nervous system, important in view of prevention and treatment of Alzheimer, Huntington, and Parkinson diseases and other socially important neurodegenerative and psychoneurological diseases as well as learning and memory processes.

Changes in metabolic rate and N excretion in the marine invertebrate Sipunculus nudus under conditions of environmental hypercapnia: identifying effective acid-base variables.

Increased CO(2) partial pressures (hypercapnia) as well as hypoxia are natural features of marine environments like the intertidal zone. Nevertheless little is known about the specific effects of CO(2) on metabolism, except for the well-described effects on acid-base variables and regulation. Accordingly, the sediment-dwelling worm Sipunculus nudus was used as an experimental model to investigate the correlation of acid-base-induced metabolic depression and protein/amino acid catabolism, by determining the rates of oxygen consumption, ammonia excretion and O/N ratios in non-perfused preparations of body wall musculature at various levels of extra- and intracellular pH, P(CO(2)) and [HCO(3)(-)]. A decrease in extracellular pH from control level (7.9) to 6.7 caused a reduction in aerobic metabolic rate of both normocapnic and hypercapnic tissues by 40-45 %. O/N ratios of 4.0-4.5 under control conditions indicate that amino acid catabolism meets the largest fraction of aerobic energy demand. A significant 10-15 % drop in ammonia excretion, a simultaneous reduction of O/N ratios and a transient accumulation of intracellular bicarbonate during transition to extreme acidosis suggest a reduction in net amino acid catabolism and a shift in the selection of amino acids used, favouring monoamino dicarboxylic acids and their amines (asparagine, glutamine, aspartic and glutamic acids). A drop in intracellular pH was identified as mediating this effect. In conclusion, the present data provide evidence for a regulatory role of intracellular pH in the selection of amino acids used by catabolism.

Side reactions of monoaminodicarboxylic acids in peptide synthesis

N‐benzyloxycarbonyl‐l‐homoglutamine was studied to answer the question whether or not there is any tendency for the dehydration of the δ‐carboxamide group during activation and coupling. Only a minor conversion to nitrile by‐products was found in the activation of the α‐carboxyl group and formation of peptide bond with the help of dicyclohexylcarbodiimide. Addition of N‐hydroxybenzotriazole to the reacting mixture eliminates the side chain dehydration reaction. The dehydration reaction is also overcome by protection of the side chain carboxamide with the benzyloxycarbonylcarbamoyl substituent.

Prediction of stability constants. II. Metal chelates of natural alkyl amino acids and their synthetic analogs

The currently available critical stability constants of amino acid complexes of metal ions are employed as the basis for estimating the constants that have not been measured so as to provide a comprehensive data base describing the reactions of metal ions with twenty two types of aliphatic amino acid ligands. The latter include diaminomonocarboxylic and monoaminodicarboxylic acids, but are restricted to aliphatic naturally occurring ligands, and closely related synthetic compounds. In addition stability data are presented for fourteen structural types of monoprotonated amino acids, and six structural types of diprotonated amino acids. For more limited numbers of amino acid types data are presented and trends are discussed for the alkaline earths, the lanthanides, and the first row transition metal series. The need for more measured (experimental) data for the development of a comprehensive data base of measured and estimated constants for such groups of metal ions as the lanthanides, transition metals, the actinides, and a few heavy metal ions is pointed out.

Effect of Adsorption by Cellulose Acetate Membrane on Reverse Osmosis of Some Monoamino Monocarboxylic and Monoamino Dicarboxylic Acids in Aqueous Solutions

Abstract Taft’s polar and steric parameters, Σσ*, ΣEs, and nonpolar parameter, ΣS* governing the reverse osmosis of nonionized polar aliphatic and alicyclic organic compounds using a cellulose acetate membrane were also applicable to aliphatic monoamino monocarboxylic acids having zwitter ion structure. These three parameters were further extended so as to include the cases of sulfur-containing amino acids, hydroxy-substituted, and aromatic type amino acids. Reverse osmosis of monoamino monocarboxylic acids in binary aqueous solution systems containing l-alanine was carried out. As a result, added amino acids were adsorbed by the membrane when added in low concentration (<0.001 mol dm−3), and the permeation of l-alanine was governed by the difference of Taft’s polar parameter between l-alanine and the added amino acid. Reverse osmosis of monoamino dicarboxylic acids indicated that hydrogen ions were adsorbed by the membrane, and the adsorption isotherms of hydrogen ions were approximately represented by the Langmuir formula for each amino acid. The electrostatic repulsion between R− ionic species in monoamino dicarboxylic acid and the negatively dissociated groups of the membrane was weakened by neutralization of the membrane by hydrogen ion adsorption, resulting in decreased amino acid rejection. It was noted that the ultraviolet spectrum and the titration curve of permeate of amino acids were different from those of the feed solution; relationship between this phenomenon and adsorption of hydrogen ions was investigated.

Reverse osmosis treatment of some mixtures of monoamino monocarboxylic and monoamino dicarboxylic acids in aqueous solutions using cellulose acetate membrane.

Reverse osmosis treatment of some mixtures of monoamino monocarboxylic and monoamino dicarboxylic acids in aqueous solutions using cellulose acetate membrane.

Extraction, Assay and Conversion of NH. A Preparative Procedure for Isotopic Enrichment Determination

AbstractA method is described for the extraction of NH4+ from biological samples. This method can be combined with the enzymatic conversion of NH4+ to glutamate, which can then be used for measuring 15N isotopic enrichment. Emphasis is laid on the difficulties encountered when the samples contain NH4+ together with the amide derivative of monoaminodicarboxylic acids.

Metabolic traits in mentally retarded children as compared with normal populations: monoaminodicarboxylic acids and their half amides and total amino acids.

Journal of Intellectual Disability ResearchVolume 13, Issue 2 p. 130-142 METABOLIC TRAITS IN MENTALLY RETARDED CHILDREN AS COMPARED WITH NORMAL POPULATIONS: MONOAMINODICARBOXYLIC ACIDS AND THEIR HALF AMIDES AND TOTAL AMINO ACIDS W. HIRSCH, W. HIRSCH Paediatric Department, The Free University of Berlin and Institute of Anthropology and Human Genetics, University of Heidelberg Universitäts-Kinderklinik der Freien Universität Berlin, 1 Berlin 19, Heubnerweg 6, Germany.Search for more papers by this authorANNEMARIE MEX, ANNEMARIE MEX Paediatric Department, The Free University of Berlin and Institute of Anthropology and Human Genetics, University of Heidelberg 1 Berlin 45, Kadettenweg 39, Germany.Search for more papers by this authorF. VOGEL, F. VOGEL Paediatric Department, The Free University of Berlin and Institute of Anthropology and Human Genetics, University of Heidelberg Institut Für Anthropologie und Humangenetilt der Universität Heidelberg, Mönchhofstr. 15A, Germany.Search for more papers by this author W. HIRSCH, W. HIRSCH Paediatric Department, The Free University of Berlin and Institute of Anthropology and Human Genetics, University of Heidelberg Universitäts-Kinderklinik der Freien Universität Berlin, 1 Berlin 19, Heubnerweg 6, Germany.Search for more papers by this authorANNEMARIE MEX, ANNEMARIE MEX Paediatric Department, The Free University of Berlin and Institute of Anthropology and Human Genetics, University of Heidelberg 1 Berlin 45, Kadettenweg 39, Germany.Search for more papers by this authorF. VOGEL, F. VOGEL Paediatric Department, The Free University of Berlin and Institute of Anthropology and Human Genetics, University of Heidelberg Institut Für Anthropologie und Humangenetilt der Universität Heidelberg, Mönchhofstr. 15A, Germany.Search for more papers by this author First published: June 1969 https://doi.org/10.1111/j.1365-2788.1969.tb01073.x AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Volume13, Issue2June 1969Pages 130-142 RelatedInformation

クコの成分に関する研究(第4報)

クコ葉の水溶性抽出物が一定の培養条件下で乳酸菌に対して著しい生酸促進効果をもつことを認めたことから,これがクコ葉のいかなる成分によるかについて実験を行ない,つぎの結果を得た. (1) クコ葉の水溶性抽出物をpH 9またはpH 2においてブタノールあるいは酢酸エチルによる抽出を行なったところ,有機溶媒層よりも抽出残液の方がよりLact. acidophilusに対する生酸促進性を示した,このことから,クコ葉のLact. acidophilusに対する有効成分は両性物質であることが推定される. (2) クコ葉の水溶性抽出物をAmberlite IR-120およびIR-410を用いて分画し,これらのLact. acidophilusに対する生酸促進性をしらべた結果,両性物質区分は促進性を示したが,塩基,有機酸および中性成分の各区分はほとんど促進を示さなかった. (3) Amberlite IR-4BおよびIRG-50で処理して吸着物質を酸性,塩基性および中性の3区分に分けたのち,Lact.acidaphilusに対する生酸促進性をしらべたところ,とくに中性および塩基性区分に促進性があった.このことはLact. acidophilusに対する有効成分は単一物質ではないことを示している. (4) Amberlite IR-120によるクコ葉の水溶性抽出分画成分についてLact. acidophilusに有効な区分はLact. bulgaricus, Lact. caseiおよびStr. faecalisに対しても生酸促進性を示した.

クコの成分に関する研究(第5報)

Non protein nitrogenous substances in the aqueous extract of KUKO leaves were fractionated by means of column chromatography on ion exchange resin, zone electro-phoresis and cellulose column chromatography. The presence of active principles responsi-ble for acid formation of lactic acid bacteria under a certain condition was examined in each fraction. Twenty two amino acids including a-aminoadipic acid, α-aminopimelic acid, ethanol-amine, and β-alanine were detected. A mixture of these amino acids showed marked influence on acid formation of lactic acid bacteria, but any single amino acid was less effective in the stimulation of growth as compared with the mixture of amino acids. In a homologous series of monoamino dicarboxylic acids the acid formation was stimulated with the increase in the length of carbon chain. Adenine, guanine, xanthine, adenosine and an unidentified nucleotide were detected and these nucleic acid derivatives stimulated the acid formation by lactic acid bacteria.

Preparation and properties of γ-methyleneglutamic acid

Procedures are described for the preparation of dl-γ-methylene glutamic acid, d-γ-methyleneglutamic acid, N-acetyl- dl-γ-methyleneglutamic acid, and γ-amino-α-methylenebutyric acid. A new method for determining γ-methyleneglutamic acid is described. The method involves heating with concentrated hydroxylamine and does not yield appreciable color with other monoaminodicarboxylic acids. Glutamine synthetase preparations from peanut cotyledons and liver glutamic dehydrogenase do not catalyze their respective reactions with γ-methyleneglutamate. Preliminary evidence suggests that peanut extracts catalyze a glutamic dehydrogenase type reaction with γ-methylene glutamate.

Physical, physicochemical and chemical characteristics of macroglobulinic serum mucoprotein

Macroglobulinic and normal mucoprotein were isolated and purified from blood serum. The physical and physicochemical properties of both compounds were similar, but the isoelectric point was higher in the macroglobulinic mucoprotein. The molecular weight of both compounds was determined by sedimentation, diffusion and lightscattering methods: values of from 41,000 to 47,000 were calculated. Large differences in the content of sugars and aminated sugars were found. The number of residues of monoaminodicarboxylic acids is higher in macroglobulinic mucoprotein than in the normal compound.

Chemical excitation of spinal neurones.

THE presence of comparatively large quantities of glutamic acid in brain together with the conflicting evidence of the effects of glutamic acid administration1 have led to an investigation of the effects of this and related monoamino-dicarboxylic acids upon spinal cells. When applied ionophoretically, both glutamic and aspartic acids were very effective in evoking repetitive discharges from all types of inter-neurones located in the dorsal horn and intermediate nucleus of the spinal cord of the cat. For example, Fig. 1A illustrates the spike potentials of a dorsal horn cell activated orthodromically and recorded by means of one barrel of a double-barrelled electrode. The background discharge-rate of this cell was zero (Fig. 1B). Several seconds after a current of 120 mμ, amp. was employed to pass anion from a saturated solution of the sodium salt of L-glutamic acid (pH 8.5) in the other barrel of the electrode, the cell fired with a frequency of 100 per sec. (Fig. 1C), and 5 sec. later this had risen to 440 per sec. (Fig. 1D). 1 sec. after the current was stopped, the cell ceased firing. Control experiments indicated that this excitatory action was due specifically to the amino-acids and not to other effects arising from the passage of the ionophoretic currents.

Hydrazinolysis of Peptides and Proteins. II. Fundamental Studies on the Determination of the Carboxyl-ends of Proteins

Abstract 1. Fundamental experiments on the hydrazinolysis method, a method for characterization of C-terminal amino acids of proteins, were carried out. 2. Amino acids were found to decompose to various extents by heating with anhydrous hydrazine. 3. Amino acid hydrazides were hydrolysed about 1% or less by heating with anhydrous hydrazine (ca. 99%) for ten hours. Hydrolyses of them in neutral and slightly acidic solutions at room temperature are negligible, but in alkaline solution the extent of hydrolyses are somewhat greater though less than 0.2% in five hours in 1% bicarbonate solution. 4. Procedures for separating free amino acids from amino acid hydrazides as DNP-derivatives with or without treatment of iso-valeraldehyde prior to dinitrophenylation were reinvestigated thoroughly. 5. Some experiments on the hydrazino-lyses of peptides were done. 6. Fundamental investigations of the characterization of the mode of linkage of monoaminodicarboxylic acids in peptide chains by the hydrazinolysis method indicate its availability. 7. Standard methods for quantitative estimation of C-terminal amino acids or proteins are established based upon the results obtained by the present investigation. 8. Brief consideration on the mechanism of the hydrazinolysis was described and the scope of this method was discussed in conection with that of the carboxypeptidase method