cas 462-94-2, 1,5-Diaminopentane | Articles data

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The use of l-lysine decarboxylase as a means to separate amino acids by electrodialysis
Amino acids (AA's) are interesting materials as feedstocks for the chemical industry as they contain chemical functionalities similar to conventional petrochemicals. This offers the possibility to circumvent process steps, energy and reagents. AA's can be obtained by the hydrolysis of potentially inexpensive voluminous protein streams derived from biofuel production. However, isolation of the preferred AA is required in order to carry out further transformation into the desired product. Theoretically separation may be achieved using electrodialysis. To increase efficiency, specific modification to a product of industrial interest and removes charged groups of AA's with similar isoelectric points is required. Here, the reaction of l-lysine decarboxylase (LDC) was studied as a means to specifically convert l-lysine (Lys) to 1,5-pentanediamine (PDA) in the presence of l-arginine (Arg) to produce products with different charge thus allowing isolation of products by electrodialysis. Immobilization of LDC in calcium alginate enhanced the operational stability and conversion in mixtures of amino acids was highly specific. At 30 °C the presence of Arg had little effect on the activity of the enzyme although inhibition by the product PDA could be observed. Volumetric productivity was calculated and raw material and transformation costs were estimated for a potential process using a mixture of Arg and Lys. The Royal Society of Chemistry.
Teng, Yinglai,Scott, Elinor L.,Van Zeeland, Albert N. T.,Sanders, Johan P. M.
p. 624 - 630
(2011)
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Stoffwechselprodukte von Mikroorganismen. 216 Mitteilung. Isolierung, Strukturaufklaerung und Synthese von Ferrioxamin H
The structure of ferrioxamine H, a minor component of the sideramine complex of actinomycetes, was determined by spectroscopic investigations, degradation and synthesis.Ferrioxamine H is the Fe(III)-complex of 11,22-dihydroxy-4,12,15,23-tetraoxo-5,11,16,22-tetraazatetracosanoic acid (2).
Adapa, Srinivas,Huber, Peter,Keller-Schierlein, Walter
p. 1818 - 1824
(1982)
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Advances in bio-nylon 5X: Discovery of new lysine decarboxylases for the high-level production of cadaverine
Cadaverine (1,5-pentanediamine) is the most important precursor for nylon PA5X, which has an extremely competitive market due to the high consumption of engineered plastics and fibers. The key enzyme lysine decarboxylase is in desperate need for industrial bio-based cadaverine production. In this study, new lysine decarboxylases have been mined by peptide pattern recognition for the high-level production of cadaverine. The predicted enzymes were expressed in E. coli and analyzed as whole-cell biocatalysts. Two outstanding recombinant enzymes from Edwardsiella tarda and Aeromonas sp. (LdcEt and LdcAer, respectively), were further purified and characterized. The optimal pH and temperature for LdcEt and LdcAer were pH 7, 55 °C and pH 6, 50 °C, respectively. These two enzymes were stable over the pH range of 5-7 during 24 h incubation. Both of them still had activity after being incubated at pH 8. LdcEt and LdcAer also have good thermostability with a half-life of 14.5 h and 20.3 h at 60 °C, respectively. The kinetic analysis showed that they have high catalytic efficiency as the kcat/Km (LdcEt: 243.28 s-1 mM-1; LdcAer: 266.86 s-1 mM-1) was the highest when compared for all the related studies. The whole cell conversion by LdcEt with 0.1% (v/v) Triton X-100 can convert 100% 2 M l-lysine HCl to cadaverine in 2 h and the cadaverine productivity was high up to 103.47 ± 4.37 g L-1 h-1. The in vitro studies further found that unpurified cell-lysates of LdcEt had relatively higher activity compared to the whole cell conversion. Meanwhile, 0.4 mg mL-1 purified LdcEt and LdcAer can efficiently produce 165.96 ± 1.41 g L-1 and 155.84 ± 4.63 g L-1 cadaverine only in 0.5 h, respectively. The high specific activity, pH, thermo-stability, and catalytic efficiency in vivo and in vitro, combined with simultaneous cell treatment with Triton X-100 and the bioconversion process, provide LdcEt with great potential in the economic and efficient production of cadaverine at the industrial scale. This journal is
Xue, Yaju,Zhao, Yongliang,Ji, Xiuling,Yao, Jiahao,Busk, Peter Kamp,Lange, Lene,Huang, Yuhong,Zhang, Suojiang
p. 8656 - 8668
(2020)
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Engineering a cleavable disulfide bond into a natural product siderophore using precursor-directed biosynthesis
An analogue of the bacterial siderophore desferrioxamine B (DFOB) containing a disulfide motif in the backbone was produced from Streptomyces pilosus cultures supplemented with cystamine. Cystamine competed against native 1,5-diaminopentane during assembly. DFOB-(SS)1[001] and its complexes with Fe(iii) or Ga(iii) were cleaved upon incubation with dithiothreitol. Compounds such as DFOB-(SS)1[001] and its thiol-containing cleavage products could expand antibiotic strategies and Au-S-based nanotechnologies.
Richardson-Sanchez, Tomas,Codd, Rachel
p. 9813 - 9816
(2018)
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Supramolecular Assays for Mapping Enzyme Activity by Displacement-Triggered Change in Hyperpolarized 129Xe Magnetization Transfer NMR Spectroscopy
Reversibly bound Xe is a sensitive NMR and MRI reporter with its resonance frequency being influenced by the chemical environment of the host. Molecular imaging of enzyme activity presents a promising approach for disease identification, but current Xe biosensing concepts are limited since substrate conversion typically has little impact on the chemical shift of Xe inside tailored cavities. Herein, we exploit the ability of the product of the enzymatic reaction to bind itself to the macrocyclic hosts CB6 and CB7 and thereby displace Xe. We demonstrate the suitability of this method to map areas of enzyme activity through changes in magnetization transfer with hyperpolarized Xe under different saturation scenarios. The supramolecular recognition properties of cucurbiturils are exploited in a modified signal-transfer approach in Xe NMR spectroscopy. Magnetic resonance imaging of enzymatic reactions was possible in this way by displacement of hyperpolarized 129Xe.
Schnurr, Matthias,Sloniec-Myszk, Jagoda,D?pfert, J?rg,Schr?der, Leif,Hennig, Andreas
p. 13444 - 13447
(2015)
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The Effect of Visible Light on the Catalytic Activity of PLP-Dependent Enzymes
Pyridoxal 5’-phosphate (PLP)-dependent enzymes are a versatile class of biocatalysts and feature a variety of industrial applications. However, PLP is light sensitive and can cause inactivation of enzymes in certain light conditions. As most of the PLP-dependent enzymes are usually not handled in dark conditions, we evaluated the effect of visible light on the activity of PLP-dependent enzymes during production as well as transformation. We tested four amine transaminases, from Chromobacterium violaceum, Bacillus megaterium, Vibrio fluvialis and a variant from Arthrobacter species as well as two lysine decarboxylases, from Selenomonas ruminantium and the LDCc from Escherichia coli. It appeared that five of these six enzymes suffered from a significant decrease in activity by up to 90 % when handled in laboratory light conditions. Surprisingly, only the amine transaminase variant from Arthrobacter species appeared to be unaffected by light exposure and even showed an activation to 150 % relative activity over the course of 6 h regardless of the light conditions.
Gerlach, Tim,Nugroho, David Limanhadi,Rother, D?rte
p. 2398 - 2406
(2021/04/05)

Preparation method of pentamethylene diamine
The invention provides a preparation method of pentamethylene diamine. The method comprises the following steps: a) reacting acrylonitrile with acetaldehyde under the catalytic action of N,N-dihydroxyethyl-1,4-pentamethylene diamine to obtain 5-formyl valeronitrile; and b) carrying out one-step reaction on the product obtained in the step a) and mixed gas of ammonia gas and hydrogen under the action of a catalyst and an auxiliary agent to obtain pentamethylene diamine. Compared with the traditional method for synthesizing pentamethylene diamine by using lysine as a raw material and a biological method, the method has the advantages of simple steps and low cost, and is suitable for large-scale production of pentamethylene diamine. The use of the catalyst N,N-dihydroxyethyl-1,4-pentamethylene diamine can inhibit the self-polymerization of acetaldehyde and acrylonitrile, thereby greatly enhancing the selectivity of the target intermediate.
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Paragraph 0042; 0045; 0052-0057; 0064-0066

(2021/11/27)

MODIFIED MEMBRANE PERMEABILITY
Provided are microorganisms genetically modified to overexpress porin polypeptides to enhance the production of lysine and lysine derivatives by the microorganism. Also provided are methods of generating such microorganism, and methods of producing lysine and lysine derivatives using the genetically modified microorganisms.
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(2019/02/13)

Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
p. 4297 - 4306
(2019/08/26)

A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)
The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)
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(2018/04/03)

SNS-Ligands for Ru-Catalyzed Homogeneous Hydrogenation and Dehydrogenation Reactions
A detailed study of literature-known and novel S-containing pincer-type ligands for ruthenium-catalyzed homogeneous hydrogenation and dehydrogenation reactions was carried out. The scope and limitations of these catalysts were carefully investigated, and it was shown that simple bench-stable SNS-Ru complexes can be used to facilitate the hydrogenation of a variety of different substrates at a maximum H2 pressure of 20 bar under operationally simple, easy to scale up, glovebox-free conditions by using starting materials and reagents that do not require any special purification prior to use. It was also shown that such complexes can be used to catalyze the dehydrogenative coupling of alcohols and amines to get amides as well as for the dehydrogenative dimerization of alcohols to esters.
Sch?rgenhumer, Johannes,Zimmermann, Axel,Waser, Mario
supporting information
p. 862 - 870
(2018/06/18)

METHOD FOR PRODUCING PENTAMETHYLENE DIISOCYANATE
PROBLEM TO BE SOLVED: To provide a method for producing pentamethylene diisocyanate which can suppress decrease in flowability of a salt-forming mixture containing pentamethylenediamine hydrochloride in a salt-forming step and suppress adhesion of pentamethylenediamine hydrochloride to a stirring vessel. SOLUTION: There is obtained pentamethylene diisocyanate by preparing an amine raw material containing pentamethylenediamine in which the content ratio of ethanolamine is 0.10 mass% or less, mixing the amine raw material and hydrogen chloride to obtain pentamethylenediamine hydrochloride, followed by reacting the pentamethylenediamine hydrochloride and carbonyl chloride. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT
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(2018/08/22)

A method of manufacturing an alkylene polyamine
PROBLEM TO BE SOLVED: To provide a method for producing an alkylene polyamine economically with high productivity, and, in particular, to provide a method for producing an alkylene polyamine from an amino acid having an aminoalkyl group such as lysin or ornithine.SOLUTION: There is provided a method for producing an amine compound in which an amino acid having an aminoalkyl group is subjected to decarboxylation reaction at a reaction temperature of 160 to 300°C in the presence of a cyclic ketone which is a liquid state at 160 to 300°C (in terms of atmospheric pressure).
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(2017/08/02)

Method for Producing 1,5-Pentanediamine
A simple and efficient method for producing 1,5-pentanediamine in a free form is provided. The method for producing 1,5-pentanediamine in a free form from a salt of 1,5-pentanediamine includes a step of adsorbing 1,5-pentanediamine in a free form onto a column of an ion exchange resin by applying a solution of salt of 1,5-pentanediamine to the column of the ion exchange resin, and a step of eluting a solution of the 1,5-pentanediamine in a free form from the ion exchange resin by applying an eluent solution to the column of the ion exchange resin onto which the 1,5-pentanediamine in a free form is absorbed.
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(2016/07/05)

METHOD FOR PRODUCING ALKANOL AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
PROBLEM TO BE SOLVED: To provide a method for producing alkanol amines by alcohol amination of diols using ammonia under elimination of water. SOLUTION: The invention relates to a method for producing alkanol amines which comprise a primary amino group (-NH2) and a hydroxyl group (-OH), by alcohol amination of diols comprising two hydroxyl groups (-OH) using ammonia under elimination of water. The reaction is homogeneously catalyzed in the presence of at least one complex catalyst which contains at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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(2016/10/27)

Production of amine compound (by machine translation)
PROBLEM TO BE SOLVED: To provide an industrially suitable method of producing an amine compound.SOLUTION: A method of producing an amine compound uses a specified imine compound as a reaction catalyst and is based on a decarboxylation reaction of an amino acid compound which has at least one amino group optionally having a substituent and at least one carboxyl group optionally having a substituent. The method is especially characterized by the decarboxylation reaction using an amino acid or its derivative as a production raw material.
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(2017/05/23)

Applications of dynamic combinatorial chemistry for the determination of effective molarity
A new strategy for determining thermodynamic effective molarities (EM) for macrocylisation reactions using dynamic combinatorial chemistry under dilute conditions is presented. At low concentrations, below the critical value, Dynamic Libraries (DLs) of bifunctional building blocks contain only cyclic species, so it is not possible to quantify the equilibria between linear and cyclic species. However, addition of a monofunctional chain stopper can be used to promote the formation of linear oligomers allowing measurement of EM for all cyclic species present in the DL. The effectiveness of this approach was demonstrated for DLs generated from mixtures of 1,3-diimine calix[4]arenes, linear diaminoalkanes and monoaminoalkanes. For macrocycles deriving from one bifunctional calixarene and one diamine, there is an alternating pattern of EM values with the number of methylene units in the diamine: odd numbers give significantly higher EMs than even numbers. For odd numbers of methylene units, the alkyl chain can adopt an extended all anti conformation, whereas for even numbers of methylene units, gauche conformations are required for cyclisation, and the associated strain reduces EM. The value of EM for the five-carbon linker indicates that this macrocycle is a strainless ring. This journal is
Ciaccia, Maria,Tosi, Irene,Baldini, Laura,Cacciapaglia, Roberta,Mandolini, Luigi,Di Stefano, Stefano,Hunter, Christopher A.
p. 144 - 151
(2015/02/19)

· Uniform catalyst by using alcohol aminosilicone di-, tri-and a method of manufacturing a polyphenylenepolyamine
The invention relates to a method for producing primary amines, which contain at least one functional group of the formula (-CH2-NH2) and at least one further primary amino group, by the alcohol amination of reactants, which contain at least one functional group of the formula (-CH2-OH) and at least one further functional group (-X), wherein (-X) is selected from hydroxyl groups and primary amino groups, using ammonia with removal of water, wherein the reaction is carried out in a homogeneously catalyzed manner in the presence of at least one complex catalyst containing at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand.
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Paragraph 0099; 0113

(2016/10/09)

PENTAMETHYLENE DIISOCYANATE, METHOD FOR PRODUCING PENTAMETHYLENE DIISOCYANATE, POLYISOCYANATE COMPOSITION, POLYURETHANE RESIN, AND POLYUREA RESIN
A Pentamethylene diisocyanate is obtained by phosgenating pentamethylenediamine or its salt obtained by a biochemical method, and contains 5 to 400 ppm of a compound represented by the general formula (1) below and a compound represented by the general formula (2) below in total:
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Paragraph 0541

(2014/01/23)

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels
Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.
Yang, Donglai,Arifhodzic, Lejla,Ganellin, C. Robin,Jenkinson, Donald H.
supporting information
p. 907 - 923
(2013/07/27)

METHOD FOR PURIFYING COMPOUNDS CONTAINING AMINO GROUPS
Method for purifying compounds (I) containing amino groups from a polar phase A, where (I) is converted by reaction with an aldehyde or ketone (II) into the corresponding imine (III) which is insoluble or sparingly soluble in the polar phase A, andthen the imine (III) is converted to a nonpolar phase B andseparated off from phase A, and then the compound containing amino groups is recovered from the imine (III).
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Page/Page column 4

(2012/10/08)

Solid phase synthesis of cadaverine on polymer support
Cadaverine is a naturally occurring polyamine which is closely associated with spermine and spermidine, two major polyamines which regulate growth processes in living beings. Using polystyrene as solid support and with the help of a photocleavable linker, cadaverine was synthesised. The only purification process involved throughout the synthesis is filtration and washing with suitable solvents. Cadaverine was first synthesised over polystyrene support and then cleaved from matrix photolytically. The yield and purity of the sample was studied using differently cross linked polystyrene resin with divinyl benzene as the cross linking agent. The effect of one photocleavable linker was studied. The synthesis of linker was done by classical organic synthetic procedure.
Santhakumari
scheme or table
p. 3449 - 3453
(2012/07/31)

PROCESS FOR PREPARING ALKANOLAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
Process for preparing alkanolamines which have a primary amino group (—NH2) and a hydroxyl group (—OH) by alcohol amination of diols having two hydroxyl groups (—OH) by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
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Page/Page column 13-14; 20

(2012/09/22)

PROCESS FOR PREPARING DI-, TRI- AND POLYAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
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Page/Page column 12; 16

(2012/09/22)

PROBIOTIC MICROORGANISMS FOR THE REDUCTION OF MANURE ODOR
Described are microorganism which are able to reduce the generation of feces odor by decreasing the amount of at least one of the compounds methyl mercaptan, a sulphide compound, cadavarine, putrescine, indole or skatole, and wherein said decrease in the amount of said compounds is independent of the growth of the microorganism. Also described are compositions, comprising such microorganisms, e.g. food, feed or pharmaceutical compositions and the use of such microorganisms for suppressing feces odor or the preparation of foodstuff or feedstuff, as well as corresponding methods for the production of food or feed composition and additives for food, feed or drinks.
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(2011/06/10)

Analysis of catalytic determinants of diaminopimelate and ornithine decarboxylases using alternate substrates
Diaminopimelate decarboxylase (DAPDC) and ornithine decarboxylase (ODC) are pyridoxal 5′-phosphate dependent enzymes that are critical to microbial growth and pathogenicity. The latter is the target of drugs that cure African sleeping sickness, while the former is an attractive target for antibacterials. These two enzymes share the (β/α)8 (i.e., TIM barrel) fold with alanine racemase, another pyridoxal 5′-phosphate dependent enzyme critical to bacterial survival. The active site structural homology between DAPDC and ODC is striking even though DAPDC catalyzes the decarboxylation of a D stereocenter with inversion of configuration and ODC catalyzes the decarboxylation of an L stereocenter with retention of configuration. Here, the structural and mechanistic bases of these interesting properties are explored using reactions of alternate substrates with both enzymes. It is concluded that simple binding determinants do not control the observed stereochemical specificities for decarboxylation, and a concerted decarboxylation/proton transfer at Cα of the D stereocenter of diaminopimelate is a possible mechanism for the observed specificity with DAPDC.
Fogle, Emily J.,Toney, Michael D.
experimental part
p. 1113 - 1119
(2012/06/04)

PROCESS FOR PRODUCING DIAMINE AND POLYAMIDE
By a method for producing a diamine comprising the step of purifying a diamine from an aqueous solution containing a diamine salt, the method comprising a step of adding an alkaline substance to the aqueous solution and then filtering the resulting solution by allowing the solution to pass through a nanofiltration membrane to remove the salt, thereby obtaining an aqueous diamine solution, a diamine suitable as a raw material for a polyamide can be obtained by a simpler operation than by a conventional extraction operation with an organic solvent.
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Page/Page column 12-13

(2011/01/11)

Novel agonists and antagonists for human protease activated receptor 2
Human protease activated receptor 2 (PAR2) is a G protein-coupled receptor that is associated with inflammatory diseases and cancers. PAR2 is activated by serine proteases that cleave its N-terminus and by synthetic peptides corresponding to the new N-terminus. Peptide agonists are widely used to characterize physiological roles for PAR2 but typically have low potency (e.g., SLIGKV-NH2, SLIGRL-NH2), uncertain target selectivity, and poor bioavailability, limiting their usefulness for specifically interrogating PAR2 in vivo. Structure-activity relationships were used to derive new PAR2 agonists and antagonists containing nonpeptidic moieties. Agonist GB110 (19, EC50 0.28 μM) selectively induced PAR2-, but not PAR1-, mediated intracellular Ca2+ release in HT29 human colorectal carcinoma cells. Antagonist GB83 (36, IC50 2 μM) is the first compound at micromolar concentrations to reversibly inhibit PAR2 activation by both proteases and other PAR2 agonists (e.g., trypsin, 2f-furoyl-LIGRLO-NH 2, 19). The new compounds are selective for PAR2 over PAR1, serum stable, and suitable for modulating PAR2 in disease models.
Barry, Grant D.,Suen, Jacky Y.,Le, Giang T.,Cotterell, Adam,Reid, Robert C.,Fairlie, David P.
experimental part
p. 7428 - 7440
(2011/02/23)

Substrate-selective supramolecular tandem assays: Monitoring enzyme inhibition of arginase and diamine oxidase by fluorescent dye displacement from calixarene and cucurbituril macrocycles
A combination of moderately selective host-guest binding with the impressive specificity of enzymatic transformations allows the real-time monitoring of enzymatic reactions in a homogeneous solution. The resulting enzyme assays ("supramolecular tandem assays") exploit the dynamic binding of a fluorescent dye with a macrocyclic host in competition with the binding of the substrate and product. Two examples of enzymatic reactions were investigated: the hydrolysis of arginine to ornithine catalyzed by arginase and the oxidation of cadaverine to 5-aminopentanal by diamine oxidase, in which the substrates have a higher affinity to the macrocycle than the products ("substrate-selective assays"). The depletion of the substrate allows the fluorescent dye to enter the macrocycle in the course of the enzymatic reaction, which leads to the desired fluorescence response. For arginase, p-sulfonatocalix[4]arene was used as the macrocycle, which displayed binding constants of 6400 M-1 with arginine, 550 M-1 with ornithine, and 60 000 M-1 with the selected fluorescent dye (1-aminomethyl-2,3-diazabicyclo[2.2.2]oct-2-ene); the dye shows a weaker fluorescence in its complexed state, which leads to a switch-off fluorescence response in the course of the enzymatic reaction. For diamine oxidase, cucurbit[7]uril (CB7) was used as the macrocycle, which showed binding constants of 4.5 × 106 M-1 with cadaverine, 1.1 × 105 M-1 with 1-aminopentane (as a model for the thermally unstable 1-aminopentanal), and 2.9 × 105 M-1 with the selected fluorescent dye (acridine orange, AO); AO shows a stronger fluorescence in its complexed state, which leads to a switch-on fluorescence response upon enzymatic oxidation. It is demonstrated that tandem assays can be successfully used to probe the inhibition of enzymes. Inhibition constants were estimated for the addition of known inhibitors, i.e., S-(2-boronoethyl)-L- cysteine and 2(S)-amino-6-boronohexanoic acid for arginase and potassium cyanide for diamine oxidase. Through the sequential coupling of a "product- selective" with a "substrate-selective" assay it was furthermore possible to monitor a multistep biochemical pathway, namely the decarboxylation of lysine to cadaverine by lysine decarboxylase followed by the oxidation of cadaverine by diamine oxidase. This "domino tandem assay" was performed in the same solution with a single reporter pair (CB7/AO).
Nau, Werner M.,Ghale, Garima,Hennig, Andreas,Bakirci, Hueseyin,Bailey, David M.
body text
p. 11558 - 11570
(2011/03/21)

Functionalized Photoreactive Compounds
The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.
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(2008/12/08)

CONTINUOUS PROCESS FOR DECARBOXYLATING CARBOXYLIC ACIDS
A continuous process for decarboxylating carboxylic acids proceeds by I.) initially charging a carbonyl compound as a catalyst in a solvent at reaction temperature, to obtain a catalyst solution; II.) metering a carboxylic acid into the catalyst solution as an aqueous solution, aqueous suspension or as a water-comprising solid, to obtain a reaction mixture; and III.) continuously removing a mixture of CO2, solvent, water and a reaction product or mixture of reaction products from the reaction mixture as a vapor.
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(2008/12/08)

PROCESS FOR ISOLATION OF AN ORGANIC AMINE
The invention relates to a process for the isolation of an organic amine from a composition comprising the organic amine and an acid, or a salt of the organic amine and the acid, wherein the process comprises steps wherein ammonia or hydrazine is added to the composition thereby forming a multi-phase system comprising an organic amine -rich phase and an acid-rich phase, the organic amine-rich phase and the acid-rich phase obtained in step (i) are separated, and the organic amine is isolated from the organic amine -rich phase.
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(2008/06/13)

Fluorescent sensors for diamines
A series of seven diamine sensors was prepared using dimers of a quinolone aldehyde chromophore. Binding to six different diamine guests was explored by a combination of NMR, absorption and fluorescence spectroscopy. It was shown that the dimeric sensors bound the diamine guests by formation of a bis-iminium ion which produced large changes in the fluorescence of the quinolone core. Issues of selectivity between guests are discussed. The Royal Society of Chemistry 2005.
Secor, Kristen,Plante, Jeffrey,Avetta, Christopher,Glass, Timothy
p. 4073 - 4077
(2007/10/03)

One-pot sequence for the decarboxylation of α-amino acids
Treatment of an α-amino acid with N-bromosuccinimide in water at pH 5 or in an alcoholic-aqueous ammonium chloride mixture, followed by addition of nickel(II) chloride and sodium borohydride, effected an overall decarboxylation via an intermediate nitrile to afford the corresponding amine in good yield.
Laval, Gilles,Golding, Bernard T.
p. 542 - 546
(2007/10/03)

Novel characteristics of Selenomonas ruminantium lysine decarboxylase capable of decarboxylating both L-lysine and L-ornithine
Lysine decarboxylase (LDC; EC 4.1.1.18) of Selenomonas ruminantium is a constitutive enzyme and is involved in the synthesis of cadaverine, which is an essential constituent of the peptidoglycan for normal cell growth. We purified the 5. ruminantium LDC by an improved method including hydrophobic chromatography and studied the fine characteristics of the enzyme. Kinetic study of LDC showed that 5. ruminanitum LDC decarboxylated both L-lysine and L-ornithine with similar Km, and the decarboxylase activities towards both substrates were competitively and irreversibly inhibited by DL-α-difluoromethylornithine, which is a specific inhibitor of ornithine decarboxylase (EC 4.1.1.17). We also showed a drastic descent of LDC activity owing to the degradation of LDC at entry into the stationary phase of cell growth.
Takatsuka, Yumiko,Onoda, Motoko,Sugiyama, Takeyoshi,Muramoto, Koji,Tomita, Toshio,Kamio, Yoshiyuki
p. 1063 - 1069
(2007/10/03)

Decolorization of polyalkylene polyamines
A process for decolorizing polyalkylene polyamines, which comprises contacting one or more polyalkylene polyamines having an average molecular weight of greater than about 200 and less than about 1000 with carbon at a temperature greater than or equal to about 100° C. and less than or equal to about 300° C. under conditions effective to reduce the color rating of the one or more polyalkylene polyamines.
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(2008/06/13)

A NOVEL DECARBOXYLATION OF α-AMINO ACIDS. A FACILE METHOD OF DECARBOXYLATION BY THE USE OF 2-CYCLOHEXEN-1-ONE AS A CATALYST
In the presence of a catalytic amount of 2-cyclohexen-1-one, decarboxylation of α-amino acids proceeds smoothly and affords the corresponding amino compounds in good yields.Optically active amino compounds, (3R)-(-)-3-hydroxypyrrolidine and (2R)-(-)-2-hydroxypropylamine are obtained in 93percent and 80percent yields, respectively.
Hashimoto, Mitsunori,Eda, Yutaka,Osanai, Yasutomo,Iwai, Toshiaki,Aoki, Seiichi
p. 893 - 896
(2007/10/02)

Synthesis of Primary Amines via Alkylation of the Sodium Salt of Trifluoroacetamide: An Alternative to the Gabriel Synthesis
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Harland, Philip A.,Hodge, Philip,Maughan, Wilfrid,Wildsmith, Eric
p. 941 - 943
(2007/10/02)

Triazine derivatives
The invention relates to polymers of triazine compounds containing piperidine groups which may serve as low volatile and migration-resistant light stabilizers for synthetic polymers. They have the structure STR1 and are obtained from cyanuric halides, diamines and polyalkylpiperidylamino compounds.
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(2008/06/13)