- UNUSUAL NONPROTEIN IMINO ACID AND ITS RELATIONSHIP TO PHENOLIC AND NITROGENOUS COMPOUNDS IN COPAIFERA
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The unusual imino acid, N-methyl-trans-4-hydroxy-L-proline has been isolated from leaves of five species of the leguminous tropical tree Copaifera, and for the first time characterized by 1H and 13C NMR and mass spectrometry.This imino acid can constitute up to 3 percent of the mature leaf dry weight and 10 percent of the nitrogen; it also constitutes 2-3 percent of the dry weight of the seed.Preliminary feeding trials have shown it to be a very effective inhibitor of larval development of the seed-feeding bruchid beetle Callosobruchus maculatus and to have significant feeding deterrence of the leaf-feeding lepidopteran Spodoptera littoralis.Phenolic compounds, also known to effect herbivores adversely, comprise 6-10 percent leaf dry weight.However, the imino acid displayed a mean of 50 percent reactivity compared to standards commonly used in analysis of total phenolics by the Folin-Denis (F-D) assay , thus resulting in a significant overestimate of phenolics by this assay.It is concluded that assessment of leaf food quality for herivores of Copaifera by assays widely used for this purpose in ecological studies, such as F-D for phenolics and Kjeldahl for total nitrogen content, give some misleading results.Key Word Index - Copaifera species; Caesalpinioideae; leaf and seed nonprotein imino acid; N-methyl-trans-4-hydroxy-L-proline; 4-hydroxyhydric acid; 4-hydroxy-1-methylpyrrolidine-2-carboxylic acid; leaf phenolics; Folin-Denis reagent; Kjeldahl analysis.
- Figliuolo, Roberto,Naylor, Stephen,Wang, Jinliang,Langenheim, Jean H.
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- Nitrogenous ovipositional deterrents in the leaves of sweet pepper (Capsicum annuum) at the mature stage against the leafminer, Liriomyza trifolii (Burgess)
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Mature leaves of the sweet pepper, Capsicum annuum, exhibited resistance against the American serpentine leafminer, Liriomyza trifolii (Burgess), Agromyzidae. Based on bioassay-guided fractionation, three compounds, namely 4-aminobutanoic acid, (2S,4R)-4-hydroxy-1-methyl-2-pyrrolidine carboxylic acid and 4-amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinone, were isolated from the leaves of sweet pepper. These compounds had significant oviposition deterrence towards adult flies of L. trifolii from laying their eggs on host plant leaves treated at 3.70, 16.60 and 6.45 μg/cm2, respectively.
- Dekebo, Aman,Kashiwagi, Takehiro,Tebayashi, Shin-Ich,Kim, Chul-Sa
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- Detection of Peanut Adulteration in Food Samples by Nuclear Magnetic Resonance Spectroscopy
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The addition of cheap and also readily available raw materials, such as peanut powder, to visually and chemically similar matrices is a common problem in the food industry. When peanuts are used as an adulterant, there is an additional risk of potential health hazard to consumers as a result of allergy-induced anaphylaxis. In this study, different series of peanut admixtures to visually similar food products, such as powdered hazelnuts, almonds, and walnuts, were prepared and analyzed by 1H nuclear magnetic resonance (NMR) spectroscopy. For identification, an isolated signal at 3.05 ppm in the 1H NMR spectrum of polar peanut extract was used as an indicator of peanut adulteration. The chemical marker was identified as (2S,4R)-N-methyl-4-hydroxy-l-proline by resynthesis of the compound and used as an internal standard. The signal-to-noise ratio and the integral of the signal of the marker can both be used to detect peanut impurities. Overall, an approximate limit of detection of 4% admixtures of peanut in various food products was determined using a 400 MHz spectrometer. With regard to food fraud, we present a viable screening method for detection of economic-relevant peanut adulteration.
- Bastek, Tim,Fischer, Markus,Hackl, Thomas,Schmitt, Caroline,Schneider, Tobias,Stelzer, Alina
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- N-methyl-trans-4-hydroxy-L-proline crystal compound and preparing method thereof
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The invention discloses an N-methyl-trans-4-hydroxy-L-proline crystal compound and a preparing method thereof.Crystals are measured with a powder X-ray diffraction measuring method, and an X-ray powder diffraction pattern expressed with the diffraction angle of 2theta+/-2 degrees shows characteristic diffraction peaks at 13.0 degrees, 13.4 degrees, 13.9 degrees, 16.7 degrees, 12.6 degrees, 18.3 degrees, 20.3 degrees, 21.0 degrees, 21.6 degrees, 22.2 degrees, 23.0 degrees, 23.9 degrees, 25.5 degrees, 27.0 degrees, 28.0 degrees, 29.6 degrees, 30.7 degrees, 31.1 degrees, 32.3 degrees, 33.4 degrees, 34.4 degrees, 34.9 degrees, 35.2 degrees and 37.1 degrees.The target crystal product is obtained through the three steps of reductive amination methylation, adsorption filtering and recrystallization.Cost is low, and raw materials are easy to obtain; operation is easy and convenient, and the reaction cycle is short.
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Paragraph 0035; 0036; 0037; 0038; 0039; 0040
(2016/11/28)
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- HETEROCYCLYL LINKED IMIDAZOPYRIDAZINE DERIVATIVES AS PI3KBETA INHIBITORS
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The present invention relates to heterocyclyl linked imidazopyridazine derivatives of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PI3Kβ inhibitors. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.
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- 7-(Piperazine-1-Ymethyl)-1H-Indole-2-Carboxylic Acid (Phenyl)-Amide Derivatives and Allied Compounds as P38 Map Kinase Inhibitors for the Treatment of Respiratory Diseases
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The present invention provides compounds according to general formula (I) which are proposed for the treatment of respiratory complaints, particularly asthma and COPD.
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Page/Page column 44
(2011/11/12)
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- Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions
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We report a mild and environmentally benign method for the synthesis of tertiary amines using alcohols as the alkylating reagents. Not only secondary amines such as piperazines but also amino acids and amino alcohols can be N-alkylated selectively. For N,O-benzyl protected amino alcohols, both N,O-de-benzylation and N-methylation were achieved in one-pot. The Royal Society of Chemistry.
- Xu, Chu-Pei,Xiao, Zhen-Hua,Zhuo, Bi-Qin,Wang, Yu-Huang,Huang, Pei-Qiang
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supporting information; experimental part
p. 7834 - 7836
(2010/11/24)
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- PROLINE DERIVATIVES USED AS PHARMACEUTICAL ACTIVE INGREDIENTS FOR THE TREATMENT OF TUMOURS
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The invention relates to proline derivatives and their salts, to pharmaceutical agents containing said derivatives and to the use of said agents for treating tumours. The invention also relates to methods for producing said compounds and pharmaceutical ag
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Page/Page column 39-40
(2008/06/13)
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- Processes for the preparation of carbapenem-type antibacterial agents
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A process for the preparation of a carbapenem antibacterial compound of the following formula (4) having a 1-alkylpyrrolidine structure or a salt thereof, a useful synthetic intermediate of the following formula (1) or a salt thereof, and a process for th
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- Peptide skeletal muscle relaxants
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Novel diquaternary polypeptides possessing skeletal muscle relaxation activity represented by the formulae: STR1 wherein: R is lower alkyl; R1 and R2 are lower alkyl or R1 and R2, together with the nitrogen to which they are attached form a heterocyclic ring having 5 to 7 member atoms; R3 is lower alkyl, [N,N-di(lower alkyl)-3-piperidinium](+), or [N,N-di(lower alkyl)-4-piperidinium](+) R4 is selected from the group consisting of t-butyl, benzyl or fluorenylmethyl; A1 is selected from the group consisting of trans-4-acetoxyproline, phenylalanine, glutamic acid-γ-methyl ester, or proline; AA2 is selected from the group consisting of phenylalanine, leucine, 3-(2-naphthyl)alanine, 3-(1-naphthyl)alanine, and 3-cyclohexylalanine; AA3 is proline when R3 is [N,N-di(lower alkyl)-3-piperidinium](+) or [N,N-di(lower alkyl)-4-piperidinium](+), and is Orn(δ-N(+) --R--R1 --R2) or Lys(ε-N(+) --R--R1 --R2) when R3 ia lower alkyl; AA4 is Orn(δ-N(+)--R--R1 --R2) or Lys(ε-N(+) --R--R1 --R2); Z(-) is a pharmaceutically acceptable anion; and (R)m R1 R2 N(+) represents the acceptable anion; (R)m R1 R2 N(+) -- represents the alpha amino group of AA1 ; and m represents an integer of 0 or 1 with the proviso that m is zero only when AA1 is trans-4-acetoxyproline or proline.
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- Synthese optisch aktiver neungliedriger Lactame durch zwitterionische Aza-Claisen-Reaktion
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Stichworte: Aza-Claisen-Reaktion * Azoninone * Chiralitaetstransfer * Lactame
- Diederich, Michel,Nubbemeyer, Udo
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p. 1095 - 1098
(2007/10/02)
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- Enantioselective Solvent Extraction of Neutral DL-Amino Acids in Two-Phase Systems Containing N-n-Alkyl-L-proline Derivatives and Copper(II) Ion
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Distribution behavior of neutral amino acid enantiomers was examined in the aqueous and organic solvent of a two-phase system containing cupric ion and N-n-dodecyl-L-proline or N-n-alkyl-L-hydroxyproline.Significant enentioselectivity was observed when n-butyl, n-amyl, or n-octyl alcohol was used as the organic solvent.Equilibrium constants of ligand exchange reaction for several amino acid enantiomers were estimated for the n-butyl alcohol-water system.The enantioselectivity seems to depend primarily on the difference of the stability of mixed ligand complexes in the organic phase.
- Takeuchi, Toshifumi,Horikawa, Rikizo,Tanimura, Takenori
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p. 1152 - 1155
(2007/10/02)
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