- L-GLUFOSINATE INTERMEDIATE AND L-GLUFOSINATE PREPARATION METHOD
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Provided are L-glufosinate intermediate preparation method or L-glufosinate preparation method, the method, for preparing L-glufosinate intermediate or L-glufosinate from an L-homoserine derivative, comprising a step of preparing a compound of Chemical Formula 2 from a compound of Chemical Formula 1.
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Paragraph 0160-0162
(2022/02/05)
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- A Unified Approach to Phytosiderophore Natural Products
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This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.
- Kratena, Nicolas,G?kler, Tobias,Maltrovsky, Lara,Oburger, Eva,Stanetty, Christian
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supporting information
p. 577 - 580
(2020/11/02)
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- Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence
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Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential anti-virulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of sub-inhibitory levels of ciprofloxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development.
- Hossain, Mohammad Anwar,Sattenapally, Narsimha,Parikh, Hardik I.,Li, Wei,Rumbaugh, Kendra P.,German, Nadezhda A.
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supporting information
(2019/11/26)
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- Synthesis of new chalcone-based homoserine lactones and their antiproliferative activity evaluation
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Three series of new homoserine lactone analogs were efficiently synthesized starting from methionine and further evaluated for their antiproliferative activity against different cancer cell lines. Among these compounds, some of the chalcone containing compounds 6a-n showed acceptable antiproliferative activity against prostate cancer cells DU145 and PC-3 with the IC50 values less than 10 μM. Compounds 6c, 6e and 6h inhibited growth of DU145 and PC-3 cells at low micromolar levels with the IC50 values ranging from 3.0 to 5.0 μM, much more potent than natural OdDHL. Compound 6e concentration-dependently inhibited colony formation and cell migration of DU145 cells. A synergistic effect on the growth inhibition and the apoptosis of DU145 cells was observed when compound 6e was used in combination with TRAIL. OdDHL or 6e treatment concentration-dependently activated TRAIL death receptor DR5 which may account for the observed synergistic effect of 6e or OdDHL with TRAIL on the growth inhibition and cell apoptosis. Compound 6e also inhibited migration of DU145 cells in a time- and concentration-dependent manner. The data suggest that quorum sensing molecules OdDHL and 6e may improve the sensitivity of DU145 cells toward TRAIL via activating DR5, compound 6e may be used as a potential lead compound for developing new TRAIL receptor agonists.
- Yu, Bin,Liu, Haoyue,Kong, Xiaoyan,Chen, Xinli,Wu, Chunli
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p. 500 - 511
(2019/01/03)
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- Synthesis and biological evaluation of novel L-homoserine lactone analogs as quorum sensing inhibitors of pseudomonas aeruginosa
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In this study, we synthesized four series of novel L-homoserine lactone analogs and evaluated their in vitro quorum sensing (QS) inhibitory activity against two biomonitor strains, Chromobacterium violaceum CV026 and Pseudomonas aeruginosa PAO1. Studies of the structure–activity relationships of the set of L-homoserine lactone analogs indicated that phenylurea-containing N-dithiocarbamated homoserine lactones are more potent than (Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone (C30), a positive control for biofilm formation. In particular, compared with C30, QS inhibitor 11f significantly reduced the production of virulence factors (pyocyanin, elastase and rhamnolipid), swarming motility, the formation of biofilm and the mRNA level of QS-related genes regulated by the QS system of PAO1. These results reveal 11f as a potential lead compound for developing novel antibacterial quorum sensing inhibitors.
- Liu, Haoyue,Gong, Qianhong,Luo, Chunying,Liang, Yongxi,Kong, Xiaoyan,Wu, Chunli,Feng, Pengxia,Wang, Qing,Zhang, Hui,Wireko
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p. 1088 - 1098
(2019/10/02)
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- A cogeneration process for producing sulfur and sulfur on behalf of acetate acid diester method (by machine translation)
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The invention technical field of chemical synthesis, in particular relates to a methionine as raw material production process for producing sulfur and sulfur on behalf of acetate acid diester method. The invention states the payment proportional to production for preparing sulfur and sulfur on behalf of acetate acid diester method, in order to methionine and halogenated acetic acid as the raw material, the preparation comprising a homoserine lactone hydrohalide salt (IV), a sulfur acetate (I) and sulfur on behalf of the b b acid diester (II) of the three kinds of chemical products, and each between the products easy to separate and purify. (by machine translation)
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Paragraph 0076; 0078
(2018/12/02)
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- Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives
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The ring-opening reaction of homoserine lactone with phenylmagnesium bromides was systematically examined. A reliable method to achieve β-amino acid precursors was developed by tuning the reaction conditions to favor mono-addition to the carbonyl moiety of the lactone.
- Gündo?du, ?zlem,Turhan, P?nar,K?se, Aytekin,Altunda?, Ramazan,Kara, Yunus
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p. 1163 - 1168
(2017/09/15)
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- Preparation method of high-optical-purity D- or L-selenomethionine
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The invention discloses a preparation method of high-optical-purity D- or L-selenomethionine. The preparation method comprises the following steps: by taking D- or L-methionine as initial raw materials and diethyl sulfate or halogenated alkyl acid or derived esters as alkylation reagents, generating sulfonium salt, desulfurizing and closing ring under acidic conditions, to produce alpha-amino-gama-butyrolactone halate, having addition reaction to alpha-amino-gama-butyrolactone halate with methyl selenol salt and opening ring, acidifying with organic acid, and recrystallizing to obtain D- or L-selenomethionine. The chemical purity of the product is more than or equal to 99%, and the high optical purity is more than or equal to 99%. The preparation method is low-cost and easily available in raw materials, simple in steps and easy to operate, simple in reaction conditions, and suitable for large-scale production.
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Paragraph 0028; 0029
(2017/08/30)
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- Method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of method
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The invention relates and belongs to the field of pesticide chemistry, and in particular relates to a method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of the method. The method takes L-methionine, concentrated hydrochloric acid and chloroacetic acid or bromoacetic acid as raw materials, and the L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride is obtained by a one-pot reaction. The method is simple in operation process and purification process, and high in yield; after the method is adopted, the production cost of L-glufosinate-ammonium is remarkably lowered.
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0040
(2017/04/29)
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- Synthesis of Chiral Bicyclic Guanidinium Salts using Di(imidazole-1-yl)methanimine
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A detailed account of the synthesis of chiral bicyclic guanidinium salts is presented. This work represents the first systematic investigation of an approach toward the challenging target molecules via a key guanylation step employing di(imidazole-1-yl)methanimine (6) followed by a two-fold cyclization, which resulted in guanidinium salts 8 and 10. Factors governing the regioselectivity of the final cyclization step are discussed based on further data obtained in the course of the attempted syntheses of two additional bicyclic guanidinium salts.
- Turo?kin, Aleksej,Honeker, Roman,Raven, William,Selig, Philipp
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p. 4516 - 4529
(2016/07/06)
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- Refined glufosinate preparation method
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The invention discloses a refined glufosinate preparation method. The refined glufosinate preparation method comprises the steps that 1, L-methionine and alpha-halogenated carboxylic acid or its derivative react under the effect of a phase transfer catalyst to obtain L-homoserine lactone hydrogen halide salt; 2, the L-homoserine lactone hydrogen halide salt and an amino protective reagent react to obtain a compound IV; 3, the compound IV performs ring-opening reaction with dihalogen sulfoxide, phosgene, triphosgene (BTC) or trimethyl halogenosilane to obtain a compound V, and the compound V is subjected to subsequent reaction treatment to obtain refined glufosinate, wherein the phase transfer catalyst is a quaternary ammonium salt phase transfer catalyst. The preparation method greatly improves the yield of the refined glufosinate, intermediate products revolved in reaction are easy to detect, the conditions are mild, and the refined glufosinate preparation method is suitable for industrial production.
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Paragraph 0050; 0051; 0052; 0068-0075; 0078-0081; 0102-0104
(2017/06/02)
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- A homoserine lactone compounds, its preparation process and its application
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The invention discloses homoserine lactone compounds as well as preparation methods and application thereof, relates to two series of compounds, i.e., N-acyl homoserine lactone and N-acetyl homoserine lactone, as well as preparation methods thereof, belonging to the chemical field of medicines, and in particular relates to a type of novel homoserine lactone compounds as shown in a chemical general formula described in the specification. According to the invention, mother nucleus of homoserine lactone is modified and an acyl side chain and a chalcone compound having large conjugated groups are introduced, thus improve quorum sensing inhibiting activity of the compound. The route preparation method is simple and easy to implement, and yield is high and reaches more than 70%.
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Paragraph 0052-0057
(2016/10/08)
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- Synthesis and biological evaluation of novel curcuminoid derivatives
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Curcuminoids have been reported to possess multiple bioactivities, such as antioxidant, anticancer and anti-inflammatory properties. Three novel series of curcuminoid derivatives (11a-h, 15a-h and 19a-d) with enhanced bioactivity have been synthesized. Among the synthesized compounds, 11b exhibited the most significant activity with an MIC of 0.5 μ M /mL against selected medically important Gram-positive cocci (S aureus and S viridans) and Gram-negative bacilli (E. coli and E. cloacae). The derivatives exhibited remarkable results in an antioxidant test with an IC50 2.4- to 9.3-folder smaller than curcuminoids. With respect to antiproliferative activity against Hep-G2, LX-2, SMMC7221 and MDA-MB-231, the derivatives exhibited an effect stronger than curcuminoids with an IC50 ranging from 0.18 to 4.25 μ M.
- Cao, Ya-Kun,Li, Hui-Jing,Song, Zhi-Fang,Li, Yang,Huai, Qi-Yong
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p. 16349 - 16372
(2015/01/08)
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- Method for Producing Bio-Based Homoserine Lactone and Bio-Based Organic Acid from O-Acyl Homoserine Produced by Microorganisms
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The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.
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Paragraph 0198-0200
(2014/10/16)
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- SYNTHETIC ANALOGS OF BACTERIAL QUORUM SENSORS
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Bacterial quorum-sensing molecule analogs having the following structures: and methods of reducing bacterial pathogenicity, comprising providing a biological system comprising pathogenic bacteria which produce natural quorum-sensing molecule; providing a synthetic bacterial quorum-sensing molecule having the above structures and introducing the synthetic quorum-sensing molecule into the biological system comprising pathogenic bacteria. Further is provided a method of targeted delivery of an antibiotic, comprising providing a synthetic quorum-sensing molecule; chemically linking the synthetic quorum-sensing molecule to an antibiotic to produce a quorum-sensing molecule-antibiotic conjugate; and introducing the conjugate into a biological system comprising pathogenic bacteria susceptible to the antibiotic.
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Page/Page column 3
(2011/04/14)
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- Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin
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The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(-)-α-N- phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better β-glucosidase inhibitor (IC50 32.4 μM toward β-glucosidase from almonds) and a better β-galactosidase inhibitor (IC50 5.9 mM for β-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for β-glucosidase and β-galactosidase, respectively).
- Venkataiah, Mallam,Reddipalli, Gowrisankar,Jasti, Lakshmi Swarnalatha,Fadnavis, Nitin W.
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experimental part
p. 1855 - 1860
(2012/01/13)
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- Enantioselective synthesis of (2S,3′R,7′Z)-N -(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone
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A concise enantioselective total synthesis of (2S,3′R,7′Z)-N- (3′-hydroxy-7′-tetradecenoyl)-homoserine lactone is described. Key feature of this protocol is a catalytic asymmetric hydrogenation and a prophenol-zinc-catalyzed diazo addition to imine reaction as genesis of chirality. Moreover, flexibility is built in the synthesis to generate enantioenriched analogs using catalytic amount of enantioenriched C 2-symmetric ligands.
- Kumaraswamy, Gullapalli,Jayaprakash, Neerasa
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supporting information; experimental part
p. 6500 - 6502
(2011/02/22)
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- Preparation of vinylglycines by thermolysis of homocysteine sulfoxides
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The synthesis and efficacy of preparing Cbz-VG-OMe (1) by thermolysis of alkyl and aryl homocysteine sulfoxides were surveyed. This investigation determined that aryl sulfoxide analogs were more effective for the reaction and that the 2-nitrophenyl analog 10f possessed a unique ability to syn eliminate at temperatures as low as 100 °C. The thermolysis of sulfoxide 10f was additionally discovered to occur under toluene reflux and when sodium acetate was added, Cbz-VG-OMe (1) could be obtained in high purity by simple filtration of the precipitated sulfenic acid byproduct 12. This mild protocol which was also applied in the synthesis of VG dipeptide 13 would have utility in the general synthesis of olefins and alkenes from 2-nitrophenylsulfoxides.
- Patel, Sravan Kumar,Long, Timothy E.
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supporting information; experimental part
p. 5067 - 5070
(2009/12/01)
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- An unusual conformation of α-haloamides due to cooperative binding with zincated porphyrins
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CD and NMR spectroscopic evidence of cooperative binding between an α-halogen atom and a carboxamide group with a zinc porphyrin leads to an unprecedented conformation for the determination of the absolute stereochemistry of α-haloamides (α-halocarboxylic acids derivatized with 1,4-phenylenediamine) through the use of exciton-coupled circular dichroism (ECCD). With the use of chiral lactams, whose rotomeric contributions are minimized, both ECCD and NMR spectroscopy demonstrate that the porphyrin favors binding to the side of the sterically more demanding halogen atom as compared to the smaller hydrogen atom. In all, the data is strongly suggestive of an unusual conformation not observed before for α-chiral amides. A mnemonic for determining the absolute stereochemistry of α-halogenated carboxylic acids is provided.
- Tanasova, Marina,Yang, Qifei,Olmsted, Courtney C.,Vasileiou, Chrysoula,Li, Xiaoyong,Anyika, Mercy,Borhan, Babak
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supporting information; experimental part
p. 4242 - 4253
(2011/02/25)
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- Method for production of methionine from homoserine
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The invention relates to a method for production of D- and/or L-methionine via D- and/or L-homoserine with subsequent chemical transformation to give methionine.
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Page/Page column 16-17
(2008/06/13)
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- Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway
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(Chemical Equation Presented) Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.
- Xiao, Youli,Lee, Kent,Liu, Pinghua
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supporting information; experimental part
p. 5521 - 5524
(2009/06/28)
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- Optical resolution by preferential crystallization of (RS)-α-amino-γ-butyrolactone hydrochloride
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(RS)-α-Amino-γ-butyrolactone hydrochloride [(RS)-ABL·HCl] was found to exist as a conglomerate based on the infrared spectrum, solubility, and melting point. Optical resolution by preferential crystallization of (RS)-ABL·HCl was achieved to yield (R)- and (S)-ABL·HCl. The obtained (R)- and (S)-ABL·HCl were recrystallized, taking into account the solubility of (RS)-ABL·HCl to give optically pure (R)- and (S)-ABL·HCl.
- Shiraiwa, Tadashi,Miyazaki, Hideya,Ohta, Atsushi,Waki, Yukitaka,Yasuda, Masahiro,Morishita, Toshimitsu,Kurokawa, Hidemoto
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p. 2322 - 2325
(2007/10/03)
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- Synthesis of (S)-2-amino-1,1-diphenylbutan-4-ol; conversion of an α-amino acid into an α-(diphenylmethyl) amine without loss of optical purity
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The title amino-alcohol 4 is an intermediate for the preparation of chiral bicyclic amidines and guanidines, and also for polyamines with potential as ligands in enantioselective catalysis. It has been synthesized from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved non-trivial, but was eventually achieved through the application of catalytic transfer methodology to the bis-acetyl derivative 14.
- Boyle,Davis,Dempsey,Hosken
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p. 2819 - 2828
(2007/10/03)
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- Synthesis of L-(+)-selenomethionine
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A novel three-pot synthesis of L-(+)-selenomethionine suitable for small and large scale preparations is presented. The method gives high optical purity and avoids evil smelling selenium species.
- Koch,Buchardt
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p. 1065 - 1067
(2007/10/02)
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- Asymmetric Synthesis of α-Amino Acids via Cationic Aza-Cope Rearrengements
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Ene-iminium intermediates resulting from reaction between glyoxal and β-amino alcohols rearrange by an aza-Cope process.Three different tandem reactions are thus carried out; their first component is this cationic rearrangement, the second step being either an iminium hydrolysis, a nucleophile-induced ene-iminium cyclization or a Mannich reaction.The last two sequences lead to homochiral proline derivatives.
- Agami, Claude,Couty, Francois,Lin, Jing,Mikaeloff, Axelle,Poursoulis, Michel
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p. 7239 - 7250
(2007/10/02)
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- Reinvestigation of the Base-Induced Ring Closure of Methylsulfonium Salts of N-Trityl-(S)-methioninehydroxamide and Derivatives
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Base-induced ring closure of methylsulfonium salts of hydroxamate derivatives of N-trityl-(S)-methionine provides five-membered heterocycles resulting from nucleophilic displacement of Me2S by either the O- or N-atom of the amide function.A three-step sequence starting from N-trityl-(S)-methionine 1-hydroxybenzotriazolyl ester has previously been used to provide a 3percent yield of a compound described as (S)-4-(N-tritylamino)-1,2-oxazinan-3-one.Using a new five-step sequence the same product was isolated in 34percent overall yield and is now shown to be (S)-2-hydroxy-imino-3-(N-tritylamino)oxolane.
- Papaioannou, Dionissios,Barlos, Kleomenis,Francis, George W.,Brekke, Trond,Aksnes, Dagfinn W.,Maartmann-Moe, Knut
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p. 189 - 194
(2007/10/02)
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- A CONVENIENT NEW SYNTHESIS OF HOMOSERINE LACTONE
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N-trityl L-homoserine lactone is synthesised in three steps from L-aspartic acid.
- Baldwin, J. E.,North, M.,Flinn, A.
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p. 3167 - 3168
(2007/10/02)
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- Asymmetric Syntheses via Heterocyclic Intermediates; XXVII. Enantioselective Synthesis of (R)-Homoserine Methyl Esters and (R)-α-Methyl-homoserine Methyl Esters and of the Corresponding α-Amino-γ-lactones by the Bis-lactim Ether Method
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An asymmetric synthesis of various (R)-homoserine methyl esters and (R)-α-methylhomoserine methyl esters starting from the bis-lactim ethers of cyclo-(L-Val-Gly) and cyclo-(L-Val-Ala) and oxiranes is described
- Gull, Reinhold,Schoellkopf, Ulrich
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p. 1052 - 1055
(2007/10/02)
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- Preparation of (S)-3-Azidodihydrofuran-2(3H)-one (α-Azidobutyrolactone) (1), a Usefull Chiral Synthon
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(S)-3-Azidodihydrofuran-2(3H)-one (α-Azidobutyrolactone) (1) has been resolved through the brucine salt of the corresponding hydroxy acid (2).Both (1), and various derivatives of (2), are useful synthons for the preparation of L-amino acids related to L-homoserine.
- Davis, Michael,Dudman, Nicholas, P. B.,White, Hume F.
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p. 621 - 624
(2007/10/02)
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