13283-91-5Relevant academic research and scientific papers
Natural product inhibitors of fatty acid biosynthesis: synthesis of the marine microbial metabolites pseudopyronines A and B and evaluation of their anti-infective activities
Giddens, Anna C.,Nielsen, Lone,Boshoff, Helena I.,Tasdemir, Deniz,Perozzo, Remo,Kaiser, Marcel,Wang, Feng,Sacchettini, James C.,Copp, Brent R.
, p. 1242 - 1249 (2008)
Total syntheses of the title natural products, pseudopyronines A (1) and B (2), have been achieved using methyl β-oxo carboxylic ester starting materials. The natural products and a small set of structurally related compounds were evaluated for growth inh
Short syntheses of (±)-tetraponerines-5 and -6. The structures of tetraponerines-1 and -2, and a revision of the structures of (+)-tetraponerines-5 and 6.
Devijver,Macours,Braekman,Daloze,Pasteels
, p. 10913 - 10922 (1995)
The structures and absolute configurations of (+)-tetraponerines-5 and -6 [(+)-T-5 and (+)-T-6], from the poison gland of the ant Tetraponera sp., were reassigned as 7 and 8, respectively, on the basis of extensive two-dimensional NMR and CD studies. These results led to structure proposals 9 for T-1 and 10 for T-2, the two minor alkaloids of the venom. The structures and relative configuration of T-5 and T-6 were subsequently confirmed by short stereoselective syntheses.
Synthesis of (-)-Syringolides 1 and 2
Kuwahara, Shigefumi,Moriguchi, Masahiko,Miyagawa, Kazuhiro,Konno, Masako,Kodama, Osamu
, p. 8809 - 8814 (1995)
The enatioselective synthesis of (-)-syringolides 1 and 2 which were isolated as specific elicitors produced by Pseudomonas syringae pv. tomato was accomplished in 11 steps from diethyl D-tartrate.The specific rotations of synthetic samples were in good accord with those of the natural syringolides, and synthetic syringolide 2 showed almost the same biological activity as that of natural syringolide 2.
Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds
Radivojevic, Jelena,Skaro, Sanja,Senerovic, Lidija,Vasiljevic, Branka,Guzik, Maciej,Kenny, Shane T.,Maslak, Veselin,Nikodinovic-Runic, Jasmina,OConnor, Kevin E.
, p. 161 - 172 (2016/01/09)
A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.87.0 mM and 0.16.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.
A stereoselective and practical synthesis of (E)-α,β-unsaturated ketones from aldehydes
Balducci, Evita,Attolino, Emanuele,Taddei, Maurizio
experimental part, p. 311 - 318 (2011/02/28)
α,β-Unsaturated ketones can be prepared by reaction of differently substituted β-keto acids and aldehydes. The reaction is carried out under organocatalysis (β-alanine, 0.5 equiv.) and generates the enones with high E selectivity (>95%). This version of the Verley-Doebner modification of the Knoevenagel reaction is a practical alternative to the classic Horner-Wadsworth-Emmons (HWE) reaction without the formation of high molecular weight byproducts. The process makes use of simple reagents and can be applied to large-scale synthesis under conditions compatible with atom-economy principles. Differently substituted aliphatic, aromatic, or heteroaromatic α,β-unsaturated ketones can be prepared. An example of a hydroformylation/Verley-Doebner Knoevenagel telescoped process is also described. The conditions used in the Knoevenagel reaction to prepare conjugated esters under amino acid organocatalysis can be applied also for the synthesis of α,β unsaturatedketones. β-Keto acids are prepared byhydrogenolysis of the corresponding benzyl ester and react easily with aldehydes to give the α,β-unsaturated ketones without formation of high molecular weight byproducts. Copyright
COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA
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Page/Page column 17, (2008/06/13)
The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.
Small molecule inhibitors of bacterial quorum sensing and biofilm formation
Geske, Grant D.,Wezeman, Rachel J.,Siegel, Adam P.,Blackwell, Helen E.
, p. 12762 - 12763 (2007/10/03)
Bacteria monitor their local population densities using small molecules (or autoinducers) in a process known as quorum sensing. Here, we report a new and efficient synthetic route to naturally occurring bacterial autoinducers [N-acyl L-homoserine lactones (AHLs)] that is readily amenable to the synthesis of analogues. This route has been applied in the first synthesis of a library of non-native AHLs. Evaluation of these compounds in bacterial reporter gene and biofilm assays has revealed a potent set of quorum sensing antagonists. These ligands will serve as valuable new tools to explore the role of quorum sensing in bacterial pathogenesis. Copyright
Enantioselective reduction of β-keto acids with engineered streptomyces coelicolor
Booker-Milburn, Kevin I.,Gillan, Rebecca,Kimberley, Meriel,Taguchi, Takaaki,Ichinose, Koji,Richard Stephenson,Ebizuka, Yutaka,Hopwood, David A.
, p. 1121 - 1125 (2007/10/03)
Compelling evidence for the intermediacy of the free β-keto acid 1, rather than the corresponding enzyme-bound thiolate as previously proposed, in the biosynthesis of the antibiotic actinorhodin (2) was obtained from studies of the enantioselective reduction of a range of β-keto acids by the engineered strain of S. coelicolor CH999/pIJ5675. This excellent whole-cell biotransformation system gave the desired S β-hydroxy acids with >95% ee.
Formal synthesis of (-)-syringolide 1 starting from D-xylose based on a biomimetic strategy
Yoda, Hidemi,Kawauchi, Miho,Takabe, Kunihiko,Hosoya, Ken
, p. 1895 - 1898 (2007/10/03)
An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.
A novel convenient route to the naturally occurring 3-oxoacyl-L-homoserinelactones and related bacterial autoinducers
Dekhane, Mouloud,Douglas, Kenneth T.,Gilbert, Peter
, p. 1883 - 1884 (2007/10/03)
The naturally occurring 3-oxohexanoyl-L-homoserinelactone (1a), a bacterial autoinducer has been prepared in 47% overall yield by condensing stable 3-oxohexanoic acid (2), prepared by hydrolysis from the corresponding ester (3), with L-homoserinelactone using hydroxybenzotriazole (HOBT) and dicyclohexylcarbodiimide (DCC) in non-aqueous media.
