- Oxygenated N-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium Roseovarius tolerans EL-164
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The marine bacterium Roseovarius tolerans EL-164 (Rhodobacteraceae) can produce unique N-acylalanine methyl esters (NAMEs) besides strucutrally related N-acylhomoserine lactones (AHLs), bacterial signaling compounds widespread in the Rhodobacteraceae. The structures of two unprecedented NAMEs carrying a rare terminally oxidized acyl chain are reported here. The compounds (Z)-N-16-hydroxyhexadec-9-enoyl-l-alanine methyl ester (Z9-16-OH-C16:1-NAME, 3) and (Z)-N-15-carboxypentadec-9-enoyl-l-alanine methyl ester (16COOH-C16:1-NAME, 4) were isolated, and the structures were determined by NMR and MS experiments. Both compounds were synthesized to prove assignments and to test their biological activity. Finally, non-natural, structurally related Z9-3-OH-C16:1-NAME (18) was synthesized to investigate the mass spectroscopy of structurally related NAMEs. Compound 3 showed moderate antibacterial activity against microorganisms such as Bacillus, Streptococcus, Micrococcus, or Mucor strains. In contrast to AHLs, quorum-sensing or quorum-quenching activity was not observed.
- Bruns, Hilke,Herrmann, Jennifer,Müller, Rolf,Wang, Hui,Wagner D?bler, Irene,Schulz, Stefan
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p. 131 - 139
(2018/02/07)
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- Chemoenzymatic preparation of musky macrolactones
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Abstract A chemoenzymatic approach to some musk macrolactones has been explored by the optimization of macrolactonization catalyzed by Candida antarctica lipase B (Novozym 435). This fast and high yield optimized methodology represents a large improvement to previously reported results. The methodology was applied to the preparation of 16-hexadecanolide, exaltolide, ambrettolide and (15R)-15-hexadecanolide.
- Fortunati, Tancredi,D'Acunto, Mariantonietta,Caruso, Tonino,Spinella, Aldo
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p. 2357 - 2362
(2015/03/30)
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- Total synthesis of isoprostanes derived from adrenic acid and EPA
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Enantiomerically enriched F2-dihomo-isoprostanes and F 3-isoprostanes have been synthesized. Such compounds are derived from the action of reactive oxygen species on the phospholipid-bound polyunsaturated fatty acids (PUFA), adrenic
- Oger, Camille,Bultel-Ponce, Valerie,Guy, Alexandre,Durand, Thierry,Galano, Jean-Marie
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experimental part
p. 2621 - 2634
(2012/06/30)
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- SCRIPTAID ISOSTERES AND THEIR USE IN THERAPY
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Compounds of the invention are of the formula (I); wherein: … is a double bond and X is C; or … is a single bond and X is N, CH or CQR1; and wherein: n is 1 to 10; R is H or QR1; each R' is independently selected from H and QR1
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Page/Page column 30
(2010/08/09)
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- Development of new methods toward efficient immobilization of chiral catalysts
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BINOL moieties are efficiently immobilized onto the surface of a micelle-derived spherical polymer and a monolayer-protected Au cluster (Au-MPC). Ti-BINOLate complexes generated from the BINOL immobilized polymer and Au-MPC are found to promote catalytic
- Takizawa, Shinobu,Patil, Mahesh L.,Marubayashi, Kazuyoshi,Sasai, Hiroaki
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p. 6512 - 6528
(2008/02/05)
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- Structurally simple trichostatin A-like straight chain hydroxamates as potent histone deacetylase inhibitors
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A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15
- Woo, Soon Hyung,Frechette, Sylvie,Khalil, Elie Abou,Bouchain, Giliane,Vaisburg, Arkadii,Bernstein, Naomy,Moradei, Oscar,Leit, Silvana,Allan, Martin,Fournel, Marielle,Trachy-Bourget, Marie-Claude,Li, Zuomei,Besterman, Jeffrey M.,Delorme, Daniel
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p. 2877 - 2885
(2007/10/03)
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- Titanium(III) mediated regiospecific reduction of vinyl epoxides
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A highly regiospecific reduction of vinyl epoxides to allyl alcohols with Cp2TiCl is described.
- Yadav,Shekharam,Srinivas
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p. 7973 - 7976
(2007/10/02)
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