Ruthenium catalysed oxidation without CCl4 of oleic acid, other monoenic fatty acids and alkenes

Zimmermann, F.; Meux, Eric; Mieloszynski, J. L.; Lecuire, J.M.; Oget, Nicolas

doi:10.1016/j.tetlet.2005.03.052

Cited by 85 publications

(62 citation statements)

References 20 publications

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“…This is presumably due to the closer proximity of the carbonyl group to the electron withdrawing perfluoroalkyl chain (cf. n(C5 5O) = 1712 cm À1 for CH 3 (CH 2 ) 7 CO 2 H [11]). …”

Section: Resultsmentioning

confidence: 99%

Thermomorphic metal scavengers: A synthetic and multinuclear NMR study of highly fluorinated ketones and their application in heavy metal removal

Baker

McCabe

O’Brien

et al. 2010

Journal of Fluorine Chemistry

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“…This is presumably due to the closer proximity of the carbonyl group to the electron withdrawing perfluoroalkyl chain (cf. n(C5 5O) = 1712 cm À1 for CH 3 (CH 2 ) 7 CO 2 H [11]). …”

Section: Resultsmentioning

confidence: 99%

Thermomorphic metal scavengers: A synthetic and multinuclear NMR study of highly fluorinated ketones and their application in heavy metal removal

Baker

McCabe

O’Brien

et al. 2010

Journal of Fluorine Chemistry

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“…Oxidative cleavage of alkene 4 into 5 was performed by the Sharpless method with ruthenium chloride as catalyst and sodium periodate as oxidant 44, 45 in solvent system H 2 O/AcOEt/MeCN (3/2/2). 46 N,N’ -carbonyldiimidazole (CDI) mediated coupling of carboxylic acid 5 with N-O -dimethylamine quantitatively led to Weinreb amide 6 . N -methoxy- N -methylamides are well-known reagents for the synthesis of ketones from carboxylic acids in the presence of Grignard or organolithium reagents.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of N8-acetylspermidine analogues as inhibitors of bacterial acetylpolyamine amidohydrolase

Decroos

Bowman

Christianson

2013

Bioorganic & Medicinal Chemistry

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Polyamines are small essential polycations involved in many biological processes. Enzymes of polyamine metabolism have been extensively studied and are attractive drug targets. Nevertheless, the reversible acetylation of polyamines remains poorly understood. Although eukaryotic N8-acetylspermidine deacetylase activity has already been detected and studied, the specific enzyme responsible for this activity has not yet been identified. However, a zinc deacetylase from Mycoplana ramosa, acetylpolyamine amidohydrolase (APAH), has been reported to use various acetylpolyamines as substrates. The recently solved crystal structure of this polyamine deacetylase revealed the formation of an “L”-shaped active site tunnel at the dimer interface, with ideal dimensions and electrostatic properties for accommodating narrow, flexible, cationic polyamine substrates. Here, we report the design, synthesis, and evaluation of N8-acetylspermidine analogues bearing different zinc binding groups as potential inhibitors of APAH. Most of the synthesized compounds exhibit modest potency, with IC50 values in the mid-micromolar range, but compounds bearing hydroxamate or trifluoromethylketone zinc binding groups exhibit enhanced inhibitory potency in the mid-nanomolar range. These inhibitors will enable future explorations of acetylpolyamine function in both prokaryotes and eukaryotes.

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“…Precursors for ruthenium catalysts such as RuCl 3 , RuO 2 , and Ru(acac) 3 were applied in the presence of chlorine under strongly basic conditions [52][53][54] or with preformed NaOCl [9,55], peracetic acid [9,56], or NaIO 4 [9,57] as oxidants. In these reactions, RuO 4 is supposed to be the in situ formed catalytically active species.…”

Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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Ruthenium catalysed oxidation without CCl4 of oleic acid, other monoenic fatty acids and alkenes

Cited by 85 publications

References 20 publications

Thermomorphic metal scavengers: A synthetic and multinuclear NMR study of highly fluorinated ketones and their application in heavy metal removal

Thermomorphic metal scavengers: A synthetic and multinuclear NMR study of highly fluorinated ketones and their application in heavy metal removal

Synthesis and evaluation of N8-acetylspermidine analogues as inhibitors of bacterial acetylpolyamine amidohydrolase

Synthesis of azelaic acid from vegetable oil‐based feedstocks

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