Selective Synthesis of Unsaturated N-Acylethanolamines by Lipase- Catalyzed N-Acylation of Ethanolamine with Unsaturated Fatty Acids

Plastina, Pierluigi; Meijerink, Jocelijn; Vincken, Jean‐Paul; Gruppen, Harry; Witkamp, Renger F.; Gabriele, Bartolo

doi:10.2174/157017809789124885

Cited by 36 publications

(53 citation statements)

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“…35 When hydrazine was used as substrate in the reaction with an excess of octanoic acid, N,N'-dioctoylhydrazine was obtained in good yields. 49 40 …”

Section: Hydroxamic Acids and Acyl Hydrazinesmentioning

confidence: 99%

“…38 It was also found that the monoacylated ester was a rapidly formed intermediate in dioxane, which subsequently was transformed into the thermodynamically more stable amide. However, no such ester intermediate was observed when the reaction was performed 40 in n-hexane.…”

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confidence: 95%

“…Although the amide bond can be formed from the corresponding ammonium carboxylate salt upon heating, this reaction has generally been considered to be of limited preparative value. 5 40 Furthermore, the high activation barrier for the direct coupling of a carboxylic acid and an amine can only be overcome using forcing reaction conditions. 6 In order to circumvent these problems, the amide bond is usually formed via an activated carboxylic acid.…”

Section: Introductionmentioning

confidence: 99%

“…In 2002, the first protocol employing a protease as biocatalyst for the direct amidation of carboxylic acids was published by Ulijn et al 31 It was also the first paper to describe the catalytic 40 formation of peptides from two amino acids under synthetically useful reaction conditions. The amine component of the reaction, L-phenylalanine, was attached to a PEGA 1900 -support via a Wang linker and then reacted with a variety of protected amino acids in aqueous media with thermolysin as catalyst.…”

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confidence: 99%

“…39 By running the reaction at 90 ºC and adding the ethanolamine in portions to keep it protonated at all times, water could be distilled off under vacuum to afford the surfactant amide in 95% yield. Surfactant ethanolamides were also synthesised by Plastina et al 40 Novozym® 435 was used as catalyst to afford six 50 different ethanolamides from fatty acids in yields ranging from 80-88%. The reaction was performed in hexane at 40 ºC, with a catalyst loading of 250 mg/mmol substrate and a 1:1 molar ratio of amine to acid.…”

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confidence: 99%

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Catalytic amide formation from non-activated carboxylic acids and amines

et al. 2014

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The amide functionality is found in a wide variety of biological and synthetic structures such as proteins, polymers, pesticides and pharmaceuticals. Due to the fact that synthetic amides are still mainly produced by the aid of coupling reagents with poor atom-economy, the direct catalytic formation of amides from carboxylic acids and amines has become a field of emerging importance. A general, efficient and selective catalytic method for this transformation would meet well with the increasing criterias for green 10 chemistry. This review covers catalytic and synthetically relevant methods for direct condensation of carboxylic acids and amines. A comprehensive overview of homogeneous and heterogeneous catalytic methods is presented, covering biocatalysis, Lewis acid catalysts based on boron and metals as well an assortment of other types of catalysts.

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“…35 When hydrazine was used as substrate in the reaction with an excess of octanoic acid, N,N'-dioctoylhydrazine was obtained in good yields. 49 40 …”

Section: Hydroxamic Acids and Acyl Hydrazinesmentioning

confidence: 99%

mentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Catalytic amide formation from non-activated carboxylic acids and amines

et al. 2014

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Different amplifying mechanisms of interleukin‐17 and interferon‐γ in Fcγ receptor–mediated cartilage destruction in murine immune complex–mediated arthritis

Grevers¹,

Lent²,

Koenders³

et al. 2009

Arthritis & Rheumatism

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Objective. Previously, we reported that interferon-␥ (IFN␥) aggravates cartilage destruction in immune complex (IC)-mediated arthritis via up-regulation of activating Fc␥ receptors (Fc␥R). Recently, we found that interleukin-17 (IL-17) also aggravates cartilage destruction in arthritis models in which ICs are involved, but the underlying mechanism remains unknown. This study was undertaken to determine the role of IL-17 in Fc␥R-mediated cartilage destruction in IC-mediated arthritis and to compare its effect with that of IFN␥.Methods. IC-mediated arthritis was passively induced in ␥-chain ؊/؊ mice, which lack functional activating Fc␥R, and in wild-type controls. AdIL-17 or a control vector was injected into the knee joints 1 day prior to induction of IC-mediated arthritis. Knee joints were isolated for histologic analysis, and synovium samples were obtained for

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