Studies Directed toward the Synthesis of Plasmalogens. II. (±)-cis- and -trans-3-(n-Hexadec-1'-enyloxy)-1,2-propanediol<sup>1</sup>

Jc, Craig; Dp, Hamon

doi:10.1021/jo01023a044

Cited by 33 publications

(6 citation statements)

References 6 publications

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“…Then, we used the method of Bhatia et al to introduce the alkylether moiety ( Figure 2 ). First, the alkyl alcoholate was prepared by deprotonation of the alcohol with NaH and then this alcoholate reacted with the tosylated solketal 2 [ 42 ]. After work-up, the expected compounds 3a – i were isolated in 60–96% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

et al. 2018

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Natural O-alkyl-glycerolipids, also known as alkyl-ether-lipids (AEL), feature a long fatty alkyl chain linked to the glycerol unit by an ether bond. AEL are ubiquitously found in different tissues but, are abundant in shark liver oil, breast milk, red blood cells, blood plasma, and bone marrow. Only a few AEL are commercially available, while many others with saturated or mono-unsaturated alkyl chains of variable length are not available. These compounds are, however, necessary as standards for analytical methods. Here, we investigated different reported procedures and we adapted some of them to prepare a series of 1-O-alkyl-glycerols featuring mainly saturated alkyl chains of various lengths (14:0, 16:0, 17:0, 19:0, 20:0, 22:0) and two monounsaturated chains (16:1, 18:1). All of these standards were fully characterized by NMR and GC-MS. Finally, we used these standards to identify the AEL subtypes in shark and chimera liver oils. The distribution of the identified AEL were: 14:0 (20–24%), 16:0 (42–54%) and 18:1 (6–16%) and, to a lesser extent, (0.2–2%) for each of the following: 16:1, 17:0, 18:0, and 20:0. These standards open the possibilities to identify AEL subtypes in tumours and compare their composition to those of non-tumour tissues.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

et al. 2018

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“…The aldehydes are readily regenerated by treatment with either aqueous acid [35] or base. [36] Regeneration of the aldehyde by treatment of the bisulfite adduct with aqueous formaldehyde was straightforward, allowing for the isolation of various aldehydes from the organic layer (Table 1). [37] Table 1.…”

Section: Resultsmentioning

confidence: 99%

Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents

Bailey

Clary

Tansakul

et al. 2015

Tetrahedron Letters

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“…The spectrum of III showed the signals at δ 5.88 ppm and at 4.39 ppm which are characteristic of the c/s-enol ether grouping whereas the trans isomer would have shown a doublet near 6.20 ppm, and a pair of triplets near 4.78 ppm for the hydrogen at C-2' 14 . The spectrum of I was similar to that of the cis-alk-lenyl glycerol ethers obtained from the alk-1-eny 1 diglycerides of ratfish liver 6 .…”

Section: -Cis-alk-γ-enyl Ethers Of Glycerolmentioning

confidence: 99%

“…It was shown that these diol lipids occur as enol ether esters ("aldehydogenic diol lipids") in rat liver, corn seeds and soil yeast (Lipomyces spec.) Syntheses which eliminate formation of the 2-isomer were suggested 14 " 16 , but the preferential formation of trans enol ethers could not be prevented. Alk-1-enyl diol phosphatides have not been detected so far.…”

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confidence: 99%

Alk-1-enyl Ethers of Glycerol and Ethanediol

Baumann¹,

Schmid²,

Kramer³

et al. 1968

Hoppe-Seyler´s Zeitschrift für physiologische Chemie

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Procedures are described for the preparation of neutral aldehydogenic lipids derived from glycerol and ethanediol: Hydrogenolysis of the total lipids of bovine heart muscle with lithium aluminum hydride yields a mixture of lipids from which optically active l-c/'s-alk-l'-enyl glycerol ethers are isolated as a pure lipid class. Periodate oxidation of the alk-1-enyl glycerol ethers and reduction of the intermediate alk-1-enyl glycol-Zusammenfassung: Alkeny lather des Glycerins und Äthandiols. Methoden zur Darstellung neutraler aldehydogener Lipide werden beschrieben: Hydrogenolyse der Gesamtlipide des Rinderherzmuskels mit Lithiumalanat ergibt ein Gemisch von Lipiden, aus dem optisch aktive l-[\-cis-Mkenyl]-glycerinäther als reine Lipidklasse isoliert werden. Perjodatspaltung der Alkenylglycerinäther und Reduktion der intermediär gebildeten Long-chain alk-1-enyl ethers of glycerol occur as constituents of ionic 1 and neutral 2 lipids. Alk-1-enyl acyl glycerophosphatides ("plasmalogens") have not been obtained as pure lipid classes, whereas

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Studies Directed toward the Synthesis of Plasmalogens. II. (±)-cis- and -trans-3-(n-Hexadec-1'-enyloxy)-1,2-propanediol¹

Cited by 33 publications

References 6 publications

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents

Alk-1-enyl Ethers of Glycerol and Ethanediol

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Studies Directed toward the Synthesis of Plasmalogens. II. (±)-cis- and -trans-3-(n-Hexadec-1'-enyloxy)-1,2-propanediol1

Cited by 33 publications

References 6 publications

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents

Alk-1-enyl Ethers of Glycerol and Ethanediol

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Product

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Studies Directed toward the Synthesis of Plasmalogens. II. (±)-cis- and -trans-3-(n-Hexadec-1'-enyloxy)-1,2-propanediol¹