ChemInform Abstract: FATTY ACIDS LABELED IN THE Ω POSITION WITH A Γ‐EMITTING RADIOACTIVE NUCLIDE

Riche, F.; Mathieu, J. P.; Vincencs, M.; Bardy, A.; Comet, M.; Vidal, Miquel

doi:10.1002/chin.198425129

Cited by 2 publications

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“…The synthesis of the ω‐hydroxystearic acid 10a (Scheme ) started with the “acetylene zipper” reaction43 of oct‐3‐yn‐1‐ol ( 8 ) in which the triple bond was moved to the end of the carbon–carbon chain. The resulting oct‐7‐yn‐1‐ol ( 7 ) was coupled with 10‐bromodecanoic acid ( 6 ) in liquid ammonia in the presence of lithium amide to give 18‐hydroxyoctadec‐11‐ynoic acid ( 9 ) in 50 % yield 41c. It turned out to be necessary to use freshly distilled ammonia; otherwise the impurities dramatically inhibited the coupling reaction.…”

Section: Resultsmentioning

confidence: 99%

“…It turned out to be necessary to use freshly distilled ammonia; otherwise the impurities dramatically inhibited the coupling reaction. The triple bond in 9 was hydrogenated over PtO 2 to yield ω‐hydroxyoctadecanoic acid ( 10a ) 41c. Direct conversion of the ω‐hydroxy group to afford the corresponding ω‐bromo acid 10b 44 furnished the common precursor for both the ω‐amino‐ and the ω‐mercaptostearic acids.…”

Section: Resultsmentioning

confidence: 99%

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New GM1 Ganglioside Derivatives for Selective Single and Double Labelling of the Natural Glycosphingolipid Skeleton

et al. 2009

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Selective single and double labelling of the natural ganglioside GM1 enables one to introduce various markers into different parts of the glycosphingolipid molecule without changing the natural skeleton. To that end, N‐Fmoc‐2‐amino‐, N‐Fmoc‐18‐amino‐ and S‐(ethoxythiocarbonyl)‐18‐mercaptostearic acids have been prepared and coupled with the primary amino group in the sphingosine part of lyso‐GM1 and deAc‐deAcyl‐GM1 gangliosides. The products of these coupling reactions – building blocks 16a, 16b, 16c, 26 and 27 – may be used for the synthesis of GM1 derivatives with one or two fluorescent dye moieties or other labels of various polarities. Examples of various labelling strategies, using hydrophilic and lipophilic photostable fluorescent dyes, have been made available. The GM1 derivatives 17a, 22a and 23c labelled with the fluorescent dye ATTO 647N or the doubly labelled derivative 25b can be used as probes in fluorescence correlation spectroscopy (in conventional microscopy or stimulated emission depletion nanoscopy) to study the diffusion of lipid analogues in model or live cell membranes.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

New GM1 Ganglioside Derivatives for Selective Single and Double Labelling of the Natural Glycosphingolipid Skeleton

et al. 2009

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“…The resulting 7-octyn-1-ol (271) was coupled with 10bromodecanoic acid (272) in liquid ammonia in the presence of lithium amide to give 18hydroxyoctadec-11-ynoic acid (273) in 50% yield. [116] It turned out to be necessary to use freshly distilled ammonia, otherwise the impurities dramatically inhibited the coupling reaction. The triple bond in 273 was hydrogenated over PtO 2 to yield ω-hydroxyoctadecanoic acid (274).…”

Section: Synthesis Of Ganglioside Derivatives With α-Or ω-Amino-and ω...mentioning

confidence: 99%

Fluorescent and Photochromic Fluorescent Compounds for Applications in Optical Nanoscopy

Polyakova¹

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Scheme 3.9. Modifications of symmetric 1,2-bis(3-thienyl)ethenes. Photochromic fluorescent 1,2-bis(3-thienyl)perfluorocyclopentenesFluorescent photochromic compounds described in the literature may be used as optical memory materials and fluorescent probes. Non-destructive readout capability is indespensible for applications in the field of recording media. The fluorescence readout method is very sensitive, and the light with low power energy destroys the recorded information to a minimal extent.Three separated wavelength for writing, reading, and erasing cycles allow to change the fluorescence intensity reversibely.Several photochromic fluorescent diarylethenes were reported in the last 14 years. [35] Fluorescence modulation achieved by changes in conjugationThe fluorescence may be quenched by the photoinduced electron transfer (PET), and several fluorescent photoswitchers based on this principle have been synthesized. The compounds 39 and 40 designed by Tsvigoulis and Lehn at the begining of the 1990s have good fluorescence modulation. [36]

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ChemInform Abstract: FATTY ACIDS LABELED IN THE Ω POSITION WITH A Γ‐EMITTING RADIOACTIVE NUCLIDE

Abstract: Aus den Dibromalkanen (I) werden nach dem Malonester‐Verfahren die (z.T.

Cited by 2 publications

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New GM1 Ganglioside Derivatives for Selective Single and Double Labelling of the Natural Glycosphingolipid Skeleton

New GM1 Ganglioside Derivatives for Selective Single and Double Labelling of the Natural Glycosphingolipid Skeleton

Fluorescent and Photochromic Fluorescent Compounds for Applications in Optical Nanoscopy

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