Synthesis and transmembrane transport studies by NMR of a glucosyl phospholipid of thymidine
A phosphotriester derivative of thymidine, glucose, and hexadecanol was prepared by the nucleophilic displacement of 1-bromohexadecane by 6-glucopyranosyl 5'-thymidinyl phosphate. This compound was synthesized as a model of a transport molecule related to dolichyl 1-glucose phosphate. Its struc...
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| Veröffentlicht in: | Journal of the American Chemical Society 1989-06, Vol.111 (12), p.4270-4277 |
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| container_end_page | 4277 |
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| container_issue | 12 |
| container_start_page | 4270 |
| container_title | Journal of the American Chemical Society |
| container_volume | 111 |
| creator | Neumann, Jean Michel Herve, Martine Debouzy, Jean Claude Iglesias Guerra, Fernando Gouyette, Catherine Dupraz, Bernadette Huynh Dinh Tam |
| description | A phosphotriester derivative of thymidine, glucose, and hexadecanol was prepared by the nucleophilic displacement of 1-bromohexadecane by 6-glucopyranosyl 5'-thymidinyl phosphate. This compound was synthesized as a model of a transport molecule related to dolichyl 1-glucose phosphate. Its structure and interaction with large unilamellar vesicles were studied by super(1)H, super(13)C, and super(31)P NMR spectroscopy: the detection of the phosphotriester of thymidine inside the vesicles implied its transfer across the lipid bilayer, in contrast with its phosphodiester precursors which either did not interact with the membrane or alter the lipid layer. |
| doi_str_mv | 10.1021/ja00194a018 |
| format | Article |
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This compound was synthesized as a model of a transport molecule related to dolichyl 1-glucose phosphate. Its structure and interaction with large unilamellar vesicles were studied by super(1)H, super(13)C, and super(31)P NMR spectroscopy: the detection of the phosphotriester of thymidine inside the vesicles implied its transfer across the lipid bilayer, in contrast with its phosphodiester precursors which either did not interact with the membrane or alter the lipid layer.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja00194a018</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Cell physiology ; Fundamental and applied biological sciences. 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Am. Chem. Soc</addtitle><date>1989-06-01</date><risdate>1989</risdate><volume>111</volume><issue>12</issue><spage>4270</spage><epage>4277</epage><pages>4270-4277</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A phosphotriester derivative of thymidine, glucose, and hexadecanol was prepared by the nucleophilic displacement of 1-bromohexadecane by 6-glucopyranosyl 5'-thymidinyl phosphate. This compound was synthesized as a model of a transport molecule related to dolichyl 1-glucose phosphate. 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| ispartof | Journal of the American Chemical Society, 1989-06, Vol.111 (12), p.4270-4277 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | American Chemical Society Journals |
| subjects | Biological and medical sciences Cell physiology Fundamental and applied biological sciences. Psychology Membrane and intracellular transports membrane vesicles Molecular and cellular biology N.M.R |
| title | Synthesis and transmembrane transport studies by NMR of a glucosyl phospholipid of thymidine |
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