Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains
This paper describes the synthesis of two 6-azido-6-deoxy derivatives of phosphatidylinositol (PI), which contained different fatty acid chains. These syntheses, starting from methyl α-d-glucopyranoside, employed multiple regioselective transformations with Ferrier rearrangement as one of the key st...
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| Language: | English |
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MDPI AG
2024-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/21/4981 |
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| author | Mosidur Rahaman Molla Palak Gupta Rajendra Rohokale Zhongwu Guo |
| author_facet | Mosidur Rahaman Molla Palak Gupta Rajendra Rohokale Zhongwu Guo |
| author_sort | Mosidur Rahaman Molla |
| collection | DOAJ |
| description | This paper describes the synthesis of two 6-azido-6-deoxy derivatives of phosphatidylinositol (PI), which contained different fatty acid chains. These syntheses, starting from methyl α-d-glucopyranoside, employed multiple regioselective transformations with Ferrier rearrangement as one of the key steps. The PI derivatives contained different fatty acid chains in the lipids and an azido group in the inositol residue to facilitate their further functionalization under bioorthogonal conditions. Therefore, they should be useful probes for the investigation of PI and related biology, such as PI phosphorylation, PI interaction with other molecules in cells, and the functions of lipid structures in these processes. |
| format | Article |
| id | doaj-art-d2c334c3dad24f8aaa79600daf4b3b6e |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-d2c334c3dad24f8aaa79600daf4b3b6e2025-08-20T02:13:18ZengMDPI AGMolecules1420-30492024-10-012921498110.3390/molecules29214981Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid ChainsMosidur Rahaman Molla0Palak Gupta1Rajendra Rohokale2Zhongwu Guo3Department of Chemistry, University of Florida, Gainesville, FL 32611, USADepartment of Chemistry, University of Florida, Gainesville, FL 32611, USADepartment of Chemistry, University of Florida, Gainesville, FL 32611, USADepartment of Chemistry, University of Florida, Gainesville, FL 32611, USAThis paper describes the synthesis of two 6-azido-6-deoxy derivatives of phosphatidylinositol (PI), which contained different fatty acid chains. These syntheses, starting from methyl α-d-glucopyranoside, employed multiple regioselective transformations with Ferrier rearrangement as one of the key steps. The PI derivatives contained different fatty acid chains in the lipids and an azido group in the inositol residue to facilitate their further functionalization under bioorthogonal conditions. Therefore, they should be useful probes for the investigation of PI and related biology, such as PI phosphorylation, PI interaction with other molecules in cells, and the functions of lipid structures in these processes.https://www.mdpi.com/1420-3049/29/21/4981azideglycolipidglycosylphosphatidylinositolinositolphosphatidylinositol |
| spellingShingle | Mosidur Rahaman Molla Palak Gupta Rajendra Rohokale Zhongwu Guo Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains Molecules azide glycolipid glycosylphosphatidylinositol inositol phosphatidylinositol |
| title | Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains |
| title_full | Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains |
| title_fullStr | Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains |
| title_full_unstemmed | Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains |
| title_short | Chemical Synthesis of 6-Azido-6-Deoxy Derivatives of Phosphatidylinositol Containing Different Fatty Acid Chains |
| title_sort | chemical synthesis of 6 azido 6 deoxy derivatives of phosphatidylinositol containing different fatty acid chains |
| topic | azide glycolipid glycosylphosphatidylinositol inositol phosphatidylinositol |
| url | https://www.mdpi.com/1420-3049/29/21/4981 |
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