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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2024-10, Vol.29 (21), p.4981
Main Authors: Molla, Mosidur Rahaman, Gupta, Palak, Rohokale, Rajendra, Guo, Zhongwu
Format: Article
Language:English
Subjects:
Azide
Azides - chemistry
Biosynthesis
Chemical synthesis
Chromatography
Design
Fatty acids
Fatty Acids - chemical synthesis
Fatty Acids - chemistry
glycolipid
glycosylphosphatidylinositol
Inositol
Lipids
Metabolism
Molecular Structure
phosphatidylinositol
Phosphatidylinositols - chemical synthesis
Phosphatidylinositols - chemistry
Phospholipids
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29214981