Department of Chemistry, University of Florida, Gainesville, FL 32611, USA.
UF Health Cancer Center, University of Florida, Gainesville, FL 32611, USA.
Molecules. 2024 Oct 22;29(21):4981. doi: 10.3390/molecules29214981.
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.
本文描述了两种含有不同脂肪酸链的 6-叠氮基-6-去氧磷脂酰肌醇（PI）衍生物的合成。这些合成以甲基 α-d-吡喃葡萄糖苷为起始原料，通过多次区域选择性转化，其中 Ferrier 重排是关键步骤之一。PI 衍生物在脂质部分含有不同的脂肪酸链，在肌醇残基中含有叠氮基团，以便在生物正交条件下进一步进行功能化。因此，它们应该是研究 PI 和相关生物学的有用探针，例如 PI 磷酸化、PI 与细胞中其他分子的相互作用，以及这些过程中脂质结构的功能。
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