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Two novel 23-fluorinated 25-hydroxyvitamin D 3 analogues were synthesized using Inhoffen-Lythgoe diol as a precursor of the CD-ring, efficiently. Introduction of the C23 fluoro group was achieved by the deoxy-fluorination reaction using N , N -diethylaminosulfur trifluoride or 2-pyridinesulfonyl fluoride (PyFluor). Kinetic studies on the CYP24A1-dependent metabolism of these two analogues revealed that (23 S )-23-fluoro-25-hydroxyvitamin D 3 was more resistant to CYP24A1-dependent metabolism than its 23 R isomer.

Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D3 Analogues

Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D₃ Analogues