含氟甾体的固态核磁共振研究。
Solid-state NMR study of fluorinated steroids.
作者信息
Yang Kai-Jay, Lin Su-Ching, Huang Shing-Jong, Ching Wei-Min, Hung Chen-Hsiung, Tzou Der-Lii M
机构信息
Institute of Chemistry, Academia Sinica, Nankang, Taipei 11529, Taiwan, ROC.
Instrumentation Center, National Taiwan University, Taipei 11617, Taiwan, ROC.
出版信息
Steroids. 2014 Feb;80:64-70. doi: 10.1016/j.steroids.2013.11.020. Epub 2013 Dec 6.
Solid-state {(1)H}(13)C cross-polarization/magic angle spinning (CP/MAS) NMR spectroscopy was performed to analyze two fluorinated steroids, i.e., betamethasone (BMS) and fludrocortisone acetate (FCA), that have fluorine attached to C9, as well as two non-fluorinated analogs, i.e., prednisolone (PRD) and hydrocortisone 21-acetate (HCA). The (13)C signals of BMS revealed multiplet patterns with splittings of 16-215Hz, indicating multiple ring conformations, whereas the (13)C signals of FCA, HCA, and PRD exhibited only singlet patterns, implying a unique conformation. In addition, BMS and FCA exhibited substantial deviation (>3.5ppm) in approximately half of the (13)C signals and significant deviation (>45ppm) in the (13)C9 signal compared to PRD and HCA, respectively. In this study, we demonstrate that fluorinated steroids, such as BMS and FCA, have steroidal ring conformation(s) that are distinct from non-fluorinated analogs, such as PRD and HCA.
采用固态{¹H}¹³C交叉极化/魔角旋转（CP/MAS）核磁共振波谱法分析了两种在C9位连接有氟原子的氟化甾体，即倍他米松（BMS）和醋酸氟氢可的松（FCA），以及两种非氟化类似物，即泼尼松龙（PRD）和醋酸氢化可的松（HCA）。BMS的¹³C信号显示出多重峰模式，分裂为16 - 215Hz，表明存在多种环构象，而FCA、HCA和PRD的¹³C信号仅呈现单峰模式，这意味着构象独特。此外，与PRD和HCA相比，BMS和FCA分别在大约一半的¹³C信号中表现出显著偏差（>3.5ppm），在¹³C9信号中表现出明显偏差（>45ppm）。在本研究中，我们证明了氟化甾体，如BMS和FCA，具有与非氟化类似物，如PRD和HCA不同的甾体环构象。
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