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Studying Lipophilicity Trends of Phosphorus Compounds by ^31^P-NMR Spectroscopy: A Powerful Tool for the Design of P-Containing Drugs by Ishay Columbus; Lee Ghindes-Azaria; Ravit Chen; Lea Yehezkel; Orit Redy-Keisar; Gil Fridkin; Dafna Amir; Daniele Marciano; Eyal Drug; Eytan Gershonov; Ziv Klausner; Sigal Saphier; Shlomi Elias; Alexander Pevzner; Yoav Eichen; Galit Parvari; Boris Smolkin; Yossi Zafrani is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.
What is Studying Lipophilicity Trends of Phosphorus Compounds by ^31^P-NMR Spectroscopy: A Powerful Tool for the Design of P-Containing Drugs about?
Systematically studying the lipophilicity of phosphorus compounds is of great importance for many chemical and biological fields and particularly for medicinal chemistry. Here, we report on the study of trends in the lipophilicity of a wide set of phosphorus compounds relevant to drug design including phosphates, thiophosphates, phosphonates, thiophosphonates, bis-phosphonates, and phosphine chalcogenides. This was enabled by the development of a straightforward log P determination method for phosphorus compounds based on 31 P-NMR spectroscopy. The log P values measured ranged between −3.2 and 3.6, and the trends observed were interpreted using a DFT study of the dipole moments and by H-bond basicity (pK HB ) measurements of selected compounds. Clear signal separation in 31 P-NMR spectroscopy grants the method high tolerability to impurities. Moreover, the wide range of chemical shifts for the phosphorus nucleus (250 to −250 ppm) enables a direct simultaneous log P determination of phosphorus compound mixtures in a single shake-flask experiment and 31 P-NMR analysis.
Who reads Studying Lipophilicity Trends of Phosphorus Compounds by ^31^P-NMR Spectroscopy: A Powerful Tool for the Design of P-Containing Drugs?
It is typically read by researchers, students, and practitioners in Biochemistry, Genetics and Molecular Biology.
- Author
- Ishay Columbus; Lee Ghindes-Azaria; Ravit Chen; Lea Yehezkel; Orit Redy-Keisar; Gil Fridkin; Dafna Amir; Daniele Marciano; Eyal Drug; Eytan Gershonov; Ziv Klausner; Sigal Saphier; Shlomi Elias; Alexander Pevzner; Yoav Eichen; Galit Parvari; Boris Smolkin; Yossi Zafrani
- Publisher
- American Chemical Society (ACS)
- Published
- 2022
- Language
- EN
- Field
- Biochemistry, Genetics and Molecular Biology (Life Sciences)