Synthesis, Table of Contents Synthesis 2024; 56(11): 1787-1792DOI: 10.1055/a-2257-0684 paper A Convenient Method for Synthesizing 1-Alkyl-2-acyl-sn-glycero-3-phosphoethanolamines Tatsuo Okauchi ∗ , Kouta Tsubaki , Yuri Higuma , Hirokazu Shimooka , Mitsuru Kitamura Recommend Article Abstract Buy Article All articles of this category Dedicated to Professor Koichi Narasaka in celebration of his 80th birthday (Sanju) Abstract A convenient method for synthesizing 1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamines (1-alkyl-2-acyl-GPEs) starting from an optical active alcohol is described. In this method, the phosphate group was introduced through the transesterification that we developed, and a protected 1-alkyl-2-lyso-GPE was employed as an intermediate. This compound is stable and serves as a common intermediate for the synthesis of various 1-alkyl-2-acyl-GPEs with different acyl groups. Key words Key wordsether phospholipids - glycerophospholipids - phosphoethanolamines - transesterification - phosphorylation Full Text References References 1a Dean JM, Lodhi IJ. Protein Cell 2018; 9: 196 1b Jiménez-Rojo N, Riezman H. FEBS Lett. 2019; 593: 2378 2a Kostadinova A, Topouzova-Hristova T, Momchilova A, Tzoneva R, Berger MR. Antitumor Lipids–Structure, Functions, and Medical Applications. In Advances in Protein Chemistry and Structural Biology, Vol. 101. Donev R. Academic Press; London: 2015: 27-66 2b van Blitterswijk JW, Verheij M. Curr. Pharm. Des. 2008; 14: 2061 3 Paltauf F. Chem. Phys. Lipids 1994; 74: 101 4 Marathe GK, Chaithra VH, Ke L.-Y, Chen C.-H. Prostaglandins Other Lipid Mediators 2020; 151: 106478 5a Zhu G, Alhamhoom Y, Cummings BS, Arnold RD. Bioorg. Med. Chem. Lett. 2011; 21: 6370 5b Derksen JT, Baldeschwieler JD, Scherphof GL. Proc. Natl. Acad. Sci. U. S. A. 1988; 85: 9768 6a Wichmann O, Gelb MH, Schultz C. ChemBioChem 2007; 8: 1555 6b Peters GH, Møller MS, Jørgensen K, Rönnholm P, Mikkelsen M, Andresen TL. J. Am. Chem. Soc. 2007; 129: 5451 6c Moghimi SM, Hamad I, Andresen TL, Jørgensen K, Szebeni J. FASEB J. 2006; 20: 2591 6d Spyvee MR, Zhang H, Hawkins LD, Chow JC. Bioorg. Med. Chem. Lett. 2005; 15: 5494 6e Xia J, Hui Y.-Z. Tetrahedron: Asymmetry 1997; 8: 3131 7a Tsubaki K, Yamanaka T, Hisamitsu T, Shimooka H, Kitamura M, Okauchi T. Synthesis 2021; 53: 3827 7b Tsubaki K, Shimooka H, Kitamura M, Okauchi T. Org. Lett. 2019; 21: 9779 8 Purification of Laboratory Chemicals, 5th ed. Armarego WL. F, Chai CL. L. Butterworth-Heinemann; London: 2002 9 Tsubaki K. Development and applications of a new synthetic method for the synthesis of organophosphate. Kyushu Institute of Technology, Faculty of Engineering, Department of Applied Chemistry, Ph.D. Thesis, Kitakyushu (Japan), 2021, https://kyutech.repo.nii.ac.jp/records/7134. 10 Gil-Mesón A, Roncero AM, Tobal IE, Basabe P, Díez D, Mollinedo F, Marcos IS. Molecules 2016; 21: 47 Supplementary Material Supplementary Material Supporting Information
