PHOSPHORYLATION OF POLYPRENOLS BY THE 1,3,2-DIOXAPHOSPHORINANE DERIVATIVES
Abstract
Phosphorylation of polyprenols by chloro- and amidocyclophosphites on hydroxyl group was studied. Phosphocyclophosphites , phosphates and thiophosphates of polyprenol were obtained and chromotographically isolated. It was shown that they are formed as conformers and cis-trans isomers. With the aim of obtaining original homocholines, which exist in thiono- and thioloforms, the alkylation of trimethylamine by polyprenyl-2-thio-1,3,2-dioxaphosphorinane were performed, but we failed to separate thiono- and thioloforms. The ammonium salt as thionoform was obtained by the hydrolysis of the same thiophosphate in the presence of triethylamine. The structures of all synthesized substances were proved by NMR 1H, 13C and 31P spectroscopy with using of homo-decoupling magnetic resonance and 2D-correlated spectroscopy HETCOR 1H- 13CDownloads
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Санин А.В., Ганшина И.В., Судьина Г.Ф., Санина В.Ю., Кожевникова Т.Н., Пронин А.В., Наровлянский А.Н., Суханов С.А., Проскурина О.В., Митрохин Н.М. Фосфорилированные полипренолы – новый класс соедине-ний с противовоспалительной и бронхолитической активностью // Инфекция и иммунитет. 2011. Т. 1, №4. С. 355–360.
Чернова С.И., Пронин А.В., Наровлянский А.Н., Санин А. В. Воспалительные процессы в эволюции атеро-склероза и их коррекция полиизопреноидами // Терапевт. 2012. №4. С. 15–22.
Расадкина Е.Н., Маленковская М.А., Пугашова Н.М., Нифантьев Э.Е. Фосфорилирование полипренолов ами-дами фосфористой кислоты // Химия растительного сырья. 2012. №2. С. 69–72.
Нифантьев Э. E., Завалишина А. И. Успехи химии 1,3,2-дигетерофосфор(III)инанов // Успехи химии. 1982. Т. 51, вып. 10. С. 1601–1637.
Miller A.D. Cationic Liposomes for Gene Therapy // Angew.Chem. 1998. Vol. 37, N13/14. Рp. 1768–1785.
Маслов М.А., Сычева Е.В., Морозова Н.К., Серебренникова Г.А. Катионные амфифилы липидной и нелипид-ной природы в генной терапии // Известия РАН. Сер. хим. 2000. №3. С. 385–400.
Nifantyev E.E., Predvoditelev D.A., Rasadkina E.N., Bekker A.R. Synthesis of 1,2-O-isopropylidene glycerol-thiolo-(dithiolo)phosphohomocholines. A new thion-thiol isomerization of alkylene phosphorothioates // Phosphorus and Sulfur. 1987. Vol. 34. Pp. 109–117.
Нифантьев Э.Е., Завалишина А.И. Химия элементоорганических соединений: спецпрактикум. М., 1980. С. 47–58.
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