Synthesis of potentially caged sphingolipids, possible precursors of cellular modulators and second messengers

Chemistry and Physics of Lipids
U Zehavi

Abstract

An increasing number of sphingolipids, glycosphingolipids and some of their degradation products have been recognized in recent years as second messengers involved in signal transduction and as modulators of numerous cellular functions. These can be converted into inert, caged compounds, introduced into cells and tissues and subsequently photolysed to active compounds thus enabling the study of fast biological processes. The novel, potentially caged compounds synthesized here are substituted 2-nitrobenzyl urethans and 2-nitrobenzyl amines derived from sphingosine, dihydrosphingosine, N-methylsphingosine, N-methyldihydrosphingosine, psychosine and glucosylsphingosine. Upon irradiation of the afore mentioned compounds they release, or are expected to release, the free biologically active amines.

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Citations

Nov 17, 2009·The Journal of Organic Chemistry·Ravi S LankalapalliRobert Bittman
Jul 6, 2000·The Biochemical Journal·S Pyne, N J Pyne
Apr 10, 2014·Biochimica Et Biophysica Acta·Doris HöglingerCarsten Schultz
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo

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