Spermine (Sp)

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, in particular, in viruses. Crystals of spermine phosphate were first described in 1678, in human semen, by Anton van Leeuwenhoek.The utility of spermine, selectively functionalised and immobilised on a solid support by means of the Wang "oxycarbonyl" linker is demonstrated by the solid-phase synthesis of a number of spermine conjugates including the natural product and potent antihypertensive agent kukoamine. The synthesis opens up the area of solid-phase spermine chemistry and library generation based on the symmetrical spermine scaffold.