An efficient, scalable synthesis of the molecular transporter octaargininevia a segment doubling strategy

[GRAPHICS] Short oligomers of arginine function as remarkably efficient molecular tran sporters of drugs and probe molecules into cells and tissue. Currently, the se compounds are prepared on resin through a unidirectional solid-phase syn thesis. To extend the utility of these compounds for therapeutic and resear ch applications, a scalable solution-phase synthesis of Arg(8) (1) has been developed on the basis of a segment doubling strategy that proceeds in 13 steps and 28% overall yield from 4, including a novel one-step perdeprotect ion-perguanidinylation reaction.