An Efficient, Scalable Synthesis of the Molecular Transporter Octaarginine via a Segment Doubling Strategy

Autor: Wender, P. A., Jessop, T. C., Pattabiraman, K., Pelkey, E. T., VanDeusen, C. L.
Zdroj: Organic Letters; October 2001, Vol. 3 Issue: 21 p3229-3232, 4p
Abstrakt: Short oligomers of arginine function as remarkably efficient molecular transporters of drugs and probe molecules into cells and tissue. Currently, these compounds are prepared on resin through a unidirectional solid-phase synthesis. To extend the utility of these compounds for therapeutic and research applications, a scalable solution-phase synthesis of Arg8 (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 perdeprotection−perguanidinylation reaction.
Databáze: Supplemental Index