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An efficient, scalable synthesis of the molecular transporter octaarginine via a segment doubling strategy
P A Wender1, T C Jessop, K Pattabiraman
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@leland.stanford.edu
Organic Letters
|October 12, 2001
Abstract:
[reaction: see text]. 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.