An efficient, scalable synthesis of the molecular transporter octaarginine via a segment doubling strategy.
[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.
Wender
P A
PA
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@leland.stanford.edu
Jessop
T C
TC
Pattabiraman
K
K
Pelkey
E T
ET
VanDeusen
C L
CL
D001120:Arginine / Q000737:chemistry*; D004337:Drug Carriers / Q000138:chemical synthesis*; D015335:Molecular Probes / Q000138:chemical synthesis; D009842:Oligopeptides / Q000138:chemical synthesis*
D004337:Drug Carriers; D015335:Molecular Probes; D009842:Oligopeptides; C448619:octaarginine; D001120:Arginine