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