Bi-directional synthesis of oligoguanidine transport agents
AssigneeThe Board of Trustees of the Leland Stanford Junior University
InventorsPaul A. Wender, Christopher L. VanDeusen, Kanaka Pattabiraman, Erin T. Pelkey, Theodore C. Jessop
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Abstract
Synthesis routes that can be adapted to large scale synthesis of oligoguanidine compounds such as oligoarginine compounds are described which use a perguanidinylation step to convert a group of ω-amino groups to the corresponding guanidinyl groups. These compounds find utility as transport agents. Modified oligoguanidine compounds are also described.
Claims30
A method for the preparation of an oligoguanidine compound, comprising:
- (a) contacting an oligomer having a plurality of chemically tethered amines, wherein a portion of said tethered amines have attached protecting groups, with a protecting group removal agent to remove said protecting groups to produce an oligomer having a plurality of chemically tethered amines;
- and
- (b) contacting said oligomer having a plurality of chemically tethered amines with a salt of pyrazole-1-carboxamidine to convert each of said chemically tethered amines to a guanidinyl group to produce an oligoguanidine compound;
- wherein the contacting of steps (a) and (b) is carried out in solution.
The method of claim 22, wherein the oligoguanidine compound has the formula (X0-Arg-X0)q.
Dependencies are inferred from the claim text.