Synthesis of structurally diverse bis-peptide oligomers.
We have developed second-generation monomers 1 and 2 and improved conditions for rapidly and simultaneously closing multiple diketopiperazines on solid support. These new conditions involve either the microwave heating of a suspension of solid-supported amino-tetrafluoropropyl esters in acetic acid/triethylamine catalyst solution or continuous flow of catalyst solution through the resin, heated in a flow cell apparatus. We demonstrate that the new monomers 1 and 2 can be combined with the new conditions easily to synthesize previously inaccessible hetero and homo spiro ladder oligomers 3 and 4 and others.
Gupta
Sharad
S
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Macala
Megan
M
Schafmeister
Christian E
CE
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D008872:Microwaves; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D011487:Protein Conformation; D013237:Stereoisomerism
D009842:Oligopeptides; D010879:Piperazines