American Chemical Society
jo0609125_si_001.pdf (1.95 MB)

Synthesis of Structurally Diverse Bis-peptide Oligomers

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journal contribution
posted on 2006-11-10, 00:00 authored by Sharad Gupta, Megan Macala, Christian E. Schafmeister
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.