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Updated: Oct 5, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Solid-phase library synthesis of alkoxyprolines
A M Boldi1, J M Dener, T P Hopkins
1ChemRx Advanced Technologies, Inc., A Discovery Partners International Company, 385 Oyster Point Boulevard, Suite 1, South San Francisco, California 94080, USA.
Abstract:
The library synthesis of alkoxyprolines was achieved using an acid-stable, nucleophile-cleavable solid support. A hydroxythiophenol linker derived from Merrifield resin was esterified with the corresponding ethers of BOC-hydroxyproline. Removal of the BOC protecting group with trifluoroacetic acid followed by acylation gave solid-supported hydroxyproline derivatives. Cleavage from the solid support with excess primary amines or excess secondary amines followed by purification of the crude products from the excess amine by supported liquid-liquid extraction gave the alkoxyproline library in high purity.
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