Sequence-Defined Oligomers from Hydroxyproline Building Blocks for Parallel Synthesis Applications
Name
nihms835873.pdf
Description
Accepted version
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876.62 KB
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Author(s)
Kanasty, Rosemary Lynn
Vegas, Arturo
Ceo, Luke
Maier, Martin
Charisse, Klaus
Nair, Jayaprakash K.
Langer, Robert S
Anderson, Daniel Griffith
Date Issued
July 2016
Journal
Angewandte Chemie International Edition
Publisher
Wiley
Citation
Kanasty, Rosemary et al. "Sequence‐Defined Oligomers from Hydroxyproline Building Blocks for Parallel Synthesis Applications." Angewandte Chemie International Edition 55, 33 (July 2016): 9529-9533 © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Version
Author's final manuscript
Abstract
The functionality of natural biopolymers has inspired significant effort to develop sequence-defined synthetic polymers for applications including molecular recognition, self-assembly, and catalysis. Conjugation of synthetic materials to biomacromolecules has played an increasingly important role in drug delivery and biomaterials. We developed a controlled synthesis of novel oligomers from hydroxyproline-based building blocks and conjugated these materials to siRNA. Hydroxyproline-based monomers enable the incorporation of broad structural diversity into defined polymer chains. Using a perfluorocarbon purification handle, we were able to purify diverse oligomers through a single solid-phase extraction method. The efficiency of synthesis was demonstrated by building 14 unique trimers and 4 hexamers from 6 diverse building blocks. We then adapted this method to the parallel synthesis of hundreds of materials in 96-well plates. This strategy provides a platform for the screening of libraries of modified biomolecules. Keywords: bioconjugates; fluorous synthesis; oligomers; sequence-defined polymers; siRNA
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Biological Engineering
Harvard University--MIT Division of Health Sciences and Technology
Massachusetts Institute of Technology. Institute for Medical Engineering & Science
Koch Institute for Integrative Cancer Research at MIT
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DOI of Published Version
https://doi.org/10.1002/anie.201602748
