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Sequence-Defined Oligomers from Hydroxyproline Building Blocks for Parallel Synthesis Applications.


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.

SUBMITTER: Kanasty RL 

PROVIDER: S-EPMC5245870 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Sequence-Defined Oligomers from Hydroxyproline Building Blocks for Parallel Synthesis Applications.

Kanasty Rosemary L RL   Vegas Arturo J AJ   Ceo Luke M LM   Maier Martin M   Charisse Klaus K   Nair Jayaprakash K JK   Langer Robert R   Anderson Daniel G DG  

Angewandte Chemie (International ed. in English) 20160701 33


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  ...[more]

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