Sequence-defined polymers via orthogonal allyl acrylamide building blocks

J Am Chem Soc. 2014 Sep 24;136(38):13162-5. doi: 10.1021/ja507262t. Epub 2014 Sep 16.

Abstract

Biological systems have long recognized the importance of macromolecular diversity and have evolved efficient processes for the rapid synthesis of sequence-defined biopolymers. However, achieving sequence control via synthetic methods has proven to be a difficult challenge. Herein we describe efforts to circumvent this difficulty via the use of orthogonal allyl acrylamide building blocks and a liquid-phase fluorous support for the de novo design and synthesis of sequence-specific polymers. We demonstrate proof-of-concept via synthesis and characterization of two sequence-isomeric 10-mer polymers. (1)H NMR and LCMS were used to confirm their chemical structure while tandem MS was used to confirm sequence identity. Further validation of this methodology was provided via the successful synthesis of a sequence-specific 16-mer polymer incorporating nine different monomers. This strategy thus shows promise as an efficient approach for the assembly of sequence-specific functional polymers.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acrylamide / chemical synthesis
  • Acrylamide / chemistry*
  • Allyl Compounds / chemical synthesis
  • Allyl Compounds / chemistry*
  • Halogenation
  • Models, Molecular
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry

Substances

  • Allyl Compounds
  • Polymers
  • Sulfhydryl Compounds
  • Acrylamide