Efficient assembly of threaded molecular machines for sequence-specific synthesis

J Am Chem Soc. 2014 Apr 16;136(15):5811-4. doi: 10.1021/ja5022415. Epub 2014 Apr 7.

Abstract

We report on an improved strategy for the preparation of artificial molecular machines that can pick up and assemble reactive groups in sequence by traveling along a track. In the new approach a preformed rotaxane synthon is attached to the end of an otherwise fully formed strand of building blocks. This "rotaxane-capping" protocol is significantly more efficient than the "final-step-threading" method employed previously and enables the synthesis of threaded molecular machines that operate on extended oligomer, and potentially polymer, tracks. The methodology is exemplified through the preparation of a machine that adds four amino acid building blocks from a strand in sequence, featuring up to 20-membered ring native chemical ligation transition states.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Peptide Mapping
  • Rotaxanes / chemistry*
  • Tandem Mass Spectrometry

Substances

  • Rotaxanes