Near-Quantitative
Aqueous Synthesis of Rotaxanes via
Bioconjugation to Oligopeptides and Proteins
Carson
J. Bruns
Hanwei Liu
Matthew B. Francis
10.1021/jacs.6b10231.s001
https://acs.figshare.com/articles/journal_contribution/Near-Quantitative_Aqueous_Synthesis_of_Rotaxanes_via_Bioconjugation_to_Oligopeptides_and_Proteins/4235756
In spite of widespread
interest in rotaxane-based molecular machines
and materials, rotaxanes have not been attached covalently to proteins.
We describe the near-quantitative aqueous synthesis of [2]rotaxanes
based on neutral and charged aqueous hostscucurbit[7]uril
(CB7) and cyclobis(paraquat-<i>p</i>-phenylene) (CBPQT<sup>4+</sup>), respectivelyusing the thiol-ene addition of cysteine
and maleimide as a stoppering protocol. After verifying the high efficiency
of the reaction using glutathione (GSH) as an oligopeptide stopper,
we have employed cytochrome C (CytC) as a protein stopper to produce
the first well-characterized protein-rotaxane bioconjugates. We anticipate
that this methodology will enable the preparation of novel materials
that combine the unique properties of proteins and mechanical bonds.
2016-11-08 00:00:00
well-characterized protein-rotaxane bioconjugates
stoppering protocol
cytochrome C
Near-Quantitative Aqueous Synthesis
CBPQT
thiol-ene addition
novel materials
CB
protein stopper
oligopeptide stopper
GSH