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A small-molecule walker ratcheted by enzymatic hydrolysis

This work describes the design, synthesis and operation of a (R,R)-(+)-hydrobenzoin-diacetic acid molecular walker attached to polyether tracks containing 2, 3 or 4 secondary alcohol footholds. A macrocycle-the walker attached to a 2-foothold track by two ester linkages-was regioselectively hydrolysed by lipase AS. The resultant seco¬-acid was recyclised using Yamaguchi chemistry, demonstrating a bipedal walker stepping off, and on to, a track. These conditions were extended to tracks containing 3 and 4 alcohol footholds and the design of a 3-foothold track that incorporated a pentaethylene glycol chain. Using an information type Brownian ratchet mechanism, ~90% of walkers stepped away from the starting position, and ~68% of walkers took 2 steps to a foothold 16 atoms away. Importantly only smaller or equal to4% of walkers were found to completely detach from the track per operation cycle.

Identiferoai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:728199
Date January 2017
CreatorsMartin, Christopher
ContributorsLeigh, David
PublisherUniversity of Manchester
Source SetsEthos UK
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Sourcehttps://www.research.manchester.ac.uk/portal/en/theses/a-smallmolecule-walker-ratcheted-by-enzymatic-hydrolysis(3cfb64ba-9959-46e8-937b-14c712c92970).html

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