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Title: A small-molecule walker ratcheted by enzymatic hydrolysis
Author: Martin, Christopher
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2017
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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.
Supervisor: Leigh, David Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: directional ; processive ; lipase AS ; molecular machine ; ratchet ; walker ; enzyme