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Efficient assembly of threaded molecular machines for sequence-specific synthesis.

Journal of the American Chemical Society (2014-04-01)
Guillaume De Bo, Sonja Kuschel, David A Leigh, Bartosz Lewandowski, Marcus Papmeyer, John W Ward
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.