Biomass-derived chemicals can offer unique chemical functionality relative to petroleum-derived building blocks. To this end, here we report that ?-ketoadipic acid (?KA), a C6 diacid with a ?-ketone group, can be used as a performance-advantaged replacement for adipic acid in a nylon-6,6 analog. Building on our previous efforts to produce shikimate-derived products from carbohydrates, <
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KT2440 is engineered to produce ?KA from glucose, achieving a 26 g/L titer. Following purification, ?KA imparts an increase of 69 degrees C above the nylon-6,6 glass transition temperature and 20% reduced water permeability, equivalent to nylon-6,10. Molecular simulations predict that the enhanced thermal properties result from rigidity introduced by the ?-ketone. Process analysis predicts that ?KA can be produced for US$1.94/kg from sugars, requiring 63% less energy and emitting 43% less greenhouse gases than fossil-based adipic acid. Overall, this study illustrates the potential for ?KA to serve as a useful building block for bio-based polymers.