TY - JOUR
T1 - Production of ..beta..-Ketoadipic Acid from Glucose in Pseudomonas putida KT2440 for Use in Performance-Advantaged Nylons
AU - Rorrer, Nicholas
AU - Notonier, Sandra
AU - Knott, Brandon
AU - Black, Brenna
AU - Singh, Avantika
AU - Nicholson, Scott
AU - Kinchin, Christopher
AU - Schmidt, Graham
AU - Carpenter, Alberta
AU - Ramirez, Kelsey
AU - Johnson, Christopher
AU - Salvachua, Davinia
AU - Crowley, Michael
AU - Beckham, Gregg
N1 - Publisher Copyright:
© 2022 The Author(s)
PY - 2022/4/20
Y1 - 2022/4/20
N2 - Biomass-derived chemicals can offer unique chemical functionality relative to petroleum-derived building blocks. To this end, here we report that β-ketoadipic acid (βKA), a C6 diacid with a β-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, Pseudomonas putida KT2440 is engineered to produce βKA from glucose, achieving a 26 g/L titer. Following purification, βKA imparts an increase of 69°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 β-ketone. Process analysis predicts that βKA 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 βKA to serve as a useful building block for bio-based polymers.
AB - Biomass-derived chemicals can offer unique chemical functionality relative to petroleum-derived building blocks. To this end, here we report that β-ketoadipic acid (βKA), a C6 diacid with a β-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, Pseudomonas putida KT2440 is engineered to produce βKA from glucose, achieving a 26 g/L titer. Following purification, βKA imparts an increase of 69°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 β-ketone. Process analysis predicts that βKA 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 βKA to serve as a useful building block for bio-based polymers.
KW - biopolymer
KW - bioprivileged molecule
KW - bioproduct
KW - metabolic engineering
KW - molecular dynamics
KW - nylon
KW - polyamide
UR - http://www.scopus.com/inward/record.url?scp=85128418395&partnerID=8YFLogxK
U2 - 10.1016/j.xcrp.2022.100840
DO - 10.1016/j.xcrp.2022.100840
M3 - Article
AN - SCOPUS:85128418395
SN - 2666-3864
VL - 3
JO - Cell Reports Physical Science
JF - Cell Reports Physical Science
IS - 4
M1 - Article No. 100840
ER -