Mechanistic investigation of enzymatic degradation of polyethylene terephthalate by nuclear magnetic resonance

Austin, 2018, Characterization and engineering of a plastic-degrading aromatic polyesterase, Proceedings of the National Academy of Sciences of the United States of America, 115, E4350 Bak, 2000, SIMPSON: A general simulation program for solid-state NMR spectroscopy, Journal of Magnetic Resonance, 147, 296, 10.1006/jmre.2000.2179 Banerjee, 2015, Two-dimensional nuclear magnetic resonance: Exploiting spin echoes to maximize information content by suppression of diagonal peaks in homonuclear experiments, The Journal of Physical Chemistry A, 119, 482, 10.1021/jp512511h Becke, 1988, Density-functional exchange-energy approximation with correct asymptotic behavior, Physical Review A, 38, 3098, 10.1103/PhysRevA.38.3098 Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange, The Journal of Chemical Physics, 98, 5648, 10.1063/1.464913 Berkowitz, 1984, Viscosity–molecular weight relationships for poly(ethylene terephthalate) in hexafluoroisopropanol–pentafluorophenol using SEC–LALLS, Journal of Applied Polymer Science, 29, 4353, 10.1002/app.1984.070291264 Chan, 2003, Recoupling of chemical shift anisotropies in solid-state NMR under high-speed magic-angle spinning and in uniformly 13C-labeled systems, Journal of Chemical Physics, 118, 8378, 10.1063/1.1565109 Cheeseman, 1996, A comparison of models for calculating nuclear magnetic resonance shielding tensors, The Journal of Chemical Physics, 104, 5497, 10.1063/1.471789 Choudhury, 2012, Chain dynamics in antiplasticized and annealed poly(ethylene terephthalate) determined by solid-state NMR and correlated with enhanced barrier properties, Macromolecules, 45, 879, 10.1021/ma202012h de Ilarduya, 2014, Chemical structure and microstructure of poly(alkylene terephthalate)s, their copolyesters, and their blends as studied by NMR, Macromolecular Chemistry and Physics, 215, 2138, 10.1002/macp.201400239 deAzevedo, 1999, Centerband-only detection of exchange: Efficient analysis of dynamics in solids by NMR, Journal of the American Chemical Society, 121, 8411, 10.1021/ja992022v deAzevedo, 2008, Intermediate motions as studied by solid-state separated local field NMR experiments, The Journal of Chemical Physics, 128, 104505, 10.1063/1.2831798 Donovan, 2005, A novel method for determination of polyester end-groups by NMR spectroscopy, Polymer, 46, 5005, 10.1016/j.polymer.2005.04.032 2002 Dunning, 1989, Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen, The Journal of Chemical Physics, 90, 1007, 10.1063/1.456153 Falkenstein, 2020, UV pretreatment impairs the enzymatic degradation of polyethylene terephthalate, Frontiers in Microbiology, 11, 689, 10.3389/fmicb.2020.00689 Fox, 1997, Characterization of poly(ethylene terephthalate) and poly(ethylene terephthalate) blends, Polymer, 38, 3035, 10.1016/S0032-3861(96)00872-5 Gabriëlse, 1994, 13C solid-state NMR study of differently processed poly(ethylene terephthalate) yarns, Macromolecules, 27, 5811, 10.1021/ma00098a040 Grimme, 2010, A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu, The Journal of Chemical Physics, 132, 154104, 10.1063/1.3382344 Grimme, 2011, Effect of the damping function in dispersion corrected density functional theory, Journal of Computational Chemistry, 32, 1456, 10.1002/jcc.21759 Guan, 2010, A general protocol for temperature calibration of MAS NMR probes at arbitrary spinning speeds, Solid State Nuclear Magnetic Resonance, 38, 74, 10.1016/j.ssnmr.2010.10.001 Günther, 2013 2018 Hong, 1997, Site-resolved determination of peptide torsion angle ϕ from the relative orientations of backbone N–H and C–H bonds by solid-state NMR, The Journal of Physical Chemistry B, 101, 5869, 10.1021/jp970887u Huster, 2001, Solid-state NMR investigation of the dynamics of the soluble and membrane-bound colicin Ia channel-forming domain, Biochemistry, 40, 7662, 10.1021/bi0027231 Hutchinson, 1995, Physical aging of polymers, Progress in Polymer Science, 20, 703, 10.1016/0079-6700(94)00001-I Ivanir-Dabora, 2015, Site-resolved backbone and side-chain intermediate dynamics in a carbohydrate-binding module protein studied by magic-angle spinning NMR spectroscopy, Chemistry—A European Journal, 21, 10778, 10.1002/chem.201500856 Jeener, 1979, Investigation of exchange processes by two-dimensional NMR spectroscopy, The Journal of Chemical Physics, 71, 4546, 10.1063/1.438208 Jensen, 2015, Segmented contracted basis sets optimized for nuclear magnetic shielding, Journal of Chemical Theory and Computation, 11, 132, 10.1021/ct5009526 Joo, 2018, Structural insight into molecular mechanism of poly(ethylene terephthalate) degradation, Nature Communications, 9, 382, 10.1038/s41467-018-02881-1 Kenwright, 1999, End group modification in poly(ethylene terephthalate), Polymer, 40, 2035, 10.1016/S0032-3861(98)00433-9 Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review B, 37, 785, 10.1103/PhysRevB.37.785 Liu, 2002, A robust technique for two-dimensional separation of undistorted chemical-shift anisotropy powder patterns in magic-angle-spinning NMR, Journal of Magnetic Resonance, 155, 15, 10.1006/jmre.2002.2503 Ma, 2003, NMR based determination of minute acid functionality: End-groups in PET, Polymer, 44, 4429, 10.1016/S0032-3861(03)00402-6 Metz, 1994, Ramped-amplitude cross polarization in magic-angle-spinning NMR, Journal of Magnetic Resonance, Series A, 110, 219, 10.1006/jmra.1994.1208 Paul, 2009, Supercycled homonuclear dipolar decoupling sequences in solid-state NMR, Journal of Magnetic Resonance, 197, 14, 10.1016/j.jmr.2008.11.011 Peez, 2019, The first application of quantitative 1H NMR spectroscopy as a simple and fast method of identification and quantification of microplastic particles (PE, PET, and PS), Analytical and Bioanalytical Chemistry, 411, 823, 10.1007/s00216-018-1510-z Perrin, 1990, Application of two-dimensional NMR to kinetics of chemical exchange, Chemical Reviews, 90, 935, 10.1021/cr00104a002 Pritchard, 2019, New basis set exchange: An open, up-to-date resource for the molecular sciences community, Journal of Chemical Information and Modeling, 59, 4814, 10.1021/acs.jcim.9b00725 Qian, 1996, The effects of physical ageing on conformational changes of poly(ethylene terephthalate) in the glass transition region, Macromolecular Chemistry and Physics, 197, 1485, 10.1002/macp.1996.021970425 Reichert, 2001, Slow-down of 13C spin diffusion in organic solids by fast MAS: A CODEX NMR study, Journal of Magnetic Resonance, 151, 129, 10.1006/jmre.2001.2337 Roberts, 1984, Two-dimensional heteronuclear chemical shift correlation spectroscopy in rotating solids, Journal of the American Chemical Society, 106, 2506, 10.1021/ja00321a003 Ronkvist, 2009, Cutinase-catalyzed hydrolysis of poly(ethylene terephthalate), Macromolecules, 42, 5128, 10.1021/ma9005318 Roth, 2014, Structural and functional studies on a thermostable polyethylene terephthalate degrading hydrolase from Thermobifida fusca, Applied Microbiology and Biotechnology, 98, 7815, 10.1007/s00253-014-5672-0 Schaefer, 1976, Carbon-13 nuclear magnetic resonance of polymers spinning at the magic angle, Journal of the American Chemical Society, 98, 1031, 10.1021/ja00420a036 Schaefer, 1980, Carbon-13 T1ρ experiments on solid glassy polymers, Macromolecules, 13, 1121, 10.1021/ma60077a018 Schmidt-Rohr, 1998, Elucidation of the chain conformation in a glassy polyester, PET, by two-dimensional NMR, Science, 280, 714, 10.1126/science.280.5364.714 Schmidt-Rohr, 1994 Sefcik, 1980, Analysis of the room-temperature molecular motions of poly(ethylene terephthalate), Macromolecules, 13, 1132, 10.1021/ma60077a020 Steffen, 2010, TmoleX—A graphical user interface for TURBOMOLE, Journal of Computational Chemistry, 31, 2967, 10.1002/jcc.21576 Sulaiman, 2012, Isolation of a novel cutinase homolog with polyethylene terephthalate-degrading activity from leaf-branch compost by using a metagenomic approach, Applied and Environmental Microbiology, 78, 1556, 10.1128/AEM.06725-11 Thakur, 2006, Swept-frequency two-pulse phase modulation for heteronuclear dipolar decoupling in solid-state NMR, Chemical Physics Letters, 426, 459, 10.1016/j.cplett.2006.06.007 Tournier, 2020, An engineered PET depolymerase to break down and recycle plastic bottles, Nature, 580, 216, 10.1038/s41586-020-2149-4 VanderHart, 1979, 13C NMR rotating frame relaxation in a solid with strongly coupled protons: Polyethylene, The Journal of Chemical Physics, 71, 2773, 10.1063/1.438682 Vertommen, 2005, Enzymatic surface modification of poly(ethylene terephthalate), Journal of Biotechnology, 120, 376, 10.1016/j.jbiotec.2005.06.015 Vinod Chandran, 2008, Swept-frequency two-pulse phase modulation (SWf-TPPM) sequences with linear sweep profile for heteronuclear decoupling in solid-state NMR, Magnetic Resonance in Chemistry, 46, 943, 10.1002/mrc.2285 Vinogradov, 2001, Phase modulated Lee-Goldburg magic angle spinning proton nuclear magnetic resonance experiments in the solid state: A bimodal Floquet theoretical treatment, Journal of Chemical Physics, 115, 8983, 10.1063/1.1408287 Wang, 2018, Spin-echo based diagonal peak suppression in solid-state MAS NMR homonuclear chemical shift correlation spectra, Journal of Magnetic Resonance, 287, 91, 10.1016/j.jmr.2017.12.019 Wei, 2019, Biocatalytic degradation efficiency of postconsumer polyethylene terephthalate packaging determined by their polymer microstructures, Advanced Science, 6, 1900491, 10.1002/advs.201900491 Wei, 2019, Conformational fitting of a flexible oligomeric substrate does not explain the enzymatic PET degradation, Nature Communications, 10, 5581, 10.1038/s41467-019-13492-9 Wei, 2017, Biocatalysis as a green route for recycling the recalcitrant plastic polyethylene terephthalate, Microbial Biotechnology, 10, 1302, 10.1111/1751-7915.12714 Wilhelm, 1996, Detection of slow 180° phenylene flips in PET fibers via 13C two-dimensional solid-state exchange NMR, Macromolecules, 29, 1088, 10.1021/ma9516192 Zemke, 1991, Conformational exchange near the glass transition: Two-dimensional 13C NMR study of atactic polypropylene, Macromolecules, 24, 6874, 10.1021/ma00026a017