Cooperative polymerization of α-helices induced by macromolecular architecture

Nature Chemistry

Volumn 9, Issue 7, 2017, Pages 614-622

  Baumgartner, Ryan ^a   Fu, Hailin ^b   Song, Ziyuan ^c   Lin, Yao ^b   Cheng, Jianjun ^a,c  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

^c University of Illinois at Urbana Champaign   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE; PROTEIN;

ALPHA HELIX; CATALYSIS; CHEMISTRY; MACROMOLECULE; POLYMERIZATION; SYNTHESIS;

CATALYSIS; MACROMOLECULAR SUBSTANCES; PEPTIDES; POLYMERIZATION; PROTEIN CONFORMATION, ALPHA-HELICAL; PROTEINS;

EID: 85021266409     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2712     Document Type: Article

References (44)

1. Breslow, R. Biomimetic chemistry and artificial enzymes: catalysis by design. Acc. Chem. Res. 28, 146-153 (1995).
2. Dong, Z., Luo, Q. & Liu, J. Artificial enzymes based on supramolecular scaffolds. Chem. Soc. Rev. 41, 7890-7908 (2012).
3. Kuah, E., Toh, S., Yee, J., Ma, Q. & Gao, Z. Enzyme mimics: advances and applications. Chem. Eur. J. 22, 8404-8430 (2016).
4. Lund, K. et al. Molecular robots guided by prescriptive landscapes. Nature 465, 206-210 (2010).
5. Wickham, S. F. J. et al. A DNA-based molecular motor that can navigate a network of tracks. Nat. Nanotechnol. 7, 169-173 (2012).
6. Erbas-Cakmak, S., Leigh, D. A., McTernan, C. T. & Nussbaumer, A. L. Artificial molecular machines. Chem. Rev. 115, 10081-10206 (2015).
7. Browne, W. R. & Feringa, B. L. Making molecular machines work. Nat. Nanotechnol. 1, 25-35 (2006).
8. van Dongen, S. F. M., Cantekin, S., Elemans, J. A. A. W., Rowan, A. E. & Nolte, R. J. M. Functional interlocked systems. Chem. Soc. Rev. 43, 99-122 (2014).
9. Epstein, I. R. & Xu, B. Reaction-diffusion processes at the nano- and microscales. Nat. Nanotechnol. 11, 312-319 (2016).
10. Boekhoven, J., Hendriksen, W. E., Koper, G. J. M., Eelkema, R. & van Esch, J. H. Transient assembly of active materials fueled by a chemical reaction. Science 349, 1075-1079 (2015).
11. Sadownik, J. W., Mattia, E., Nowak, P. & Otto, S. Diversification of selfreplicating molecules. Nat. Chem. 8, 264-269 (2016).
12. Lewandowski, B. et al. Sequence-specific peptide synthesis by an artificial smallmolecule machine. Science 339, 189-193 (2013).
13. Korevaar, P. A. et al. Pathway complexity in supramolecular polymerization. Nature 481, 492-496 (2012).
14. Aliprandi, A., Mauro, M. & De Cola, L. Controlling and imaging biomimetic self-assembly. Nat. Chem. 8, 10-15 (2016).
15. Korevaar, P. A., Newcomb, C. J., Meijer, E.W. & Stupp, S. I. Pathway selection in peptide amphiphile assembly. J. Am. Chem. Soc. 136, 8540-8543 (2014).
16. Yu, Z. et al. Simultaneous covalent and noncovalent hybrid polymerizations. Science 351, 497-502 (2016).
17. Zhao, D. & Moore, J. S. Nucleation-elongation: a mechanism for cooperative supramolecular polymerization. Org. Biomol. Chem. 1, 3471-3491 (2003).
18. Oosawa, F. & Asakura, S. Thermodynamics of the Polymerization of Protein (Academic Press, 1975).
19. Luders, J. & Stearns, T. Microtubule-organizing centres: a re-evaluation. Nat. Rev. Mol. Cell Biol. 8, 161-167 (2007).
20. Dominguez, R. & Holmes, K. C. Actin structure and function. Annu. Rev. Biophys. 40, 169-186 (2011).
21. De Greef, T. F. A. et al. Supramolecular polymerization. Chem. Rev. 109, 5687-5754 (2009).
22. McHale, R., Patterson, J. P., Zetterlund, P. B. & O'Reilly, R. K. Biomimetic radical polymerization via cooperative assembly of segregating templates. Nat. Chem. 4, 491-497 (2012).
23. Lu, H., Wang, J., Lin, Y. & Cheng, J. One-pot synthesis of brush-like polymers via integrated ring-opening metathesis polymerization and polymerization of amino acid N-carboxyanhydrides. J. Am. Chem. Soc. 131, 13582-13583 (2009).
24. Lu, H. & Cheng, J. N-Trimethylsilyl amines for controlled ring-opening polymerization of amino acid N-carboxyanhydrides and facile end froup functionalization of polypeptides. J. Am. Chem. Soc. 130, 12562-12563 (2008).
25. Goodman, M., Verdini, A. S., Toniolo, C., Phillips, W. D. & Bovey, F. A. Sensitive criteria for the critical size for helix formation in oligopeptides. Proc. Natl Acad. Sci. USA 64, 444-450 (1969).
26. Rinaudo, M. & Domard, A. Circular dichroism studies on α-L-glutamic acid oligomers in solution. J. Am. Chem. Soc. 98, 6360-6364 (1976).
27. Mutter, M. The influence of the macromolecular protecting group in conformational studies on polyoxyethylene-bound peptides. Macromolecules 10, 1413-1414 (1977).
28. Ballard, D. G. H. & Bamford, C. H. The heterogeneous polymerization of α-N-carboxyamino-acid anhydrides. J. Chem. Soc. 1039-1044 (1959).
29. Kōmoto, T., Akaishi, T., Ōya, M. & Kawai, T. Crystallization of polypeptides in the course of polymerization. I.: Growth mechanism of poly-L- and DL-alanine crystals. Makromol. Chem. 154, 151-159 (1972).
30. Hadjichristidis, N., Iatrou, H., Pitsikalis, M. & Sakellariou, G. Synthesis of welldefined polypeptide-based materials via the ring-opening polymerization of α-amino acid N-carboxyanhydrides. Chem. Rev. 109, 5528-5578 (2009).
31. Deming, T. J. Polypeptide and Polypeptide Hybrid Copolymer Synthesis via NCA Polymerization (Springer, 2006).
32. Blout, E. R. & Idelson, M. Polypeptides IX. the kinetics of strong-base initiated polymerizations of amino acid-N-carboxyanhydrides. J. Am. Chem. Soc. 78, 3857-3858 (1956).
33. Lu, H. & Cheng, J. Hexamethyldisilazane-mediated controlled polymerization of α-amino acid N-carboxyanhydrides. J. Am. Chem. Soc. 129, 14114-14115 (2007).
34. Lundberg, R. D. & Doty, P. Polypeptides XVII. a study of the kinetics of the primary amine-initiated polymerization of N-carboxy-anhydrides with special reference to configurational and stereochemical effects. J. Am. Chem. Soc. 79, 3961-3972 (1957).
35. Blout, E. R. & Asadourian, A. Polypeptides. V. the infrared spectra of polypeptides derived from γ-benzyl-L-glutamate. J. Am. Chem. Soc. 78, 955-961 (1956).
36. Ling, J. & Huang, Y. Understanding the ring-opening reaction of α-amino acid N-carboxyanhydride in an amine-mediated living polymerization: a DFT study. Macromol. Chem. Phys. 211, 1708-1711 (2010).
37. Kricheldorf, H. R. α-Aminoacid-N-Carboxy-Anhydrides and Related Heterocycles (Springer, 1987).
38. Weingarten, H. Kinetics and mechanisms of the polymerization of N-carboxy-α- amino acid anhydrides. J. Am. Chem. Soc. 80, 352-355 (1958).
39. Kelly, D. R. & Roberts, S. M. The mechanism of polyleucine catalysed asymmetric epoxidation. Chem. Commun. 2018-2020 (2004).
40. Mathew, S. P., Gunathilagan, S., Roberts, S. M. & Blackmond, D. G. Mechanistic insights from reaction progress kinetic analysis of the polypeptide-catalyzed epoxidation of chalcone. Org. Lett. 7, 4847-4850 (2005).
41. Aragonès, A. C. et al. Electrostatic catalysis of a Diels-Alder reaction. Nature 531, 88-91 (2016).
42. Yu, M., Nowak, A. P., Deming, T. J. & Pochan, D. J. Methylated mono- and diethyleneglycol functionalized polylysines: nonionic, α-helical, water-soluble polypeptides. J. Am. Chem. Soc. 121, 12210-12211 (1999).
43. Rzayev, J. Synthesis of polystyrene-polylactide bottlebrush block copolymers and their melt self-assembly into large domain nanostructures. Macromolecules 42, 2135-2141 (2009).
44. Neugebauer, D., Sumerlin, B. S., Matyjaszewski, K., Goodhart, B. & Sheiko, S. S. How dense are cylindrical brushes grafted from a multifunctional macroinitiator? Polymer 45, 8173-8179 (2004).