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Alternating Copolymers Based on Amino Acids and Peptides

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Advances in Sustainable Polymers

Abstract

Controlling the monomer sequence along the polymer chain leads to the development of a special class of synthetic copolymers, and they are known as alternating copolymers when the two comonomers are placed in a regular exchanging fashion. The monomer sequence control plays an important role to regulate the different bulk properties such as conductivity, rigidity, biodegradability, as well as mimic the properties of the sequence defined biopolymers like DNA, RNA, enzymes, and proteins. Very recently, different synthetic strategies have been explored to mimic the monomer sequences in synthetic polymeric materials. An enormous combination of several desired functionalities has been attached with the electron donor styrene, stilbene or electron acceptor maleic anhydride or N-substituted maleimide moieties to produce strictly alternating backbone and their properties have been extensively investigated. Nowadays, functionalities like amino acids and peptides, essential and fundamental components of protein biopolymers and alive entities extending from bacteria to humans with a variety of enormities from nano to macro dimension, are widely used to design an extensive range of block or random copolymers with significant assets and applications, as they can play critical responsibility in both functional and structural levels. The multifaceted biological features of these moieties help to generate bioactive and biocompatible materials. However, the properties associated with their alternating architecture have not been broadly studied. By providing a quick look on different types of alternating copolymers, in this book chapter, we aim to focus on recent developments of amino acid and peptide-based alternating architectures, their interesting properties and applications as bioinspired nanomaterials, in inclusion chemistry, catalysis, sensing, tissue engineering, molecular electronics, molecular separation technology, and so on.

Authors Ishita Mukherjee and Krishna Gopal Goswami are contributed equally to this work.

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References

  1. Matyjaszewski K (2005) Macromolecular engineering: from rational design through precise macromolecular synthesis and processing to targeted macroscopic material properties. Prog Polym Sci 30:858–875. https://doi.org/10.1016/j.progpolymsci.2005.06.004

    Article  CAS  Google Scholar 

  2. (a) Pyun J, Zhou XZ, Drockenmuller E, Hawker CJ (2003) Macromolecules of controlled architecture. J Mat Chem 13:2653–2660. https://doi.org/10.1039/b304682f; (b) Bernaerts KV, Du Prez FE (2006) Dual/heterofunctional initiators for the combination of mechanistically distinct polymerization techniques. Prog Polym Sci 31:671–722. https://doi.org/10.1016/j.progpolymsci.2006.08.007; (c) Lutz J-F (2007) 1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. Angew Chem Int Ed 46:1018–1025. https://doi.org/10.1002/anie.200604050; (d) McCormick CL, Sumerlin BS, Lokitz BS, Stempka JE (2008) RAFT-synthesized diblock and triblock copolymers: thermally-induced supramolecular assembly in aqueous media. Soft Matter 4:1760–1773. https://doi.org/10.1039/b719577j; (e) Moad G, Rizzardo E, Thang SH (2008) Radical addition–fragmentation chemistry in polymer synthesis. Polymer 49:1079–1131. https://doi.org/10.1016/j.polymer.2007.11.020

  3. Yokota K (1999) Periodic copolymers. Prog Polym Sci 24:517–563. https://doi.org/10.1016/S0079-6700(99)00010-6

    Article  CAS  Google Scholar 

  4. Matyjaszewski K, Ziegler MJ, Arehart SV, Greszta D, Pakula T (2000) Gradient copolymers by atom transfer radical copolymerization. J Phys Org Chem 13:775–786. https://doi.org/10.1002/1099-1395(200012)13:12%3c775:AID-POC314%3e3.0.CO;2-D

    Article  CAS  Google Scholar 

  5. Lutz J-F (2014) Aperiodic copolymers. ACS Macro Lett 3:1020–1023. https://doi.org/10.1021/mz5004823

    Article  CAS  Google Scholar 

  6. Badi N, Chan-Seng D, Lutz J-F (2013) Microstructure control: an underestimated parameter in recent polymer design. Macromol Chem Phys 214:135–142. https://doi.org/10.1002/macp.201200475

    Article  CAS  Google Scholar 

  7. Lutz J-F (2010) A controlled sequence of events. Nat Chem 2:84–85. https://doi.org/10.1038/nchem.530

    Article  CAS  Google Scholar 

  8. Badi N, Lutz J-F (2009) Sequence control in polymer synthesis. Chem Soc Rev 38:3383–3390. https://doi.org/10.1039/B806413J

    Article  CAS  Google Scholar 

  9. Ouchi M, Badi N, Lutz J-F, Sawamoto M (2011) Single-chain technology using discrete synthetic macromolecules. Nat Chem 3:917–924. https://doi.org/10.1038/nchem.1175

    Article  CAS  Google Scholar 

  10. Lutz J-F (2010) Sequence-controlled polymerizations: the next Holy Grail in polymer science? Polym Chem 1:55–62. https://doi.org/10.1039/B9PY00329K

    Article  CAS  Google Scholar 

  11. Schmidt BVKJ, Fechler N, Falkenhagen J, Lutz J-F (2011) Controlled folding of synthetic polymer chains through the formation of positionable covalent bridges. Nat Chem 3:234–238. https://doi.org/10.1038/nchem.964

    Article  CAS  Google Scholar 

  12. Lutz J-F, Ouchi M, Liu DR, Sawamoto M (2013) Sequence-controlled polymers. Science 341:628–636. https://doi.org/10.1126/science.1238149

  13. Espeel P, Carrette LLG, Bury K, Capenberghs S, Martins JC, Du Prez FE, Madder A (2013) Multifunctionalized sequence-defined oligomers from a single building block. Angew Chem Int Ed 52:13261–13264. https://doi.org/10.1002/anie.201307439

    Article  CAS  Google Scholar 

  14. Solleder SC, Meier MAR (2014) Sequence control in polymer chemistry through the Passerini three-component reaction. Angew Chem Int Ed 53:711–714. https://doi.org/10.1002/anie.201308960

    Article  CAS  Google Scholar 

  15. Satoh K, Ozawa S, Mizutani M, Nagai K, Kamigaito M (2010) Sequence-regulated vinyl copolymers by metal-catalysed step-growth radical polymerization. Nat Commun 1:1–6. https://doi.org/10.1038/ncomms1004

    Article  CAS  Google Scholar 

  16. Niu J, Hili R, Liu DR (2013) Enzyme-free translation of DNA into sequence-defined synthetic polymers structurally unrelated to nucleic acids. Nat Chem 5:282–292. https://doi.org/10.1038/nchem.1577

    Article  CAS  Google Scholar 

  17. Zhang Q, Collins J, Anastasaki A, Wallis R, Mitchell DA, Becer CR, Haddleton DM (2013) Sequence-controlled multi-block glycopolymers to inhibit DC-SIGN-gp120 binding. Angew Chem 125:4531–4535. https://doi.org/10.1002/ange.201300068

    Article  Google Scholar 

  18. Gody G, Maschmeyer T, Zetterlund PB, Perrier S (2013) Rapid and quantitative one-pot synthesis of sequence-controlled polymers by radical polymerization. Nat Commun 4:2505 (1–9). https://doi.org/10.1038/ncomms3505

  19. Pfeifer S, Lutz J-F (2007) A facile procedure for controlling monomer sequence distribution in radical chain polymerizations. J Am Chem Soc 129:9542–9543. https://doi.org/10.1021/ja0717616

  20. Satoh K, Matsuda M, Nagai K, Kamigaito M (2010) A AB-sequence living radical chain copolymerization of naturally occurring limonene with maleimide: an end-to-end sequence-regulated copolymer. J Am Chem Soc 132:10003–10005. https://doi.org/10.1021/ja1042353

    Article  CAS  Google Scholar 

  21. IUPAC (1997) Compendium of chemical terminology (the “Gold Book”), 2nd edn. Blackwell Scientific Publications, Oxford

    Google Scholar 

  22. Odian G (2004) Principles of polymerization. Wiley, Hoboken, NJ

    Book  Google Scholar 

  23. Huang J, Turner SR (2017) Recent advances in alternating copolymers: the synthesis, modification, and applications of precision polymers. Polymer 116:572–586. https://doi.org/10.1016/j.polymer.2017.01.020

    Article  CAS  Google Scholar 

  24. Berthet M-A, Zarafshani Z, Pfeifer S, Lutz J-F (2010) Facile synthesis of functional periodic copolymers: a step toward polymer-based molecular arrays. Macromolecules 43:44–50. https://doi.org/10.1021/ma902075q

    Article  CAS  Google Scholar 

  25. Ramakers BEI, van Hest JCM, Lowik DWPM (2014) Molecular tools for the construction of peptide-based materials. Chem Soc Rev 43:2743–2756. https://doi.org/10.1039/C3CS60362H

    Article  CAS  Google Scholar 

  26. Deng C, Wu J, Cheng R, Meng F, Klok H-A, Zhong Z (2014) Functional polypeptide and hybrid materials: precision synthesis via α-amino acid N-carboxyanhydride polymerization and emerging biomedical applications. Prog Polym Sci 39:330–364. https://doi.org/10.1016/j.progpolymsci.2013.10.008

    Article  CAS  Google Scholar 

  27. Secker C, Brosnan SM, Luxenhofer R, Schlaad H (2015) Poly(α-peptoid)s revisited: synthesis, properties, and use as biomaterial. Macromol Biosci 15:881–891. https://doi.org/10.1002/mabi.201500023

    Article  CAS  Google Scholar 

  28. Sedman VL, Chen X, Allen S, Roberts CJ, Korolkov VV, Tendler SJB (2013) Tuning the mechanical properties of self-assembled mixed-peptide tubes. J Microsc 249:165–172. https://doi.org/10.1111/jmi.12005

    Article  CAS  Google Scholar 

  29. Orbach R, Mironi-Harpaz I, Adler-Abramovich L, Mossou E, Mitchell EP, Forsyth VT, Gazit E, Seliktar D (2012) The rheological and structural properties of fmoc-peptide-based hydrogels: the effect of aromatic molecular architecture on self-assembly and physical characteristics. Langmuir 28:2015–2022. https://doi.org/10.1021/la204426q

    Article  CAS  Google Scholar 

  30. Bauri K, Pant S, Roy SG, De P (2013) Dual pH and temperature responsive helical copolymer libraries with pendant chiral leucine moieties. Polym Chem 4:4052–4060. https://doi.org/10.1039/C3PY00434A

    Article  CAS  Google Scholar 

  31. Kumar S, Acharya R, Chatterji U, De P (2013) Side-chain amino-acid-based ph-responsive self-assembled block copolymers for drug delivery and gene transfer. Langmuir 29:15375–15385. https://doi.org/10.1021/la403819g

    Article  CAS  Google Scholar 

  32. Alfrey T, Lavin E (1945) The copolymerization of styrene and maleic anhydride. J Am Chem Soc 67:2044–2045. https://doi.org/10.1021/ja01227a502

    Article  CAS  Google Scholar 

  33. Oishi A, Matsuoka H, Yasuda T, Watanabe M (2009) Novel styrene/N-phenylmaleimide alternating copolymers with pendant sulfonimide acid groups for polymer electrolyte fuel cell applications. J Mater Chem 19:514–521. https://doi.org/10.1039/B815390F

    Article  CAS  Google Scholar 

  34. Mohamed MG, Hsu K-C, Hong J-L, Kuo S-W (2016) Unexpected fluorescence from maleimide-containing polyhedral oligomeric silsesquioxanes: nanoparticle and sequence distribution analyses of polystyrene-based alternating copolymers. Polym Chem 7:135–145. https://doi.org/10.1039/C5PY01537E

    Article  CAS  Google Scholar 

  35. Qiu G-M, Zhu B-K, Xu Y-Y, Geckeler KE (2006) Synthesis of ultrahigh molecular weight poly(styrene-alt-maleic anhydride) in supercritical carbon dioxide. Macromolecules 39:3231–3237. https://doi.org/10.1021/ma052520q

    Article  CAS  Google Scholar 

  36. Wu D-C, Hong C-Y, Pan C-Y, He W-D (2003) Study on controlled radical alternating copolymerization of styrene with maleic anhydride under UV irradiation. Polym Int 52:98–103. https://doi.org/10.1002/pi.1039

    Article  CAS  Google Scholar 

  37. Montaudo MS (2001) Determination of the compositional distribution and compositional drift in styrene/maleic anhydride copolymers. Macromolecules 34:2792–2797. https://doi.org/10.1021/ma0010231

    Article  CAS  Google Scholar 

  38. Klumperman B (2010) Mechanistic considerations on styrene–maleic anhydride copolymerization reactions. Polym Chem 1:558–562. https://doi.org/10.1039/B9PY00341J

    Article  CAS  Google Scholar 

  39. Benoit D, Hawker CJ, Huang EE, Lin Z, Russell TP (2000) One-step formation of functionalized block copolymers. Macromolecules 33:1505–1507. https://doi.org/10.1021/ma991721p

    Article  CAS  Google Scholar 

  40. Wang Y, Shen Y, Pei X, Zhang S, Liu H, Ren J (2008) In situ synthesis of poly(styrene-co-maleic anhydride)/SiO2 hybrid composites via “grafting onto” strategy based on nitroxide-mediated radical polymerization. React Funct Polym 68:1225–1230. https://doi.org/10.1016/j.reactfunctpolym.2008.05.003

    Article  CAS  Google Scholar 

  41. Williams EGL, Fairbanks B, Moad G, Mulder RJ, Rizzardo E, Thang SH (2015) Preparation of 1:1 alternating, nucleobase-containing copolymers for use in sequence-controlled polymerization. Polym Chem 6:228–232. https://doi.org/10.1039/C4PY01247J

    Article  CAS  Google Scholar 

  42. Wang S, Wu B, Liu F, Gao Y, Zhang W (2015) A well-defined alternating copolymer based on a salicylaldimine Schiff base for highly sensitive zinc(II) detection and pH sensing in aqueous solution. Polym Chem 6:1127–1136. https://doi.org/10.1039/C4PY01298D

    Article  CAS  Google Scholar 

  43. Saha B, Bauri K, Bag A, Ghorai PK, De P (2016) Conventional fluorophore-free dual pH- and thermo-responsive luminescent alternating copolymer. Polym Chem 7:6895–6900. https://doi.org/10.1039/C6PY01738J

    Article  CAS  Google Scholar 

  44. Wenyan H, Huili P, Bibiao J, Qiang R, Guangqun Z, Lizhi K, Dongliang Z, Jianhai C (2011) Preparation of heat-resistant branched poly(styrene-alt-NPMI) by ATRP with divinylbenzene as the branching agent. J Appl Polym Sci 119:977–982. https://doi.org/10.1002/app.32814

    Article  CAS  Google Scholar 

  45. Chen GQ, Wu ZQ, Wu JR, Li ZC, Li FM (2000) Synthesis of alternating copolymers of n-substituted maleimides with styrene via atom transfer radical polymerization. Macromolecules 33:232–234. https://doi.org/10.1021/ma991047b

    Article  CAS  Google Scholar 

  46. Lutz J-F, Schmidt BVKJ, Pfeifer S (2011) Tailored polymer microstructures prepared by atom transfer radical copolymerization of styrene and n-substituted maleimides. Macromol Rapid Commun 32:127–135. https://doi.org/10.1002/marc.201000664

    Article  CAS  Google Scholar 

  47. Sanders GC, Duchateau R, Lin CY, Coote ML, Heuts JPA (2012) End-functional styrene–maleic anhydride copolymers via catalytic chain transfer polymerization. Macromolecules 45:5923–5933. https://doi.org/10.1021/ma301161u

    Article  CAS  Google Scholar 

  48. Longo JM, DiCiccio AM, Coates GW (2014) Poly(propylene succinate): a new polymer stereocomplex. J Am Chem Soc 136:15897–15900. https://doi.org/10.1021/ja509440g

    Article  CAS  Google Scholar 

  49. Kramer JW, Treitler DS, Dunn EW, Castro PM, Roisnel T, Thomas CM, Coates GW (2009) Polymerization of enantiopure monomers using syndiospecific catalysts: a new approach to sequence control in polymer synthesis. J Am Chem Soc 131:16042–16044. https://doi.org/10.1021/ja9075327

    Article  CAS  Google Scholar 

  50. Li J, He J (2015) Synthesis of sequence-regulated polymers: alternating polyacetylene through regioselective anionic polymerization of butadiene derivatives. ACS Macro Lett 4:372–376. https://doi.org/10.1021/acsmacrolett.5b00125

    Article  CAS  Google Scholar 

  51. Stayshich RM, Meyer TY (2008) Preparation and microstructural analysis of poly(lactic-alt-glycolic acid). J Polym Sci Part A Polym Chem 46:4704–4711. https://doi.org/10.1002/pola.22801

    Article  CAS  Google Scholar 

  52. Tsuji H, Arakawa Y (2018) Synthesis, properties, and crystallization of the alternating stereocopolymer poly(L-lactic acid-alt-D-lactic acid) [syndiotactic poly(lactic acid)] and its blend with isotactic poly(lactic acid). Polym Chem 9:2446–2457. https://doi.org/10.1039/C8PY00391B

    Article  CAS  Google Scholar 

  53. Mayo FR, Lewis FM (1944) Copolymerization. I. A basis for comparing the behavior of monomers in copolymerization; the copolymerization of styrene and methyl methacrylate. J Am Chem Soc 66:1594–1601. https://doi.org/10.1021/ja01237a052

    Article  CAS  Google Scholar 

  54. Fukuda T, Ma Y-D, Kubo K, Inagaki H (1991) Penultimate-unit effects in free-radical copolymerization. Macromolecules 24:370–375. https://doi.org/10.1021/ma00002a005

    Article  CAS  Google Scholar 

  55. Sanayei RA, O’Driscoll KF, Klumperman B (1994) Pulsed laser copolymerization of styrene and maleic anhydride. Macromolecules 27:5577–5582. https://doi.org/10.1021/ma00098a010

    Article  CAS  Google Scholar 

  56. Fukuda T, Kubo K, Ma Y-D (1992) Kinetics of free radical copolymerization. Prog Polym Sci 17:875–916. https://doi.org/10.1016/0079-6700(92)90012-N

    Article  CAS  Google Scholar 

  57. Jones SA, Prementine GS, Tirrell DA (1985) Model copolymerization reactions. Direct observation of a “penultimate effect” in a model styrene-acrylonitrile copolymerization. J Am Chem Soc 107:5275–5276. https://doi.org/10.1021/ja00304a042

    Article  CAS  Google Scholar 

  58. Tsuchida E, Tomono T (1971) Discussion on the mechanism of alternating copolymerization of styrene and maleic anhydride. Makromol Chem 141:265–298. https://doi.org/10.1002/macp.1971.021410122

    Article  CAS  Google Scholar 

  59. Zhao Y, Li H, Liu P, Liu H, Jiang J, Xi F (2002) Reactivity ratios of free monomers and their charge-transfer complex in the copolymerization of N-butyl maleimide and styrene. J Appl Polym Sci 83:3007–3012. https://doi.org/10.1002/app.2330

    Article  CAS  Google Scholar 

  60. Dodgson K, Ebdon JR (1977) On the role of monomer—monomer donor—acceptor complexes in the free-radical copolymerisation of styrene and maleic anhydride. Eur Polym J 13:791–797. https://doi.org/10.1016/0014-3057(77)90024-6

    Article  CAS  Google Scholar 

  61. Deb PC, Meyerhoff G (1985) Study on kinetics of copolymerization of styrene and maleic anhydride in methyl ethyl ketone. Polymer 26:629–635. https://doi.org/10.1016/0032-3861(85)90166-1

    Article  CAS  Google Scholar 

  62. Hall HK, Padias AB (2001) “Charge transfer” polymerization—and the absence thereof! J Polym Sci Part A Polym Chem 39:2069–2077. https://doi.org/10.1002/pola.1183

    Article  CAS  Google Scholar 

  63. Haldar U, Pan A, Mukherjee I, De P (2016) POSS semitelechelic Aβ17–19 peptide initiated helical polypeptides and their structural diversity in aqueous medium. Polym Chem 7:6231–6240. https://doi.org/10.1039/C6PY01399F

    Article  CAS  Google Scholar 

  64. Heitz F, Spach G (1971) Synthesis and conformational study of alternating poly(γ-benzyl D,L-glutamates). Macromolecules 4:429–432. https://doi.org/10.1021/ma60022a011

    Article  Google Scholar 

  65. Seipke G, Arfmann H-A, Wagner KG (1974) Synthesis and properties of alternating poly(Lys-Phe) and comparison with the random copolymer poly(Lys51, Phe49). Biopolymers 13:1621–1633. https://doi.org/10.1002/bip.1974.360130809

    Article  CAS  Google Scholar 

  66. Li G, Raman VK, Xie W, Gross RA (2008) Protease-catalyzed co-oligomerizations of L-leucine ethyl ester with L-glutamic acid diethyl ester: sequence and chain length distributions. Macromolecules 41:7003–7012. https://doi.org/10.1021/ma800946d

    Article  CAS  Google Scholar 

  67. DiMarco RL, Heilshorn SC (2012) Multifunctional materials through modular protein engineering. Adv Mater 24:3923–3940. https://doi.org/10.1002/adma.201200051

    Article  CAS  Google Scholar 

  68. Garanger E, Lecommandoux S (2012) Towards bioactive nanovehicles based on protein polymers. Angew Chem Int Ed 51:3060–3062. https://doi.org/10.1002/anie.201107734

    Article  CAS  Google Scholar 

  69. Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N (1993) Self-assembling organic nanotubes based on a cyclic peptide architecture. Nature 366:324–327. https://doi.org/10.1038/366324a0

    Article  CAS  Google Scholar 

  70. Al Samad A, De Winter J, Gerbaux P, Jerome C, Debuigne A (2017) Unique alternating peptide–peptoid copolymers from dipeptides via a Ugi reaction in water. Chem Commun 53:12240–12243. https://doi.org/10.1039/C7CC06463B

    Article  CAS  Google Scholar 

  71. Schneider JP, Pochan DJ, Ozbas B, Rajagopal K, Pakstis L, Kretsinger J (2002) Responsive hydrogels from the intramolecular folding and self-assembly of a designed peptide. J Am Chem Soc 124:15030–15037. https://doi.org/10.1021/ja027993g

    Article  CAS  Google Scholar 

  72. Pochan DJ, Schneider JP, Kretsinger J, Ozbas B, Rajagopal K, Haines L (2003) Thermally reversible hydrogels via intramolecular folding and consequent self-assembly of a de novo designed peptide. J Am Chem Soc 125:11802–11803. https://doi.org/10.1021/ja0353154

    Article  CAS  Google Scholar 

  73. Ozbas B, Kretsinger J, Rajagopal K, Schneider JP, Pochan DJ (2004) Salt-triggered peptide folding and consequent self-assembly into hydrogels with tunable modulus. Macromolecules 37:7331–7337. https://doi.org/10.1021/ma0491762

    Article  CAS  Google Scholar 

  74. Kretsinger JK, Haines LA, Ozbas B, Pochan DJ, Schneider JP (2005) Cytocompatibility of self-assembled β-hairpin peptide hydrogel surfaces. Biomaterials 26:5177–5186. https://doi.org/10.1016/j.biomaterials.2005.01.029

    Article  CAS  Google Scholar 

  75. Frisch H, Besenius P (2015) pH-Switchable self-assembled materials. Macromol Rapid Commun 36:346–363. https://doi.org/10.1002/marc.201400623

    Article  CAS  Google Scholar 

  76. Frisch H, Nie Y, Raunser S, Besenius P (2015) pH-Regulated selectivity in supramolecular polymerizations: switching between co- and homopolymers. Chem Eur J 21:3304–3309. https://doi.org/10.1002/chem.201406281

    Article  CAS  Google Scholar 

  77. Ebert G, Kuroyanagi Y (1982) Salt effect on the conformation of an alternating copolymer of L-leucine and L-lysine. Polymer 23:1154–1158. https://doi.org/10.1016/0032-3861(82)90370-6

    Article  CAS  Google Scholar 

  78. Higuchi M, Nagata K, Abiko S, Tanaka M, Kinoshita T (2008) Stimuli induced structural changes of gold nanoparticle assemblies having sequential alternating amphiphilic peptides at the surface. Langmuir 24:13359–13363. https://doi.org/10.1021/la802527n

    Article  CAS  Google Scholar 

  79. Grieshaber SE, Farran AJE, Lin-Gibson S, Kiick KL, Jia X (2009) Synthesis and characterization of elastin–mimetic hybrid polymers with multiblock, alternating molecular architecture and elastomeric properties. Macromolecules 42:2532–2541. https://doi.org/10.1021/ma802791z

    Article  CAS  Google Scholar 

  80. Grieshaber SE, Nie T, Yan C, Zhong S, Teller SS, Clifton RJ, Pochan DJ, Kiick KL, Jia X (2011) Assembly properties of an alanine-rich, lysine-containing peptide and the formation of peptide/polymer hybrid hydrogels. Macromol Chem Phys 212:229–239. https://doi.org/10.1002/macp.201000446

    Article  CAS  Google Scholar 

  81. Kricheldorf HR, Hauser K (2001) Polylactones, 45. Homo- and copolymerizations of 3-methylmorpholine-2,5-dione initiated with a cyclic tin alkoxide. Macromol Chem Phys 202:1219–1226. https://doi.org/10.1002/1521-3935(20010401)202:7%3c1219:AID-MACP1219%3e3.0.CO;2-U

    Article  CAS  Google Scholar 

  82. Feng Y, Guo J (2009) Biodegradable polydepsipeptides. Int J Mol Sci 10:589–615. https://doi.org/10.3390/ijms10020589

    Article  CAS  Google Scholar 

  83. Franz N, Klok H-A (2010) Synthesis of functional polydepsipeptides via direct ring-opening polymerization and post-polymerization modification. Macromol Chem Phys 211:809–820. https://doi.org/10.1002/macp.200900521

    Article  CAS  Google Scholar 

  84. Ouchi T, Hamada A, Ohya Y (1999) Biodegradable microspheres having reactive groups prepared from L-lactic acid-depsipeptide copolymers. Macromol Chem Phys 200:436–441. https://doi.org/10.1002/(SICI)1521-3935(19990201)200:2%3c436:AID-MACP436%3e3.0.CO;2-6

    Article  CAS  Google Scholar 

  85. Ouchi T, Toyohara M, Arimura H, Ohya Y (2002) Preparation of poly(L-lactide)-based microspheres having a cationic or anionic surface using biodegradable surfactants. Biomacromolecules 3:885–888. https://doi.org/10.1021/bm0200231

    Article  CAS  Google Scholar 

  86. He Y, Du YR, Liu XB (2011) Synthesis, characterization and properties of polyesteramides based on ε-caprolactone and 6-aminocaproic acid. Adv Mat Res 287–290:1538–1547. https://doi.org/10.4028/www.scientific.net/AMR.287-290.1538

    Article  CAS  Google Scholar 

  87. Qian Z, He Y, Zou Y, Li S, Liu X (2004) Structure and property study of degradable polyesteramide fibres: processing and alkaline degradation behaviour. Polym Degrad Stab 83:127–132. https://doi.org/10.1016/S0141-3910(03)00233-7

    Article  CAS  Google Scholar 

  88. Ali Mohamed A, Salhi S, Abid S, El Gharbi R, Fradet A (2014) Random and quasi-alternating polyesteramides deriving from ε-caprolactone and β-alanine. Eur Polym J 53:160–170. https://doi.org/10.1016/j.eurpolymj.2014.01.023

    Article  CAS  Google Scholar 

  89. Tsuji H (2016) Poly(lactic acid) stereocomplexes: a decade of progress. Adv Drug Deliv Rev 107:97–135. https://doi.org/10.1016/j.addr.2016.04.017

    Article  CAS  Google Scholar 

  90. Tsuji H, Sato S, Masaki N, Arakawa Y, Kuzuya A, Ohya Y (2018) Synthesis, stereocomplex crystallization and homo-crystallization of enantiomeric poly(lactic acid-co-alanine)s with ester and amide linkages. Polym Chem 9:565–575. https://doi.org/10.1039/C7PY02024D

    Article  CAS  Google Scholar 

  91. Matsui H, Ueda M, Makino A, Kimura S (2012) Molecular assembly composed of a dendrimer template and block polypeptides through stereocomplex formation. Chem Commun 48:6181–6183. https://doi.org/10.1039/C2CC30926B

    Article  CAS  Google Scholar 

  92. Ueda M, Makino A, Imai T, Sugiyama J, Kimura S (2011) Transformation of peptide nanotubes into a vesicle via fusion driven by stereo-complex formation. Chem Commun 47:3204–3206. https://doi.org/10.1039/C0CC04209A

    Article  CAS  Google Scholar 

  93. Ueda M, Makino A, Imai T, Sugiyama J, Kimura S (2011) Tubulation on peptide vesicles by phase-separation of a binary mixture of amphiphilic right-handed and left-handed helical peptides. Soft Matter 7:4143–4146. https://doi.org/10.1039/C0SM01308K

    Article  CAS  Google Scholar 

  94. Grieshaber SE, Paik BA, Bai S, Kiick KL, Jia X (2013) Nanoparticle formation from hybrid, multiblock copolymers of poly(acrylic acid) and a VPGVG peptide. Soft Matter 9:1589–1599. https://doi.org/10.1039/C2SM27496E

    Article  CAS  Google Scholar 

  95. Graña-Suárez L, Verboom W, Buckle T, Rood M, van Leeuwen FWB, Huskens J (2016) Loading and release of fluorescent oligoarginine peptides into/from pH-responsive anionic supramolecular nanoparticles. J Mater Chem B 4:4025–4032. https://doi.org/10.1039/C6TB00933F

    Article  CAS  Google Scholar 

  96. Zhou C, Yuan Y, Zhou P, Wang F, Hong Y, Wang N, Xu S, Du J (2017) Highly effective antibacterial vesicles based on peptide-mimetic alternating copolymers for bone repair. Biomacromolecules 18:4154–4162. https://doi.org/10.1021/acs.biomac.7b01209

    Article  CAS  Google Scholar 

  97. Bauri K, Saha B, Mahanti J, De P (2017) A nonconjugated macromolecular luminogen for speedy, selective and sensitive detection of picric acid in water. Polym Chem 8:7180–7187. https://doi.org/10.1039/C7PY01579H

    Article  CAS  Google Scholar 

  98. Srichan S, Chan-Seng D, Lutz J-F (2012) Influence of strong electron-donor monomers in sequence-controlled polymerizations. ACS Macro Lett 1:589–592. https://doi.org/10.1021/mz3001513

    Article  CAS  Google Scholar 

  99. Jia Y-G, Liu L-Y, Lei B, Li J, Zhu XX (2011) Crown ether cavity-containing copolymers via controlled alternating cyclocopolymerization. Macromolecules 44:6311–6317. https://doi.org/10.1021/ma201247d

    Article  CAS  Google Scholar 

  100. Heravi MM, Hashemi E, Beheshtiha YS, Kamjou K, Toolabi M, Hosseintash N (2014) Solvent-free multicomponent reactions using the novel N-sulfonic acid modified poly(styrene-maleic anhydride) as a solid acid catalyst. J Mol Catal A-Chem 392:173–180. https://doi.org/10.1016/j.molcata.2014.04.024

    Article  CAS  Google Scholar 

  101. Heravi MM, Hashemi E, Beheshtiha YS, Ahmadi S, Hosseinnejad T (2014) PdCl2 on modified poly(styrene-co-maleic anhydride): a highly active and recyclable catalyst for the Suzuki–Miyaura and Sonogashira reactions. J Mol Catal A-Chem 394:74–82. https://doi.org/10.1016/j.molcata.2014.07.001

    Article  CAS  Google Scholar 

  102. Soer WJ, Ming W, Klumperman B, Koning C, van Benthem R (2006) Surfactant-free artificial latexes from modified styrene–maleic anhydride (SMA) copolymers. Polymer 47:7621–7627. https://doi.org/10.1016/j.polymer.2006.09.007

    Article  CAS  Google Scholar 

  103. Baranello MP, Bauer L, Benoit DSW (2014) Poly(styrene-alt-maleic anhydride)-based diblock copolymer micelles exhibit versatile hydrophobic drug loading, drug-dependent release, and internalization by multidrug resistant ovarian cancer cells. Biomacromolecules 15:2629–2641. https://doi.org/10.1021/bm500468d

    Article  CAS  Google Scholar 

  104. Lazzara TD, van de Ven TGM, Whitehead MA (2008) Nanotube self-assembly of a styrene and maleimide alternating copolymer. Macromolecules 41:6747–6751. https://doi.org/10.1021/ma800926a

    Article  CAS  Google Scholar 

  105. Wang Z, Gao M, Sun J, Liang D, Jia X (2013) Photoresponsive dendronized copolymers of styrene and maleic anhydride pendant with poly(amidoamine) dendrons as side groups. Macromolecules 46:1723–1731. https://doi.org/10.1021/ma302358t

    Article  CAS  Google Scholar 

  106. Zhang Z, Hong L, Gao Y, Zhang W (2014) One-pot synthesis of POSS-containing alternating copolymers by RAFT polymerization and their microphase-separated nanostructures. Polym Chem 5:4534–4541. https://doi.org/10.1039/C4PY00302K

    Article  CAS  Google Scholar 

  107. Zhang Z, Hong L, Li J, Liu F, Cai H, Gao Y, Zhang W (2015) One-pot synthesis of well-defined amphiphilic alternating copolymer brushes based on POSS and their self-assembly in aqueous solution. RSC Adv 5:21580–21587. https://doi.org/10.1039/C4RA15492D

    Article  CAS  Google Scholar 

  108. Srichan S, Oswald L, Zamfir M, Lutz J-F (2012) Precision polyelectrolytes. Chem Commun 48:1517–1519. https://doi.org/10.1039/C1CC14823K

    Article  CAS  Google Scholar 

  109. Srichan S, Kayunkid N, Oswald L, Lotz B, Lutz J-F (2014) Synthesis and characterization of sequence-controlled semicrystalline comb copolymers: influence of primary structure on materials properties. Macromolecules 47:1570–1577. https://doi.org/10.1021/ma4023179

    Article  CAS  Google Scholar 

  110. Baradel N, Gok O, Zamfir M, Sanyal A, Lutz J-F (2013) Sequence-controlled polymerization using dendritic macromonomers: precise chain-positioning of bulky functional clusters. Chem Commun 49:7280–7282. https://doi.org/10.1039/C3CC43501F

    Article  CAS  Google Scholar 

  111. Li Y, Mao M, Matolyak LE, Turner SR (2012) Sterically crowded anionic polyelectrolytes with tunable charge densities based on stilbene-containing copolymers. ACS Macro Lett 1:257–260. https://doi.org/10.1021/mz200061w

    Article  CAS  Google Scholar 

  112. Li Y, Savage AM, Zhou X, Turner SR, Davis RM (2013) Solution properties of stilbene-containing sterically crowded alternating polyanions. J Polym Sci Part B Polym Phys 51:1565–1570. https://doi.org/10.1002/polb.23370

    Article  CAS  Google Scholar 

  113. O’Shea J-P, Solovyeva V, Guo X, Zhao J, Hadjichristidis N, Rodionov VO (2014) Sequence-controlled copolymers of 2,3,4,5-pentafluorostyrene: mechanistic insight and application to organocatalysis. Polym Chem 5:698–701. https://doi.org/10.1039/C3PY01368E

    Article  Google Scholar 

  114. Huang J, Zhou X, Lamprou A, Maya F, Svec F, Turner SR (2015) Nanoporous polymers from cross-linked polymer precursors via tert-butyl group deprotection and their carbon dioxide capture properties. Chem Mater 27:7388–7394. https://doi.org/10.1021/acs.chemmater.5b03114

    Article  CAS  Google Scholar 

  115. Zhou X, Huang J, Barr KW, Lin Z, Maya F, Abbott LJ, Colina CM, Svec F, Turner SR (2015) Nanoporous hypercrosslinked polymers containing Tg enhancing comonomers. Polymer 59:42–48. https://doi.org/10.1016/j.polymer.2014.12.065

    Article  CAS  Google Scholar 

  116. Tang D, Jiang X, Liu H, Li C, Zhao Y (2014) Synthesis and properties of heterografted toothbrush-like copolymers with alternating PEG and PCL grafts and tunable RAFT-generated segments. Polym Chem 5:4679–4692. https://doi.org/10.1039/C4PY00332B

    Article  CAS  Google Scholar 

  117. Ping J, Gu K, Zhou S, Pan H, Shen Z, Fan X-H (2016) Hierarchically self-assembled amphiphilic alternating copolymer brush containing side-chain cholesteryl units. Macromolecules 49:5993–6000. https://doi.org/10.1021/acs.macromol.6b01043

    Article  CAS  Google Scholar 

  118. Ping J, Pan Y, Pan H, Wu B, Zhou H, Shen Z, Fan X-H (2015) Microphase separation and high ionic conductivity at high temperatures of lithium salt-doped amphiphilic alternating copolymer brush with rigid side chains. Macromolecules 48:8557–8564. https://doi.org/10.1021/acs.macromol.5b01678

    Article  CAS  Google Scholar 

  119. Tsujii A, Namba M, Okamura H, Matsumoto A (2014) Radical alternating copolymerization of twisted 1,3-butadienes with maleic anhydride as a new approach for degradable thermosetting resin. Macromolecules 47:6619–6626. https://doi.org/10.1021/ma501555n

    Article  CAS  Google Scholar 

  120. Kim H, Kang YJ, Jeong ES, Kang S, Kim KT (2012) Glucose-responsive disassembly of polymersomes of sequence-specific boroxole-containing block copolymers under physiologically relevant conditions. ACS Macro Lett 1:1194–1198. https://doi.org/10.1021/mz3004192

    Article  CAS  Google Scholar 

  121. Yang P, Mykhaylyk OO, Jones ER, Armes SP (2016) RAFT dispersion alternating copolymerization of styrene with N-phenylmaleimide: morphology control and application as an aqueous foam stabilizer. Macromolecules 49:6731–6742. https://doi.org/10.1021/acs.macromol.6b01563

    Article  CAS  Google Scholar 

  122. Reches M, Gazit E (2003) Casting metal nanowires within discrete self-assembled peptide nanotubes. Science 300:625–627. https://doi.org/10.1126/science.1082387

    Article  CAS  Google Scholar 

  123. Chen J, Yu C, Shi Z, Yu S, Lu Z, Jiang W, Zhang M, He W, Zhou Y, Yan D (2015) Ultrathin alternating copolymer nanotubes with readily tunable surface functionalities. Angew Chem 127:3692–3696. https://doi.org/10.1002/ange.201408290

    Article  Google Scholar 

  124. Adler-Abramovich L, Gazit E (2014) The physical properties of supramolecular peptide assemblies: from building block association to technological applications. Chem Soc Rev 43:6881–6893. https://doi.org/10.1039/C4CS00164H

    Article  CAS  Google Scholar 

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Acknowledgements

I. M. and K. G. G. acknowledge Council of Scientific and Industrial Research (CSIR), Government of India, India, for their research fellowships.

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Mukherjee, I., Goswami, K.G., De, P. (2020). Alternating Copolymers Based on Amino Acids and Peptides. In: Katiyar, V., Kumar, A., Mulchandani, N. (eds) Advances in Sustainable Polymers. Materials Horizons: From Nature to Nanomaterials. Springer, Singapore. https://doi.org/10.1007/978-981-15-1251-3_5

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