Chemical strategies for the synthesis of protein-polymer conjugates

Advances in Polymer Science

Volumn 253, Issue , 2013, Pages 37-70

  Jung, Björn ^a   Theato, Patrick ^b  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Biomaterials; Click chemistry; Peptides; Polymer conjugate; Protein modification; Proteins

Indexed keywords

EID: 84873547128     PISSN: 00653195     EISSN: None     Source Type: Book Series    
DOI: 10.1007/12_2012_169     Document Type: Article

References (171)

1. Klok H (2009) Peptide/protein-synthetic polymer conjugates: Quo vadis. Macromolecules 42:7990-8000
2. Badi N, Lutz J (2009) Sequence control in polymer synthesis. Chem Soc Rev 38:3383-3390
3. Lutz J (2010) Polymer chemistry: A controlled sequence of events. Nat Chem 2:84-85
4. Lutz J (2010) Sequence-controlled polymerizations: The next Holy Grail in polymer sciencë Polym Chem 1:55-62
5. Kiick KL (2007) Polymer therapeutics. Science 317:1182-1183
6. Liu S, Maheshwari R, Kiick KL (2009) Polymer-based therapeutics. Macromolecules 42:3-13
7. Leader B, Baca QJ, Golan DE (2008) Protein therapeutics: A summary and pharmacological classification. Nat Rev Drug Discov 7:21-39
8. Caliceti P, Veronese FM (2003) Pharmacokinetic and biodistribution properties of poly (ethylene glycol)-protein conjugates. Adv Drug Deliv Rev 55:1261-1277 (Pubitemid 37464561)
9. Schellekens H (2002) Bioequivalence and the immunogenicity of biopharmaceuticals. Nat Rev Drug Discov 1:457-462 (Pubitemid 37361488)
10. de Groot AS, Scott DW (2007) Immunogenicity of protein therapeutics. Trends Immunol 28:482-490 (Pubitemid 350087812)
11. Kontermann RE (2011) Strategies for extended serum half-life of protein therapeutics. Curr Opin Chem Biol 22:868-876
12. Lao BJ, Kamei DT (2008) Improving therapeutic properties of protein drugs through alteration of intracellular trafficking pathways. Biotechnol Prog 24:2-7 (Pubitemid 351231243)
13. Pasut G, Veronese F (2007) Polymer-drug conjugation, recent achievements and general strategies. Prog Polym Sci 32:933-961 (Pubitemid 47198290)
14. Harris JM, Chess RB (2003) Effect of pegylation on pharmaceuticals. Nat Rev Drug Discov 2:214-221 (Pubitemid 37361666)
15. Duncan R (2006) Polymer conjugates as anticancer nanomedicines. Nat Rev Cancer 6:688-701 (Pubitemid 44286001)
16. Pasut G, Sergi M, Veronese FM (2008) Anti-cancer PEG-enzymes: 30 years old, but still a current approach. Adv Drug Deliv Rev 60:69-78 (Pubitemid 350181167)
17. Ryan SM, Mantovani G, Wang X, Haddleton DM, Brayden DJ (2008) Advances in PEGylation of important biotech molecules: Delivery aspects. Expert Opin Drug Deliv 5:371-383 (Pubitemid 351721718)
18. Maeda H, Bharate GY, Daruwalla J (2009) Polymeric drugs for efficient tumor-Targeted drug delivery based on EPR-effect. Eur J Pharm Biopharm 71:409-419
19. Vandermeulen GW, Klok H (2004) Peptide/protein hybrid materials: Enhanced control of structure and improved performance through conjugation of biological and synthetic polymers. Macromol Biosci 4:383-398 (Pubitemid 39257162)
20. Peer D, Karp JM, Hong S, Farokhzad OC, Margalit R, Langer R (2007) Nanocarriers as an emerging platform for cancer therapy. Nat Nanotechnol 2:751-760 (Pubitemid 350223348)
21. Maeda H (2001) SMANCS and polymer-conjugated macromolecular drugs: Advantages in cancer chemotherapy. Adv Drug Deliv Rev 46:169-185
22. Matsumura Y, Maeda H (1986) A new concept for macromolecular therapeutics in cancer chemotherapy: Mechanism of tumoritropic accumulation of proteins and the antitumor agent SMANCS. Cancer Res 46:6387-6392 (Pubitemid 17221789)
23. Graham M (2003) Pegaspargase: A review of clinical studies. Adv Drug Deliv Rev 55:1293-1302 (Pubitemid 37464563)
24. Reddy KR, Modi MW, Pedder S (2002) Use of peginterferon alfa-2a (40 KD) (Pegasys®) for the treatment of hepatitis C. Adv Drug Deliv Rev 54:571-586 (Pubitemid 34615548)
25. Wang Y, Youngster S, Grace M, Bausch J, Bordens R, Wyss DF (2002) Structural and biological characterization of pegylated recombinant interferon alpha-2b and its therapeutic implications. Adv Drug Deliv Rev 54:547-570 (Pubitemid 34618512)
26. Duncan R, Ringsdorf H, Satchi-Fainaro R (2006) Polymer therapeutics: Polymers as drugs, drug and protein conjugates and gene delivery systems: Past, present and future opportunities. Adv Polym Sci 192:1-8
27. Vicent MJ, Dieudonné L, Carbajo RJ, Pineda-Lucena A (2008) Polymer conjugates as therapeutics: Future trends, challenges and opportunities. Expert Opin Drug Deliv 5:593-614 (Pubitemid 351888105)
28. Alconcel SN, Baas AS, Maynard HD (2011) FDA-Approved poly(ethylene glycol)-protein conjugate drugs. Polym Chem 2:1442-1448
29. Thordarson P, Droumaguet B, Velonia K (2006) Well-defined protein-polymer conjugates - Synthesis and potential applications. Appl Microbiol Biotechnol 73:243-254 (Pubitemid 350262602)
30. Shakya AK, Sami H, Srivastava A, Kumar A (2010) Stability of responsive polymer-protein bioconjugates. Prog Polym Sci 35:459-486
31. Dagani R (1995) Polymeric 'smart' materials respond to changes in their environment. Chem Eng News 73:30-33
32. Hoffman AS, Stayton PS (2004) Bioconjugates of smart polymers and proteins: Synthesis and applications. Macromol Symp 207:139-152
33. Hoffman AS, Stayton PS (2007) Conjugates of stimuli-responsive polymers and proteins. Prog Polym Sci 32:922-932 (Pubitemid 47198289)
34. Schmaljohann D (2006) Thermo- And pH-responsive polymers in drug delivery. Adv Drug Deliv Rev 58:1655-1670 (Pubitemid 44830149)
35. Zarafshani Z, Obata T, Lutz J (2010) Smart PEGylation of trypsin. Biomacromolecules 11:2130-2135
36. Hentschel J, Bleek K, Ernst O, Lutz J, Börner HG (2008) Easy access to bioactive peptide-polymer conjugates via RAFT. Macromolecules 41:1073-1075 (Pubitemid 351363104)
37. Ding Z, Fong RB, Long CJ, Stayton PS, Hoffman AS (2001) Size-dependent control of the binding of biotinylated proteins to streptavidin using a polymer shield. Nature 411:59-62 (Pubitemid 32428187)
38. Shimoboji T, Larenas E, Fowler T, Kulkarni S, Hoffman AS, Stayton PS (2002) Photoresponsive polymer-enzyme switches. PNAS 99:16592-16596 (Pubitemid 36034017)
39. Ding Z, Chen G, Hoffman AS (1998) Unusual properties of thermally sensitive oligomer-enzyme conjugates of poly(N-isopropylacrylamide)-Trypsin. J Biomed Mater Res 39:498-505 (Pubitemid 28063469)
40. Li H, Bapat AP, Li M, Sumerlin BS (2011) Protein conjugation of thermoresponsive aminereactive polymers prepared by RAFT. Polym Chem 2:323-327
41. Reynhout IC, Cornelissen JJ, Nolte RJ (2009) Synthesis of polymer-biohybrids: From small to giant surfactants. Acc Chem Res 42:681-692
42. Velonia K (2010) Protein-polymer amphiphilic chimeras: Recent advances and future challenges. Polym Chem 1:944-952
43. Boerakker MJ, Hannink JM, Bomans PH, Frederik PM, Nolte RJ, Meijer EM, Sommerdijk NA (2002) Giant amphiphiles by cofactor reconstitution. Angew Chem Int Ed 41:4239-4241 (Pubitemid 35398242)
44. Uludag H, Norrie B, Kousinioris N, Gao T (2001) Engineering temperature-sensitive poly(Nisopropylacrylamide) polymers as carriers of therapeutic proteins. Biotechnol Bioeng 73:510-521 (Pubitemid 32574326)
45. Haag R, Kratz F (2006) Polymer therapeutics: Concepts and applications. Angew Chem Int Ed 45:1198-1215 (Pubitemid 44097641)
46. Godwin A, Bolina KC, Dinand E, Rankin S, Simic S, Brocchini S (2001) Strategies for polymer development in pharmaceutical science - A short review. J Pharm Pharmacol 53:1175-1184 (Pubitemid 32904011)
47. Duncan R (2003) The dawning era of polymer therapeutics. Nat Rev Drug Discov 2:347-360 (Pubitemid 37361705)
48. de Alarco'n Cl, Pennadam S, Alexander C (2005) Stimuli responsive polymers for biomedical applications. Chem Soc Rev 34:276-285 (Pubitemid 40444408)
49. Bajpai A, Shukla SK, Bhanu S, Kankane S (2008) Responsive polymers in controlled drug delivery. Prog Polym Sci 33:1088-1118
50. Schild H (1992) Poly(N-isopropylacrylamide): Experiment, theory and application. Prog Polym Sci 17:163-249
51. Bütün V, Liu S, Weaver J, Bories-Azeau X, Cai Y, Armes S (2006) A brief review of 'schizophrenic' block copolymers. React Funct Polym 66:157-165 (Pubitemid 41745500)
52. Smith AE, Xu X, Kirkland-York SE, Savin DA, McCormick CL (2010) "Schizophrenic" selfassembly of block copolymers synthesized via aqueous RAFT polymerization: From micelles to vesicles. Macromolecules 43:1210-1217
53. Du J, O'Reilly RK (2010) pH-responsive vesicles from a schizophrenic diblock copolymer. Macromol Chem Phys 211:1530-1537
54. Link AJ, Vink MK, Tirrell DA (2007) Synthesis of the functionalizable methionine surrogate azidohomoalanine using Boc-homoserine as precursor. Nat Protoc 2:1884-1887 (Pubitemid 47308127)
55. Montclare JK, Tirrell DA (2006) Evolving proteins of novel composition. Angew Chem Int Ed 45:4518-4521 (Pubitemid 44105626)
56. Gauthier MA, Klok H (2008) Peptide/protein-polymer conjugates: Synthetic strategies and design concepts. Chem Commun 2591-2611 (Pubitemid 351793824)
57. Espuña G, Arsequell G, Valencia G, Barluenga J, Alvarez-Gutiérrez JM, Ballesteros A, González JM (2004) Regioselective postsynthetic modification of phenylalanine side chains of peptides leading to uncommon ortho-iodinated analogues. Angew Chem Int Ed 43:325-329 (Pubitemid 38090068)
58. Tam JP, Xu J, Eom KD (2001) Methods and strategies of peptide ligation. Biopolymers 60:194-205 (Pubitemid 34074173)
59. Villar HO, Koehler RT (2000) Amino acid preferences of small, naturally occurring polypeptides. Biopolymers 53:226-232 (Pubitemid 30082309)
60. Villar HO, Kauvar LM (1994) Amino acid preferences at protein binding sites. FEBS Lett 349:125-130 (Pubitemid 24230235)
61. UniProt Database. UniProtKB/Swiss-Prot protein knowledgebase release 2011-09 statistics. http://expasy.org
62. Moelbert S, Emberly E, Tang C (2004) Correlation between sequence hydrophobicity and surface-exposure pattern of database proteins. Protein Sci 13:752-762 (Pubitemid 38252572)
63. Antos JM, McFarland JM, Iavarone AT, Francis MB (2009) Chemoselective tryptophan labeling with rhodium carbenoids at mild pH. J Am Chem Soc 131:6301-6308
64. Grover GN, Maynard HD (2010) Protein-polymer conjugates: Synthetic approaches by controlled radical polymerizations and interesting applications. Curr Opin Chem Biol 14:818-827
65. Broyer RM, Grover GN, Maynard HD (2011) Emerging synthetic approaches for protein-polymer conjugations. Chem Commun 47:2212-2226
66. Gauthier MA, Klok H (2010) Polymer-protein conjugates: An enzymatic activity perspective. Polym Chem 1:1352
67. Tasdelen MA, Kahveci MU, Yagci Y (2011) Telechelic polymers by living and controlled/ living polymerization methods. Prog Polym Sci 36:455-567
68. Willcock H, O'Reilly RK (2010) End group removal and modification of RAFT polymers. Polym Chem 1:149-157
69. Stukel JM, Li RC, Maynard HD, Caplan MR (2010) Two-step synthesis of multivalent cancer-Targeting constructs. Biomacromolecules 11:160-167
70. Nicolas J, Mantovani G, Haddleton DM (2007) Living radical polymerization as a tool for the synthesis of polymer-protein/peptide bioconjugates. Macromol Rapid Commun 28:1083-1111 (Pubitemid 47252039)
71. Barner-Kowollik C (2008) Handbook of RAFT polymerization. Wiley-VCH, Weinheim
72. Moad G, Rizzardo E, Thang SH (2005) Living radical polymerization by the RAFT process. Aust J Chem 58:379-410 (Pubitemid 41028303)
73. Favier A, Charreyre M (2006) Experimental requirements for an efficient control of freeradical polymerizations via the reversible addition-fragmentation chain transfer (RAFT) process. Macromol Rapid Commun 27:653-692 (Pubitemid 43759868)
74. Boyer C, Stenzel MH, Davis TP (2011) Building nanostructures using RAFT polymerization. J Polym Sci A Polym Chem 49:551-595
75. Patten TE, Matyjaszewski K (1998) Atom transfer radical polymerization and the synthesis of polymeric materials. Adv Mater 10:901-915 (Pubitemid 128539708)
76. Matyjaszewski K, Xia J (2001) Atom transfer radical polymerization. Chem Rev 101:2921-2990 (Pubitemid 35377809)
77. Matyjaszewski K, Tsarevsky NV (2009) Nanostructured functional materials prepared by atom transfer radical polymerization. Nat Chem 1:276-288
78. Sciannamea V, Je'rôme R, Detrembleur C (2008) In-situ nitroxide-mediated radical polymerization (NMP) processes: Their understanding and optimization. Chem Rev 108:1104-1126 (Pubitemid 351577857)
79. Veronese FM, Pasut G (2005) PEGylation, successful approach to drug delivery. Drug Discov Today 10:1451-1458 (Pubitemid 41483874)
80. Fee CJ, van Alstine JM (2006) PEG-proteins: Reaction engineering and separation issues. Chem Eng Sci 61:924-939
81. Klok H (2005) Biological-synthetic hybrid block copolymers: Combining the best from two worlds. J Polym Sci A Polym Chem 43:1-17 (Pubitemid 40049960)
82. Kinstler OB, Brems DN, Lauren SL, Paige AG, Hamburger JB, Treuheit MJ (1996) Characterization and stability of N-Terminally PEGylated rhG-CSF. Pharm Res 13:996-1002 (Pubitemid 26258997)
83. Mougin NC, van Rijn P, Park H, Müller AH, Böker A (2011) Hybrid capsules via selfassembly of thermoresponsive and interfacially active bionanoparticle-polymer conjugates. Adv Funct Mater 21:2470-2476
84. Lecolley F, Tao L, Mantovani G, Durkin I, Lautru S, Haddleton DM (2004) A new approach to bioconjugates for proteins and peptides ("pegylation" ) utilising living radical polymerisation. Chem Commun 2026. Electronic supplementary information (ESI) available: Experimental procedures on prepared compounds and characterisation. See http://www.rsc. org/suppdata/cc/b4/b407712a
85. Ladmiral V, Monaghan L, Mantovani G, Haddleton DM (2005) a-Functional glycopolymers: New materials for (poly)peptide conjugation. Polymer 46:8536-8545 (Pubitemid 41203078)
86. Miyamoto D, Watanabe J, Ishihara K (2004) Highly stabilized papain conjugated with watersoluble phospholipid polymer chain having a reacting terminal group. J Appl Polym Sci 91:827-832 (Pubitemid 37539384)
87. Roberts MJ, Bentley MD, Harris JM (2002) Chemistry for peptide and protein PEGylation. Adv Drug Deliv Rev 54:459-476 (Pubitemid 34615543)
88. Harris JM, Kozlowski A. Poly(ethylene glycol) and related polymers monosubstituted with propionic or butanoic acids and functional derivatives thereof for biotechnical applications. Patent 5672662
89. Basu A, Yang K, Wang M, Liu S, Chintala R, Palm T, Zhao H, Peng P, Wu D, Zhang Z, Hua J, Hsieh M, Zhou J, Petti G, Li X, Janjua A, Mendez M, Liu J, Longley C, Zhang Z, Mehlig M, Borowski V, Viswanathan M, Filpula D (2006) Structure-function engineering of interferon-b-1b for improving stability, solubility, potency, immunogenicity, and pharmacokinetic properties by site-selective mono-PEGylation. Bioconjugate Chem 17:618-630 (Pubitemid 43794371)
90. Magnusson JP, Bersani S, Salmaso S, Alexander C, Caliceti P (2010) In situ growth of sidechain PEG polymers from functionalized human growth hormone - A new technique for preparation of enhanced protein-polymer conjugates. Bioconjugate Chem 21:671-678
91. Pasut G,Mero A, Caboi F, Scaramuzza S, Sollai L, Veronese FM (2008) A new PEG-b-Alanine active derivative for releasable protein conjugation. Bioconjugate Chem 19:2427-2431
92. Tao L, Liu J, Davis TP (2009) Branched polymer-protein conjugates made from mid-chainfunctional P(HPMA). Biomacromolecules 10:2847-2851
93. Wiss KT, Krishna OD, Roth PJ, Kiick KL, Theato P (2009) A versatile grafting-To approach for the bioconjugation of polymers to collagen-like peptides using an activated ester chain transfer agent. Macromolecules 42:3860-3863
94. Roth PJ, Wiss KT, Zentel R, Theato P (2008) Synthesis of reactive telechelic polymers based on pentafluorophenyl esters. Macromolecules 41:8513-8519
95. Roth PJ, Jochum FD, Zentel R, Theato P (2010) Synthesis of hetero-Telechelic a, o biofunctionalized polymers. Biomacromolecules 11:238-244
96. Apostolovic B, Deacon SP, Duncan R, Klok H (2010) Hybrid polymer therapeutics incorporating bioresponsive, coiled coil peptide linkers. Biomacromolecules 11:1187-1195
97. Apostolovic B, Klok H (2010) Copolymerization behavior of N-(2-hydroxypropyl) methacrylamide and a methacrylated coiled-coil peptide derivative. Biomacromolecules 11:1891-1895
98. Lele BS, Murata H, Matyjaszewski K, Russell AJ (2005) Synthesis of uniform protein-polymer conjugates. Biomacromolecules 6:3380-3387 (Pubitemid 41764102)
99. Zhang J, Lei Y, Dhaliwal A, Ng QK, Du J, Yan M, Lu Y, Segura T (2011) Protein-polymer nanoparticles for nonviral gene delivery. Biomacromolecules 12:1006-1014
100. Thilakarathne V, Briand VA, Zhou Y, KasiRM, Kumar CV (2011) Protein polymer conjugates: Improving the stability of hemoglobin with poly(acrylic acid). Langmuir 27:7663-7671
101. Tao L, Mantovani G, Lecolley F, Haddleton DM (2004) a-Aldehyde terminally functional methacrylic polymers from living radical polymerization: Application in protein conjugation "pegylation". J Am Chem Soc 126:13220-13221 (Pubitemid 39382738)
102. Sayers CT, Mantovani G, Ryan SM, Randev RK, Keiper O, Leszczyszyn OI, Blindauer C, Brayden DJ, Haddleton DM (2009) Site-specific N-Terminus conjugation of poly (mPEG1100) methacrylates to salmon calcitonin: Synthesis and preliminary biological evaluation. Soft Matter 5:3038
103. McFarland JM, Francis MB (2005) Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation. J Am Chem Soc 127:13490-13491 (Pubitemid 41401189)
104. van Maarseveen JH, Reek JN, Back JW (2006) Transition-metal catalysis as a tool for the covalent labeling of proteins. Angew Chem Int Ed 45:1841-1843 (Pubitemid 44105202)
105. Levesque G, Arsène P, Fanneau-Bellenger V, Pham T (2000) Protein thioacylation. 1. Reagents design and synthesis. Biomacromolecules 1:387-399
106. Lundblad RL (1995) Techniques in protein modification. CRC, Boca Raton
107. Hermanson GT (1996) Bioconjugate techniques. Academic, San Diego
108. Murthy N, Campbell J, Fausto N, Hoffman AS, Stayton PS (2003) Bioinspired pH-responsive polymers for the intracellular delivery of biomolecular drugs. Bioconjugate Chem 14:412-419 (Pubitemid 36348665)
109. Bontempo D, Heredia KL, Fish BA, Maynard HD (2004) Cysteine-reactive polymers synthesized by atom transfer radical polymerization for conjugation to proteins. J Am Chem Soc 126:15372-15373 (Pubitemid 39577459)
110. Heredia KL, Bontempo D, Ly T, Byers JT, Halstenberg S, Maynard HD (2005) In situ preparation of protein-"smart" polymer conjugates with retention of bioactivity. J Am Chem Soc 127:16955-16960 (Pubitemid 41772855)
111. Liu J, Bulmus V, Barner-Kowollik C, Stenzel MH, Davis TP (2007) Direct synthesis of pyridyl disulfide-Terminated polymers by RAFT polymerization. Macromol Rapid Commun 28:305-314 (Pubitemid 47250614)
112. Liu J, Bulmus V, Herlambang DL, Barner-Kowollik C, Stenzel MH, Davis TP (2007) In situ formation of protein-polymer conjugates through reversible addition fragmentation chain transfer polymerization. Angew Chem 119:3159-3163
113. Boyer C, Bulmus V, Liu J, Davis TP, Stenzel MH, Barner-Kowollik C (2007) Well-defined protein-polymer conjugates via in situ RAFT polymerization. J Am Chem Soc 129:7145-7154 (Pubitemid 46903280)
114. Liu J, Liu H, Bulmus V, Tao L, Boyer C, Davis TP (2010) A simple methodology for the synthesis of heterotelechelic protein-polymer-biomolecule conjugates. J Polym Sci A Polym Chem 48:1399-1405
115. Tedaldi LM, Smith ME, Nathani RI, Baker JR (2009) Bromomaleimides: New reagents for the selective and reversible modification of cysteine. Chem Commun 6583-6585
116. Schumacher FF, Nobles M, Ryan CP, Smith ME, Tinker A, Caddick S, Baker JR (2011) In situ maleimide bridging of disulfides and a new approach to protein PEGylation. Bioconjugate Chem 22:132-136
117. Jones MW, Strickland RA, Schumacher FF, Caddick S, Baker JR, Gibson MI, Haddleton DM (2012) Polymeric dibromomaleimides as extremely efficient disulfide bridging bioconjugation and pegylation agents. J Am Chem Soc 134:1847-1852
118. Shaunak S, Godwin A, Choi J, Balan S, Pedone E, Vijayarangam D, Heidelberger S, Teo I, Zloh M, Brocchini S (2006) Site-specific PEGylation of native disulfide bonds in therapeutic proteins. Nat Chem Biol 2:312-313 (Pubitemid 43787211)
119. Balan S, Choi J, Godwin A, Teo I, Laborde CM, Heidelberger S, Zloh M, Shaunak S, Brocchini S (2007) Site-specific PEGylation of protein disulfide bonds using a three-carbon bridge. Bioconjugate Chem 18:61-76 (Pubitemid 46145995)
120. De P, Li M, Gondi SR, Sumerlin BS (2008) Temperature-regulated activity of responsive polymer-protein conjugates prepared by grafting-from via RAFT polymerization. J Am Chem Soc 130:11288-11289
121. Li M, Li H, De P, Sumerlin BS (2011) Thermoresponsive block copolymer-protein conjugates prepared by grafting-from via RAFT polymerization. Macromol Rapid Commun 32:354-359
122. Mantovani G, Lecolley F, Tao L, Haddleton DM, Clerx J, Cornelissen JJ, Velonia K (2005) Design and synthesis of N. J Am Chem Soc 127:2966-2973
123. Neubert BJ, Snider BB (2003) Synthesis of -phloeodictine A1. Org Lett 5:765-768
124. Le Droumaguet B, Mantovani G, Haddleton DM, Velonia K (2007) Formation of giant amphiphiles by post-functionalization of hydrophilic protein-polymer conjugates. J Mater Chem 17:1916-1922 (Pubitemid 46717881)
125. Geng J, Mantovani G, Tao L, Nicolas J, Chen G, Wallis R, Mitchell DA, Johnson BR, Evans SD, Haddleton DM (2007) Site-directed conjugation of "clicked" glycopolymers to form glycoprotein mimics: Binding to mammalian lectin and induction of immunological function. J Am Chem Soc 129:15156-15163 (Pubitemid 350247799)
126. Bays E, Tao L, Chang C, Maynard HD (2009) Synthesis of semitelechelic maleimide poly (PEGA) for protein conjugation by RAFT polymerization. Biomacromolecules 10:1777-1781
127. Pennadam SS, Lavigne MD, Dutta CF, Firman K, Mernagh D, Go'recki DC, Alexander C (2004) Control of a multisubunit DNA motor by a thermoresponsive polymer switch. J Am Chem Soc 126:13208-13209 (Pubitemid 39382732)
128. Perrier S, Takolpuckdee P, Mars CA (2005) Reversible addition- fragmentation chain transfer polymerization: End group modification for functionalized polymers and chain transfer agent recovery. Macromolecules 38:2033-2036 (Pubitemid 40430363)
129. Deacon SP, Apostolovic B, Carbajo RJ, Schott A, Beck K, Vicent MJ, Pineda-Lucena A, Klok H, Duncan R (2011) Polymer coiled-coil conjugates: Potential for development as a new class of therapeutic "molecular switch". Biomacromolecules 12:19-27
130. Tao L, Kaddis CS, Ogorzalek Loo RR, Grover GN, Loo JA, Maynard HD (2009) Synthetic approach to homodimeric protein-polymer conjugates. Chem Commun 2148
131. Heredia KL, Tao L, Grover GN, Maynard HD (2010) Heterotelechelic polymers for capture and release of protein-polymer conjugates. Polym Chem 1:168-170
132. Tao L, Kaddis CS, Loo RR, Grover GN, Loo JA, Maynard HD (2009) Synthesis of maleimide-end-functionalized star polymers and multimeric protein-polymer conjugates. Macromolecules 42:8028-8033
133. Li M, De P, Li H, Sumerlin BS (2010) Conjugation of RAFT-generated polymers to proteins by two consecutive thiol-ene reactions. Polym Chem 1:854-859
134. Grover GN, Alconcel SN, Matsumoto NM, Maynard HD (2009) Trapping of thiol-Terminated acrylate polymers with divinyl sulfone to generate well-defined semitelechelic Michael acceptor polymers. Macromolecules 42:7657-7663
135. Jones MW, Mantovani G, Ryan SM, Wang X, Brayden DJ, Haddleton DM (2009) Phosphinemediated one-pot thiol-ene "click" approach to polymer-protein conjugates. Chem Commun 5272-5274
136. Valdebenito A, Espinoza P, Lissi E, Encinas M (2010) Bovine serum albumin as chain transfer agent in the acrylamide polymerization. Protein-polymer conjugates. Polymer 51:2503-2507
137. Tilley SD, Francis MB (2006) Tyrosine-selective protein alkylation using p-Allylpalladium complexes. J Am Chem Soc 128:1080-1081 (Pubitemid 43190612)
138. Antos JM, Francis MB (2006) Transition metal catalyzed methods for site-selective protein modification. Curr Opin Chem Biol 10:253-262 (Pubitemid 43815783)
139. Joshi NS, Whitaker LR, Francis MB (2004) A three-component Mannich-Type reaction for selective tyrosine bioconjugation. J Am Chem Soc 126:15942-15943 (Pubitemid 39627587)
140. Holder PG, Finley DT, Stephanopoulos N, Walton R, Clark DS, Francis MB (2010) Dramatic thermal stability of virus-polymer conjugates in hydrophobic solvents. Langmuir 26:17383-17388
141. Schlick TL, Ding Z, Kovacs EW, Francis MB (2005) Dual-surface modification of the tobacco mosaic virus. J Am Chem Soc 127:3718-3723 (Pubitemid 40411411)
142. Ban H, Gavrilyuk J, Barbas CF (2010) Tyrosine bioconjugation through aqueous ene-Type reactions: A click-like reaction for tyrosine. J Am Chem Soc 132:1523-1525
143. Tanaka T, Kamiya N, Nagamune T (2005) N-Terminal glycine-specific protein conjugation catalyzed by microbial transglutaminase. FEBS Lett 579:2092-2096 (Pubitemid 40469676)
144. FontanaA, SpolaoreB,MeroA,Veronese FM(2008) Site-specificmodification and PEGylation of pharmaceutical proteins mediated by transglutaminase. Adv Drug Deliv Rev 60:13-28 (Pubitemid 350181164)
145. Griffin M, Casadio R, Bergamini CM (2002) Transglutaminases: Nature's biological glues. Biochem J 368:377-396 (Pubitemid 35454517)
146. Yokoyama K, Nio N, Kikuchi Y (2004) Properties and applications of microbial transglutaminase. Appl Microbiol Biotechnol 64:447-454 (Pubitemid 38686152)
147. Mero A, Spolaore B, Veronese FM, Fontana A (2009) Transglutaminase- mediated PEGylation of proteins: Direct identification of the sites of protein modification by mass spectrometry using a novel monodisperse PEG. Bioconjugate Chem 20:384-389
148. Antos JM, Francis MB (2004) Selective tryptophan modification with rhodium carbenoids in aqueous solution. J Am Chem Soc 126:10256-10257 (Pubitemid 39100773)
149. Porath J (1992) Immobilized metal ion affinity chromatography. Protein Expr Purif 3:263-281
150. Smith MC, Furman TC, Ingolia TD, Pidgeon C (1988) Chelating peptide-immobilized metal ion affinity chromatography. A new concept in affinity chromatography for recombinant proteins. J Biol Chem 263:7211-7215
151. Kumar A, Kamihira M, Galaev IY, Iijima S, Mattiasson B (2003) Binding of Cu(II)-poly(Nisopropylacrylamide/ vinylimidazole) copolymer to histidine-Tagged protein: A surface plasmon resonance study surface plasmon resonance study. Langmuir 19:865-871
152. Griffith BR, Allen BL, Rapraeger AC, Kiessling LL (2004) A polymer scaffold for protein oligomerization. J Am Chem Soc 126:1608-1609 (Pubitemid 38222731)
153. Tahir MN, Natalio F, Berger R, Barz M, Theato P, Schröder H,Müller WE, TremelW(2009) Growth of fibrous aggregates of silica nanoparticles: Fibre growth by mimicking the biogenic silica patterning processes. Soft Matter 5:3657
154. Thompson LB, Mack NH (2010) Bifunctional polyacrylamide based polymers for the specific binding of hexahistidine tagged proteins on gold surfaces. Phys Chem Chem Phys 12:4301-4308
155. Shukoor MI, Natalio F, Therese HA, Tahir MN, Ksenofontov V, Panthöfer M, Eberhardt M, Theato P, Schröder HC, Müller WE, Tremel W (2008) Fabrication of a silica coating on magnetic g-Fe2O3 nanoparticles by an immobilized enzyme. Chem Mater 20:3567-3573
156. Shukoor M, Natalio F, Tahir M, Divekar M, Metz N, Therese H, Theato P, Ksenofontov V, Schröder H, Müller W, Tremel W (2008) Multifunctional polymer-derivatized g-Fe2O3
157. Zhang X, Li F, Lu X, Liu C (2009) Protein C-Terminal modification through thioacid/azide amidation. Bioconjugate Chem 20:197-200
158. Tam A, Soellner MB, Raines RT (2007) Water-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation. J Am Chem Soc 129:11421-11430 (Pubitemid 47555561)
159. Gao W, Liu W, Christensen T, Zalutsky MR, Chilkoti A (2010) In situ growth of a PEG-like polymer from the C terminus of an intein fusion protein improves pharmacokinetics and tumor accumulation. PNAS 107:16432-16437
160. Gauthier MA, Klok H (2011) Arginine-specific modification of proteins with polyethylene glycol. Biomacromolecules 12:482-493
161. de Graaf AJ, Kooijman M, Hennink WE, Mastrobattista E (2009) Nonnatural amino acids for site-specific protein conjugation. Bioconjugate Chem 20:1281-1295
162. Kochendoerfer GG, Chen S, Mao F, Cressman S, Traviglia S, Shao J, Hunter CL, Low DC, Carnevali M, Gueriguian V, Keogh P et al (2003) Design and chemical synthesis of a homogeneous polymer-modified erythropoiesis protein. Science 299:884-887 (Pubitemid 36182445)
163. Deiters A, Cropp TA, Summerer D, Mukherji M, Schultz PG (2004) Site-specific PEGylation of proteins containing unnatural amino acids. Bioorg Med Chem Lett 14:5743-5745 (Pubitemid 39421512)
164. Peeler JC, Woodman BF, Averick S, Miyake-Stoner SJ, Stokes AL, Hess KR, Matyjaszewski K, Mehl RA (2010) Genetically encoded initiator for polymer growth from proteins. J Am Chem Soc 132:13575-13577
165. Kempe K, Krieg A, Becer CR, Schubert US (2012) "Clicking" on/with polymers: A rapidly expanding field for the straightforward preparation of novel macromolecular architectures. Chem Soc Rev 41:176-191
166. Lallana E, Riguera R, Fernandez-Megia E (2011) Reliable and efficient procedures for the conjugation of biomolecules through Huisgen azide-Alkyne cycloadditions. Angew Chem Int Ed 50:8794-8804
167. Dirks AJ, van Berkel SS, Hatzakis NS, Opsteen JA, van Delft FL, Cornelissen JJ, Rowan AE, van Hest JC, Rutjes FP, Nolte RJ (2005) Preparation of biohybrid amphiphiles via the copper catalysed Huisgen [3+2] dipolar cycloaddition reaction. Chem Commun 4172-4174 (Pubitemid 41337171)
168. Li M, De P, Gondi SR, Sumerlin BS (2008) Responsive polymer-protein bioconjugates prepared by RAFT polymerization and copper-catalyzed azide-alkyne click chemistry. Macromol Rapid Commun 29:1172-1176
169. Shao H, Crnogorac MM, Kong T, Chen S, Williams JM, Tack JM, Gueriguian V, Cagle EN, Carnevali M, Tumelty D, Paliard X, Miranda LP, Bradburne JA, Kochendoerfer GG (2005) Site-specific polymer attachment to a CCL-5 (RANTES) analogue by oxime exchange. J Am Chem Soc 127:1350-1351 (Pubitemid 40204491)
170. Heredia KL, Tolstyka ZP, Maynard HD (2007) Aminooxy end-functionalized polymers synthesized by ATRP for chemoselective conjugation to proteins. Macromolecules 40:4772-4779 (Pubitemid 47169888)
171. Gao W, Liu W, Mackay JA, Zalutsky MR, Toone EJ, Chilkoti A (2009) In situ growth of a stoichiometric PEG-like conjugate at a protein's N-Terminus with significantly improved pharmacokinetics. PNAS 106:15231-15236