Skip to main content

Part of the book series: Advances in Polymer Science ((POLYMER,volume 262))

Abstract

Life as we know it is impossible without formation of hierarchical structures. First and foremost, proteins, that is, sequence-specific polypeptides, are nature′s vanguard in this respect. Peptoids and polypeptoids are structural isomers and analogs to peptides and polypeptides. Here, we review the advancements over the last few years on biomimetic hierarchical structures obtained using polypeptoids. Although the inherently more flexible amide bond in peptoids make the stabilization of secondary structure challenging, it also gives us a tool to direct the conformation of the amide bond by design. As will be seen, this is a particularly important feature of peptoids.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Pauling L, Corey RB (1950) J Am Chem Soc 72:5349

    CAS  Google Scholar 

  2. Pauling L, Corey RB, Branson HR (1951) Proc Natl Acad Sci USA 37:205

    CAS  Google Scholar 

  3. Merrifield RB (1963) J Am Chem Soc 85:2149

    CAS  Google Scholar 

  4. Taylor DJ, Krishna NK, Canady MA, Schneemann A, Johnson JE (2002) J Virol 76:9972

    CAS  Google Scholar 

  5. Bram S, Butler-Browne G, Baudy P, Ibel K (1975) Proc Natl Acad Sci USA 72:1043

    CAS  Google Scholar 

  6. Han D, Pal S, Nangreave J, Deng Z, Liu Y, Yan H (2011) Science 332:342

    CAS  Google Scholar 

  7. Chiti F, Dobson CM (2006) Annu Rev Biochem 75:333

    CAS  Google Scholar 

  8. Gething M-J, Sambrook J (1992) Nature 355:33

    CAS  Google Scholar 

  9. Dobson CM (2003) Nature 426:884

    CAS  Google Scholar 

  10. Plaxco KW, Simons KT, Baker D (1998) J Polym Sci Pol Phys 277:985

    CAS  Google Scholar 

  11. Makarov E (2003) Protein Sci 12:17

    CAS  Google Scholar 

  12. Fowler SA, Blackwell HE (2009) Org Biomol Chem 7:1508

    CAS  Google Scholar 

  13. Sun J, Zuckermann RN (2013) ACS Nano 7(6):4715–4732

    Google Scholar 

  14. Luxenhofer R, Fetsch C, Grossmann A (2013) J Polym Sci Polym Chem 51:2731

    CAS  Google Scholar 

  15. Zuckermann RN (2011) Biopolymers 96:545

    CAS  Google Scholar 

  16. Wetzler M, Barron AE (2011) Biopolymers 96:556

    CAS  Google Scholar 

  17. Walsh CT, Garneau-Tsodikova S, Gatto GJ (2005) Angew Chem Int Ed 44:7342

    CAS  Google Scholar 

  18. Yokoyama M, Inoue S, Kataoka K, Yui N, Sakurai Y (1987) Makromol Chem Rapid 8:431

    CAS  Google Scholar 

  19. Luxenhofer R, Jordan R (2006) Macromolecules 39:3509

    CAS  Google Scholar 

  20. Stepto RFT (2010) Polym Int 59:23

    CAS  Google Scholar 

  21. Mio MJ, Prince RB, Moore JS, Kuebel C, Martin DC (2000) J Am Chem Soc 122:6134

    CAS  Google Scholar 

  22. Hartmann L, Börner HG (2009) Adv Mater 21:3425

    CAS  Google Scholar 

  23. Simon RJ, Kania RS, Zuckermann RN, Huebner VD, Jewell DA, Banville S, Ng S, Wang L, Rosenberg S, Marlowe CK, Spellmeyer DC, Tan R, Frankel AD, Santi DV, Cohen FE, Bartlett PA (1992) Proc Natl Acad Sci USA 89:9367

    CAS  Google Scholar 

  24. Yoo B, Kirshenbaum K (2008) Curr Opin Chem Biol 12:714

    CAS  Google Scholar 

  25. Stringer JR, Crapster JA, Guzei IA, Blackwell HE (2010) J Org Chem 75:6068

    CAS  Google Scholar 

  26. Shah NH, Kirshenbaum K (2008) Org Biomol Chem 6:2516

    CAS  Google Scholar 

  27. Kapoor R, Eimerman PR, Hardy JW, Cirillo JD, Contag CH, Barron AE (2011) Antimicrob Agents Chemother 55:3058

    CAS  Google Scholar 

  28. Rosales AM, Murnen HK, Zuckermann RN, Segalman RA (2010) Macromolecules 43:5627

    CAS  Google Scholar 

  29. Sigmund F, Wessely F (1926) H-S Z Physiol Chem 157:91

    Google Scholar 

  30. Kricheldorf HR (2006) Angew Chem Int Ed 45:5752

    CAS  Google Scholar 

  31. Staudinger H (1920) Chem Ber 53:1073

    Google Scholar 

  32. Waley SG, Watson J (1949) P Roy Soc Lond A Mat 199:499

    CAS  Google Scholar 

  33. Szwarc M (1956) Nature 178:1168

    CAS  Google Scholar 

  34. Sisido M, Imanishi Y, Higashimura T (1977) Makromol Chem 178:3107

    CAS  Google Scholar 

  35. Kricheldorf HR (1987) α-Aminoacid-N-carboxyanhydrides and related materials. Springer, New York

    Google Scholar 

  36. Kidchob T, Kimura S, Imanishi Y (1996) J Contr Release 40:285

    CAS  Google Scholar 

  37. Kidchob T, Kimura S, Imanishi Y (1997) J Appl Polym Sci 63:453

    CAS  Google Scholar 

  38. Kidchob T, Kimura S, Imanishi Y (1998) J Contr Release 50:205

    CAS  Google Scholar 

  39. Aoi K, Hatanaka T, Tsutsumiuchi K, Okada M, Imae T (1999) Macromol Rapid Commun 20:378

    CAS  Google Scholar 

  40. Aoi K, Nakamura R, Okada M (2000) Macromol Chem Phys 201:1059

    CAS  Google Scholar 

  41. Guo L, Zhang D (2009) J Am Chem Soc 131:18072

    CAS  Google Scholar 

  42. Zhang D, Lahasky SH, Guo L, Lee C-U, Lavan M (2012) Macromolecules 45:5833

    CAS  Google Scholar 

  43. Lahasky SH, Serem WK, Guo L, Garno JC, Zhang D (2011) Macromolecules 44:9063

    CAS  Google Scholar 

  44. Robinson JW, Schlaad H (2012) Chem Commun 48:7835

    CAS  Google Scholar 

  45. Fetsch C, Grossmann A, Holz L, Nawroth JF, Luxenhofer R (2011) Macromolecules 44:6746

    CAS  Google Scholar 

  46. Fetsch C, Luxenhofer R (2013) Polymers 5:112

    Google Scholar 

  47. Guo L, Li J, Brown Z, Ghale K, Zhang D (2011) Biopolymers 96:596

    CAS  Google Scholar 

  48. Lahasky SH, Hu X, Zhang D (2012) ACS Macro Lett 1:580

    CAS  Google Scholar 

  49. Robinson JW, Secker C, Weidner S, Schlaad H (2013) Macromolecules 46:580

    CAS  Google Scholar 

  50. Fetsch C, Luxenhofer R (2012) Macromol Rapid Commun 33:1708

    CAS  Google Scholar 

  51. Schneider M, Fetsch C, Amin I, Jordan R, Luxenhofer R (2013) Langmuir 29:6983

    CAS  Google Scholar 

  52. Gangloff N, Fetsch C, Luxenhofer R (2013) Macromol Rapid Commun 34:997

    CAS  Google Scholar 

  53. Armand P, Kirshenbaum K, Falicov A, Dunbrack RL, Dill KA, Zuckermann RN, Cohen FE (1997) Fold Des 2:369

    CAS  Google Scholar 

  54. Armand P, Kirshenbaum K, Goldsmith RA, Farr-Jones S, Barron AE, Truong KT, Dill KA, Mierke DF, Cohen FE, Zuckermann RN, Bradley EK (1998) Proc Natl Acad Sci USA 95:4309

    CAS  Google Scholar 

  55. Gorske BC, Stringer JR, Bastian BL, Fowler SA, Blackwell HE (2009) J Am Chem Soc 131:16555

    CAS  Google Scholar 

  56. Shah NH, Butterfoss GL, Nguyen K, Yoo B, Bonneau R, Rabenstein DL, Kirshenbaum K (2008) J Am Chem Soc 130:16622

    CAS  Google Scholar 

  57. Jordan PA, Paul B, Butterfoss GL, Renfrew PD, Bonneau R, Kirshenbaum K (2011) Biopolymers 96:617

    CAS  Google Scholar 

  58. Crapster JA, Stringer JR, Guzei IA, Blackwell HE (2011) Biopolymers 96:604

    CAS  Google Scholar 

  59. Kirshenbaum K, Barron AE, Goldsmith RA, Armand P, Bradley EK, Truong KT, Dill KA, Cohen FE, Zuckermann RN (1998) Proc Natl Acad Sci USA 95:4303

    CAS  Google Scholar 

  60. Wu CW, Sanborn TJ, Zuckermann RN, Barron AE (2001) J Am Chem Soc 123:2958

    CAS  Google Scholar 

  61. Wu CW, Sanborn TJ, Huang K, Zuckermann RN, Barron AE (2001) J Am Chem Soc 123:6778

    CAS  Google Scholar 

  62. Wu CW, Kirshenbaum K, Sanborn TJ, Patch JA, Huang K, Dill KA, Zuckermann RN, Barron AE (2003) J Am Chem Soc 125:13525

    CAS  Google Scholar 

  63. Fasman GD, Blout ER (1963) Biopolymers 1:99

    CAS  Google Scholar 

  64. Luxenhofer R, Huber S, Hytry J, Tong J, Kabanov AV, Jordan R (2013) J Polym Sci Polym Chem 51:732

    CAS  Google Scholar 

  65. Sanborn TJ, Wu CW, Zuckermann RN, Barron AE (2002) Biopolymers 63:12

    CAS  Google Scholar 

  66. Doose S, Neuweiler H, Barsch H, Sauer M (2007) Proc Natl Acad Sci USA 104:17400

    CAS  Google Scholar 

  67. Best RB, Merchant KA, Gopich IV, Schuler B, Bax A, Eaton WA (2007) Proc Natl Acad Sci USA 104:18964

    CAS  Google Scholar 

  68. Rosales AM, Murnen HK, Kline SR, Zuckermann RN, Segalman RA (2012) Soft Matter 8:3673

    CAS  Google Scholar 

  69. Stringer JR, Crapster JA, Guzei IA, Blackwell HE (2011) J Am Chem Soc 133:15559

    CAS  Google Scholar 

  70. Holub JM, Jang H, Kirshenbaum K (2007) Org Lett 9:3275

    CAS  Google Scholar 

  71. Vaz B, Brunsveld L (2008) Org Biomol Chem 6:2988

    CAS  Google Scholar 

  72. Seo J, Barron AE, Zuckermann RN (2010) Org Lett 12:492

    CAS  Google Scholar 

  73. Kümin M, Sonntag L-S, Wennemers H (2006) J Am Chem Soc 129:466

    Google Scholar 

  74. Yu YB (2002) Adv Drug Deliv Rev 54:1113

    CAS  Google Scholar 

  75. Lupas AN, Gruber M (2005) Adv Protein Chem 70:37

    CAS  Google Scholar 

  76. Xu T, Shu J (2009) Soft Matter 6:212

    Google Scholar 

  77. Sternberg U, Birtalan E, Jakovkin I, Luy B, Schepers U, Bräse S, Muhle-Goll C (2013) Org Biomol Chem 11:640

    CAS  Google Scholar 

  78. Kang B, Chung S, Ahn YD, Lee J, Seo J (2013) Org Lett 15:1670

    CAS  Google Scholar 

  79. Leszczynski JF, Rose GD (1986) Science 234:849

    CAS  Google Scholar 

  80. Fiser A, Do RKG, Sali A (2000) Protein Sci 9:1753

    CAS  Google Scholar 

  81. Shehu A, Kavraki LE (2012) Entropy 14:252

    CAS  Google Scholar 

  82. Wheatley M, Wootten D, Conner T, Simms J, Kendrick R, Logan T, Poyner R, Barwell J (2012) Br J Pharmacol 165:1688

    CAS  Google Scholar 

  83. Huang K, Wu CW, Sanborn TJ, Patch JA, Kirshenbaum K, Zuckermann RN, Barron AE, Radhakrishnan I (2006) J Am Chem Soc 128:1733

    CAS  Google Scholar 

  84. Gorske BC, Blackwell HE (2006) J Am Chem Soc 128:14378

    CAS  Google Scholar 

  85. Fowler SA, Luechapanichkul R, Blackwell HE (2009) J Org Chem 74:1440

    CAS  Google Scholar 

  86. Pokorski JK, Miller Jenkins LM, Feng H, Durell SR, Bai Y, Appella DH (2007) Org Lett 9:2381

    CAS  Google Scholar 

  87. Crapster JA, Guzei IA, Blackwell HE (2013) Angew Chem Int Ed 52:5079

    CAS  Google Scholar 

  88. Karle IL, Flippen-Anderson J, Sukumar M, Balaram P (1987) Proc Natl Acad Sci USA 84:5087

    CAS  Google Scholar 

  89. Butterfoss GL, Yoo B, Jaworski JN, Chorny I, Dill KA, Zuckermann RN, Bonneau R, Kirshenbaum K, Voelz VA (2012) Proc Natl Acad Sci USA 109:14320

    CAS  Google Scholar 

  90. Maayan G, Ward MD, Kirshenbaum K (2009) Proc Natl Acad Sci USA 106:13679

    CAS  Google Scholar 

  91. Newkome GR, Moorefield CN, Baker GR, Saunders MJ, Grossman SH (1991) Angew Chem Int Ed 30:1178

    Google Scholar 

  92. Kurniasih IN, Liang H, Kumar S, Mohr A, Sharma SK, Rabe JP, Haag R (2013) J Mat Chem B 1(29):3569-3577 doi:10.1039/c3tb20366b

    Google Scholar 

  93. Murnen HK, Khokhlov AR, Khalatur PG, Segalman RA, Zuckermann RN (2012) Macromolecules 45:5229

    CAS  Google Scholar 

  94. Wiggins PM (1997) Physica A 238:113

    CAS  Google Scholar 

  95. Arai M, Kuwajima K (2000) Adv Protein Chem 53:209

    CAS  Google Scholar 

  96. Hecht MH, Das A, Go A, Bradley LH, Wei Y (2004) Protein Sci 13:1711

    CAS  Google Scholar 

  97. Zarrine-Afsar A, Wallin S, Neculai AM, Neudecker P, Howell PL, Davidson AR, Chan HS (2008) Proc Natl Acad Sci USA 105:9999

    CAS  Google Scholar 

  98. Dill KA, Ozkan SB, Shell MS, Weikl TR (2008) Annu Rev Biophys 37:289

    CAS  Google Scholar 

  99. Barz M, Luxenhofer R, Zentel R, Kabanov AV (2009) Biomaterials 30:5682

    CAS  Google Scholar 

  100. Hemmelmann M, Metz VV, Koynov K, Blank K, Postina R, Zentel R (2012) J Contr Release 163:170

    CAS  Google Scholar 

  101. Burkoth TS, Beausoleil E, Kaur S, Tang D, Cohen FE, Zuckermann RN (2002) Chem Biol 9:647

    CAS  Google Scholar 

  102. Lee B-C, Zuckermann RN, Dill KA (2005) J Am Chem Soc 127:10999

    CAS  Google Scholar 

  103. Theodore Gillman MH (1958) Brit Med J 2:635

    Google Scholar 

  104. Coleman JE (1992) Annu Rev Biochem 61:897

    CAS  Google Scholar 

  105. McCall KA, Huang C-C, Fierke CA (2000) J Nutr 130:1437S

    CAS  Google Scholar 

  106. Blasie CA, Berg JM (2002) Biochemistry 41:15068

    CAS  Google Scholar 

  107. Magyar JS, Weng T-C, Stern CM, Dye DF, Rous BW, Payne JC, Bridgewater BM, Mijovilovich A, Parkin G, Zaleski JM (2005) J Am Chem Soc 127:9495

    CAS  Google Scholar 

  108. Lee B-C, Chu TK, Dill KA, Zuckermann RN (2008) J Am Chem Soc 130:8847

    CAS  Google Scholar 

  109. Nam KT, Shelby SA, Choi PH, Marciel AB, Chen R, Tan L, Chu TK, Mesch RA, Lee BC, Connolly MD, Kisielowski C, Zuckermann RN (2010) Nat Mater 9:454

    CAS  Google Scholar 

  110. Sanii B, Kudirka R, Cho A, Venkateswaran N, Olivier GK, Olson AM, Tran H, Harada RM, Tan L, Zuckermann RN (2011) J Am Chem Soc 133:20808

    CAS  Google Scholar 

  111. Kudirka R, Tran H, Sanii B, Nam KT, Choi PH, Venkateswaran N, Chen R, Whitelam S, Zuckermann RN (2011) Biopolymers 96:586

    CAS  Google Scholar 

  112. Murnen HK, Rosales AM, Jaworski JN, Segalman RA, Zuckermann RN (2010) J Am Chem Soc 132:16112

    CAS  Google Scholar 

  113. Kanzaki T, Horikawa Y, Makino A, Sugiyama J, Kimura S (2008) Macromol Biosci 8:1026

    CAS  Google Scholar 

  114. Jain S, Bates FS (2003) Science 300:460

    CAS  Google Scholar 

  115. Ueda M, Makino A, Imai T, Sugiyama J, Kimura S (2011) Chem Commun 47:3204

    CAS  Google Scholar 

  116. Ueda M, Makino A, Imai T, Sugiyama J, Kimura S (2011) J Pept Sci 17:94

    CAS  Google Scholar 

  117. Lee CU, Smart TP, Guo L, Epps TH, Zhang D (2011) Macromolecules 44:9574

    CAS  Google Scholar 

Download references

Acknowledgement

We gratefully acknowledge financial support from the German Plastics Center SKZ and the Universität Würzburg for start-up funding.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Robert Luxenhofer .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Gangloff, N., Luxenhofer, R. (2013). Peptoids for Biomimetic Hierarchical Structures. In: Percec, V. (eds) Hierarchical Macromolecular Structures: 60 Years after the Staudinger Nobel Prize II. Advances in Polymer Science, vol 262. Springer, Cham. https://doi.org/10.1007/12_2013_237

Download citation

Publish with us

Policies and ethics