Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Synthesis of Self-assembling Cyclic Peptide-polymer Conjugates using Click Chemistry

Robert Chapman A B , Katrina A. Jolliffe A and Sébastien Perrier A

A Key Centre for Polymers & Colloids, School of Chemistry, The University of Sydney, NSW 2006, Australia.

B Corresponding author. Email:

Australian Journal of Chemistry 63(8) 1169-1172
Submitted: 18 March 2010  Accepted: 30 June 2010   Published: 10 August 2010


Self-assembling cyclic peptide-polymer conjugates were prepared by ‘clicking’ polymers (prepared by RAFT polymerization) to an azide functionalized d-alt-l cyclic octapeptide via the Huisgen 1,3-dipolar cycloaddition reaction. Due to the high graft density, the efficiency of the click chemistry conjugation reaction was found to be highly dependent on the size of the polymer. At relatively low molecular weights, as many as four polymer chains could be grafted to each 8 residue cyclic peptide ring. Evidence for the self assembly of the conjugates into peptide-polymer nanotubes was observed by TEM and IR.


[1]  Hawker C. J.Wooley K. L.2005Science3091200doi:10.1126/SCIENCE.1109778

[2]  Ariga K.Hill J. P.Lee M. V.Vinu A.Charvet R.Acharya S.2008Sci. Technol. Adv. Mater.9014109doi:10.1088/1468-6996/9/1/014109

[3]  Scanlon S.Aggeli A.2008Nano Today322doi:10.1016/S1748-0132(08)70041-0

[4]  Hamley I. W.2007Angew. Chem. Int. Ed.468128doi:10.1002/ANIE.200700861

[5]  König H. M.Kilbinger A. F. M.2007Angew. Chem. Int. Ed.468334doi:10.1002/ANIE.200701167

[6]  Bong D. T.Clark T. D.Granja J. R.Ghadiri M. R.2001Angew. Chem. Int. Ed.40988doi:10.1002/1521-3773(20010316)40:6<988::AID-ANIE9880>3.0.CO;2-N

[7]  Boyer C.Bulmus V.Davis T. P.Ladmiral V.Liu J.Perrier S.2009Chem. Rev.1095402doi:10.1021/CR9001403

[8]  Börner H. G.2009Prog. Polym. Sci.34811doi:10.1016/J.PROGPOLYMSCI.2009.05.001

[9]  Klok H. A.2009Macromolecules427990doi:10.1021/MA901561T

[10]  Van Hest J. C. M.2007Pol. Rev.4763doi:10.1080/15583720601109578

[11]  Zhao Y. L.Perrier S.2007Chem. Commun.4294doi:10.1039/B708293B

[12]  Couet J.Jeyaprakash J. D.Samuel S.Kopyshev A.Santer S.Biesalski M.2005Angew. Chem. Int. Ed.443297doi:10.1002/ANIE.200462993

[13]  Loschonsky S.Couet J.Biesalski M.2008Macromol. Rapid Commun.29309doi:10.1002/MARC.200700700

[14]  Couet J.Biesalski M.2006Macromolecules397258doi:10.1021/MA061200J

[15]  Couet J.Biesalski M.2008Small41008doi:10.1002/SMLL.200700967

[16]  Kakwere H.Chun K. Y.Jolliffe K. A.Payne R. J.Perrier S.2010Chem. Commun.462188doi:10.1039/B924112D

[17]  ten Cate M. G. J.Severin N.Börner H. G.2006Macromolecules397831doi:10.1021/MA061738P

[18]  Abbreviations: 1-hydroxy-l-azabenzotriazoleuronium (HBTU), O-benzotriazole-l-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HOBt), triisopropylsilane (Trends Pharmacol. Sci.).

[19]  Goddard-Borger E. D.Stick R. V.2007Org. Lett.93797doi:10.1021/OL701581G

[20]  Perrier S.Takolpuckdee P.2005J. Polym. Sci. Part Polym. Chem.435347doi:10.1002/POLA.20986

[21]  Moad G.Rizzardo E.Thang S. H.2006Aust. J. Chem.59669doi:10.1071/CH06250

[22]  Legge T. M.Slark A. T.Perrier S.2006J. Polym. Sci. Part Polym. Chem.446980doi:10.1002/POLA.21803

[23]  Dirks A. J. T.van Berkel S. S.Hatzakis N. S.Opsteen J. A.van Delft F. L.Cornelissen J.Rowan A. E.van Hest J. C. M.Rutjes F.Nolte R. J. M.2005Chem. Commun.4172doi:10.1039/B508428H

[24]  Vogt A. P.Gondi S. R.Sumerlin B. S.2007Aust. J. Chem.60396doi:10.1071/CH07077

[25]  Ghadiri M. R.Granja J. R.Milligan R. A.McRee D. E.Khazanovich N.1993Nature366324doi:10.1038/366324A0

[26]  Ghadiri M. R.Granja J. R.Buehler L. K.1994Nature369301doi:10.1038/369301A0

Supplementary MaterialSupplementary Material (66 KB) Export Citation