Electrostatic and Steric Effect of Peptides Functionalized on Self-Assembled Rosette Nanotubes


Discrete nanoscale tubular architectures have received significant attention during the past decade because of their potential role in electronic and photonic devices, sensors, liquid crystals, artificial channel systems and biomedical engineering [1-2]. Our research group has reported the synthesis and characterization of the bicyclic G∧C motif, a self complementary DNA base analogue, which undergoes hierarchical self-assembly to form Rosette Nanotubes (RNTs) [3]. The stability of this system depends however, on functional group density (sterics) and net charge (electrostatics) on the RNT surface [5c]. To this end, we have synthesized several G∧C modules bearing oligopeptides with different lengths and net charge and investigated their self-assembling properties.

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  1. 1.

    (a) S. J. Tans, M. H. Devoret, H. Dai, A. Thess, R. E. Smalley, L. J. Geerligs and C. Dekker, Nature, 386, 474 (1997); (b) D. T. Bong, T. D. Clark, J. R. Granja and M. R. Ghadiri. Angew. Chem., Int. Ed. 40, 988 (2001); (c) J. H. Jung, G. John, K. Yoshida, and T. Shimizu, J. Am. Chem. Soc. 124, 10674 (2002); (d) M. Reches and E. Gazit, Science, 300, 625 (2003); (e) R. J. Chen, C. H. Choi, S. Bangsaruntip, E. Yenilmez, W. Tang, Q. Wang, Y.-L. Chang and H. Dai, J. Am. Chem. Soc. 126, 1563 (2004); (f) D. Liu, S. H. Park, J. H. Reif and T. H. LaBean, Proc. Natl. Acad. Sci. U.S.A. 101, 717 (2004).

    CAS  Article  Google Scholar 

  2. 2.

    (a) J. G. Chun, H. Moralez, H. Fenniri and T. J. Webster, Nanotechnology, 15, S234 (2004); (b) A. L. Chun, J. Moralez, L. Zhang, S. Ramsaywack, H. Fenniri and T. Webster, J. Tissue Eng.: Part A, 14, 1353 (2008); (c) L. Zhang, F. Rakotondradany, A. J. Myles, H. Fenniri and T. Webster, J. Biomaterials, 30, 1309 (2009).

    CAS  Article  Google Scholar 

  3. 3.

    H. Fenniri, P. Mathivanan, K. L. Vidale, D. M. Sherman, K. Hallenga and K. V. Wood, J. Am. Chem. Soc. 123, 3854 (2001).

    CAS  Article  Google Scholar 

  4. 4.

    N. S. S. Kumar, S. Varghese, G. Narayan and S. Das, Angew. Chem. Int. Ed. 45, 6317 (2006).

    CAS  Article  Google Scholar 

  5. 5.

    (a) H. Fenniri, B.-L. Deng and A. E. Ribbe, J. Am. Chem. Soc. 124, 11064 (2002); (b) H. Fenniri, B.-L. Deng, A. E. Ribbe, K. Hallenga, J. Jacob and P. Thiyagarajan, Proc. Natl. Acad. Sci. U.S.A. 99, 6487 (2002); (c) J. G. Moralez, J. Raez, T. Yamazaki, M. R. Kishan, A. Kovalenko and H. Fenniri, J. Am. Chem. Soc. 127, 8307 (2005); (d) J. Raez, J. G. Moralez, and H. Fenniri, J. Am. Chem. Soc. 126, 16298 (2004).

    CAS  Article  Google Scholar 

  6. 6.

    Fmoc Solid Phase Peptide Synthesis: A Practical Approach; W. C. Chan ; P. D. White, Eds.; Oxford University Press: New York, (2000).

    Google Scholar 

  7. 7.

    The pka values of Kn.M and Kn.T was calculated using ChemAxon Ltd., physical properties software.

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Correspondence to Mounir El-Bakkari.

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El-Bakkari, M., Rachel, L.B., Alshamsan, A. et al. Electrostatic and Steric Effect of Peptides Functionalized on Self-Assembled Rosette Nanotubes. MRS Online Proceedings Library 1316, 1216 (2011). https://doi.org/10.1557/opl.2011.436

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