Inversion of Supramolecular Chirality by Sonication-Induced Organogelation

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Maity, Sibaprasad ^a   Das, Priyadip ^a   Reches, Meital ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84946893821     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep16365     Document Type: Article

References (61)

1. Baker, E. G. et al. Local and macroscopic electrostatic interactions in single alpha-helices. Nat. Chem. Biol. 11, 221-228 (2015).
2. Watson, J. D. & Crick, F. H. Molecular structure of nucleic acids; a structure for deoxyribose nucleic acid. Nature 171, 737-738 (1953).
3. Luo, Z. & Zhang, S. Designer nanomaterials using chiral self-assembling peptide systems and their emerging benefit for society. Chem. Soc. Rev. 41, 4736-4754 (2012).
4. Fletcher, J. M. et al. Self-assembling cages from coiled-coil peptide modules. Science (New York, N.Y.) 340, 595-599 (2013).
5. Thuong, N. T. & Hélène, C. Sequence-Specific Recognition and Modification of Double-Helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. in English 32, 666-690 (1993).
6. Pauling, L. & Corey, R. B. The structure of fibrous proteins of the collagen-gelatin group. Proc. Natl. Acad. Sci. USA. 37, 272-281 (1951).
7. Bhattacharjee, A. & Bansal, M. Collagen structure: The Madras triple helix and the current scenario. Iubmb Life 57, 161-172 (2005).
8. Tucker, A. R. Seashells of the World: a guide to the better-known species. Golden Press, New York (1985).
9. De Loos, M., Van Esch, J., Kellogg, R. M. & Feringa, B. L. Chiral Recognition in Bis-Urea-Based Aggregates and Organogels through Cooperative Interactions. Angew. Chem., Int. Ed. 113, 633-636 (2001).
10. Cornelissen, J. J. L. M., Rowan, A. E., Nolte, R. J. M. & Sommerdijk, N. A. J. M. Chiral Architectures from Macromolecular Building Blocks. Chem. Rev. 101, 4039-4070 (2001).
11. Rowan, A. E. & Nolte, R. J. M. Helical Molecular Programming. Angew. Chem., Int. Ed. 37, 63-68 (1998).
12. Schmuck, C. Molecules with Helical Structure: How To Build a Molecular Spiral Staircase. Angew. Chem., Int. Ed. 42, 2448-2452 (2003).
13. Würthner, F., Yao, S. & Beginn, U. Highly Ordered Merocyanine Dye Assemblies by Supramolecular Polymerization and Hierarchical Self-Organization. Angew. Chem., Int. Ed. 42, 3247-3250 (2003).
14. Guo, W. et al. Switchable Bifunctional Stimuli-Triggered Poly-N-Isopropylacrylamide/DNA Hydrogels. Angew. Chem., Int. Ed. 53, 10134-10138 (2014).
15. Kuhnle, A., Linderoth, T. R., Hammer, B. & Besenbacher, F. Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature 415, 891-893 (2002).
16. Thornton, P. D., Mart, R. J. & Ulijn, R. V. Enzyme-Responsive Polymer Hydrogel Particles for Controlled Release. Adv. Mater. 19, 1252-1256 (2007).
17. Kato, M., Sakai-Kato, K., Matsumoto, N. & Toyo'oka, T. A Protein-Encapsulation Technique by the Sol-Gel Method for the Preparation of Monolithic Columns for Capillary Electrochromatography. Anal. Chem. 74, 1915-1921 (2002).
18. Mohapatra, S. C. & Hsu, J. T. Optimizing lipase activity, enantioselectivity, and stability with medium engineering and immobilization for β -blocker synthesis. Biotechnol. Bioeng. 64, 213-220 (1999).
19. Ajayaghosh, A., Varghese, R., George, S. J. & Vijayakumar, C. Transcription and Amplification of Molecular Chirality to Oppositely Biased Supramolecular π Helices. Angew. Chem., Int. Ed. 45, 1141-1144 (2006).
20. Duan, P., Zhu, X. & Liu, M. Isomeric effect in the self-assembly of pyridine-containing L-glutamic lipid: substituent position controlled morphology and supramolecular chirality. Chem. Commun. 47, 5569-5571 (2011).
21. Prins, L. J., Huskens, J., de Jong, F., Timmerman, P. & Reinhoudt, D. N. Complete asymmetric induction of supramolecular chirality in a hydrogen-bonded assembly. Nature 398, 498-502 (1999).
22. Messmore, B. W., Sukerkar, P. A. & Stupp, S. I. Mirror Image Nanostructures. J. Am. Chem. Soc. 127, 7992-7993 (2005).
23. Duan, P., Cao, H., Zhang, L. & Liu, M. Gelation induced supramolecular chirality: chirality transfer, amplification and application. Soft Matter 10, 5428-5448 (2014).
24. Huang, X. et al. Self-Assembled Spiral Nanoarchitecture and Supramolecular Chirality in Langmuir-Blodgett Films of an Achiral Amphiphilic Barbituric Acid. J. Am. Chem. Soc. 126, 1322-1323 (2004).
25. Yuan, J. & Liu, M. Chiral Molecular Assemblies from a Novel Achiral Amphiphilic 2-(Heptadecyl) Naphtha[2,3]imidazole through Interfacial Coordination. J. Am. Chem. Soc. 125, 5051-5056 (2003).
26. Kumar, J., Tsumatori, H., Yuasa, J., Kawai, T. & Nakashima, T. Self-Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers. Angew. Chem., Int. Ed. 54, 5943-5947 (2015).
27. Wang, Q. et al. Morphology and chirality controlled self-assembled nanostructures of porphyrin-pentapeptide conjugate: effect of the peptide secondary conformation. J. Mater. Chem. 21, 8057-8065 (2011).
28. Hirst, A. R., Smith, D. K., Feiters, M. C. & Geurts, H. P. M. Two-Component Dendritic Gel: Effect of Stereochemistry on the Supramolecular Chiral Assembly. Chem. Eur. J. 10, 5901-5910 (2004).
29. Ahmed, S., Mondal, J. H., Behera, N. & Das, D. Self-Assembly of Peptide-Amphiphile Forming Helical Nanofibers and in Situ Template Synthesis of Uniform Mesoporous Single Wall Silica Nanotubes. Langmuir 29, 14274-14283 (2013).
30. Kurouski, D. et al. Levels of supramolecular chirality of polyglutamine aggregates revealed by vibrational circular dichroism. Febs Lett. 587, 1638-1643 (2013).
31. Conejero-Muriel, M. et al. Influence of the chirality of short peptide supramolecular hydrogels in protein crystallogenesis. Chem. Commun. 51, 3862-3865 (2015).
32. Rosen, B. M., Roche, C. & Percec, V. Self-assembly of dendritic dipeptides as a model of chiral selection in primitive biological systems. Top. Curr. Chem. 333, 213-253 (2013).
33. Liu, C., Jin, Q., Lv, K., Zhang, L. & Liu, M. Water tuned the helical nanostructures and supramolecular chirality in organogels. Chem. Commun. 50, 3702-3705 (2014).
34. Qing, G. et al. Solvent-driven chiral-interaction reversion for organogel formation. Angew. Chem., Int. Ed. 53, 2124-2129 (2014).
35. Insuasty, A., Atienza, C., Lópeza, J. L. & Martín, N. Supramolecular pentapeptide-based fullerene nanofibers: effect of molecular chirality. Chem. Commun. 51, 10506-10509 (2015).
36. Filler, R. & Saha, R. Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights. Future Med. Chem. 1, 777-791 (2009).
37. Maity, S., Nir, S., Zada, T. & Reches, M. Self-assembly of a tripeptide into a functional coating that resists fouling. Chem. Commun. 50, 11154-11157 (2014).
38. Ryan, D. M., Doran, T. M., Anderson, S. B. & Nilsson, B. L. Effect of C-Terminal Modification on the Self-Assembly and Hydrogelation of Fluorinated Fmoc-Phe Derivatives. Langmuir 27, 4029-4039 (2011).
39. Ryan, D. M., Doran, T. M. & Nilsson, B. L. Stabilizing self-assembled Fmoc-F5-Phe hydrogels by co-assembly with PEGfunctionalized monomers. Chem. Commun. 47, 475-477 (2011).
40. Liang, G. et al. Supramolecular Hydrogel of a d-Amino Acid Dipeptide for Controlled Drug Release in Vivo. Langmuir 25, 8419-8422 (2009).
41. Wu, F.-Y., Hsu, S.-M., Cheng, H., Hsu, L.-H. & Lin, H.-C. The effect of fluorine on supramolecular hydrogelation of 4-fluorobenzylcapped diphenylalanine. New J. Chem. 39, 4240-4243 (2015).
42. 3+ nanoclusters. Soft Matter 8, 7960-7966 (2012).
43. Bertolani, A. et al. Supramolecular amplification of amyloid self-assembly by iodination. Nat. Commun. doi: 10.1038/ncomms8574 (2015).
44. Dollendorf, C., Hetzer, M. & Ritter, H. Polymeric redox-responsive delivery systems bearing ammonium salts cross-linked via disulfides. Beilstein J. Org. Chem. 9, 1652-1662 (2013).
45. Khalily, M. A., Goktas, M. & Guler, M. O. Tuning viscoelastic properties of supramolecular peptide gels via dynamic covalent crosslinking. Org. Biomol. Chem. 13, 1983-1987 (2015).
46. Li, X. et al. Introducing d-Amino Acid or Simple Glycoside into Small Peptides to Enable Supramolecular Hydrogelators to Resist Proteolysis. Langmuir 28, 13512-13517 (2012).
47. Maity, S., Kumar, P. & Haldar, D. Sonication-induced instant amyloid-like fibril formation and organogelation by a tripeptide. Soft Matter 7, 5239-5245 (2011).
48. Wang, R. et al. Trifluoromethylated nucleic acid analogues capable of self-assembly through hydrophobic interactions. Chem. Sci. 5, 4076-4081 (2014).
49. Kong, J. & Yu, S. Fourier transform infrared spectroscopic analysis of protein secondary structures. Acta Biochim Biophys. 39, 549-559 (2007).
50. Reches, M. & Gazit, E. Controlled patterning of aligned self-assembled peptide nanotubes. Nat. Nanotechnol. 1, 195-200 (2006).
51. Adochitei, A. & Drochioiu, G. Rapid characterization of peptide secoendary structure by FT-IR spectroscopy. Rev. Roum. Chim. 56, 783-791 (2011).
52. Yuran, S., Razvag, Y. & Reches, M. Coassembly of Aromatic Dipeptides into Biomolecular Necklaces. Acs Nano 6, 9559-9566 (2012).
53. Baker, R. J., Colavita, P. E., Murphy, D. M., Platts, J. A. & Wallis, J. D. Fluorine-Fluorine Interactions in the Solid State: An Experimental and Theoretical Study. J. Phys. Chem. A 116, 1435-1444 (2012).
54. Gupta, M. et al. Self-Assembly of a Dipeptide-Containing Conformationally Restricted Dehydrophenylalanine Residue to Form Ordered Nanotubes. Adv. Mater. 19, 858-861 (2007).
55. Tinker, D. A., Krebs, E. A., Feltham, I. C. & Attahpoku, S. K. & Ananthanarayanan. Synthetic Beta-Turn Peptides as Substrates for a Tyrosine Protein-Kinase. J. Biol. Chem. 263, 5024-5026 (1988).
56. Afrasiabi, R. & Kraatz, H.-B. Sonication-Induced Coiled Fibrous Architectures of Boc-L-Phe-L-Lys(Z)-OMe. Chem. Eur. J. 19, 1769-1777 (2013).
57. Muraoka, T., Cui, H. & Stupp, S. I. Quadruple Helix Formation of a Photoresponsive Peptide Amphiphile and Its Light-Triggered Dissociation into Single Fibers. J. Am. Chem. Soc. 130, 2946-2947 (2008).
58. Kumar, J., Nakashima, T. & Kawai, T. Inversion of Supramolecular Chirality in Bichromophoric Perylene Bisimides: Influence of Temperature and Ultrasound. Langmuir 30, 6030-6037 (2014).
59. Adhikari, B., Nanda, J. & Banerjee, A. Multicomponent hydrogels from enantiomeric amino acid derivatives: helical nanofibers, handedness and self-sorting. Soft Matter 7, 8913-8922 (2011).
60. Reches, M. & Gazit, E. Casting Metal Nanowires within Discrete Self-Assembled Peptide Nanotubes. Science 300, 625-627 (2003).
61. Reches, M. & Gazit, E. Designed Aromatic Homo-Dipeptides: Foramtion of Ordered Nanostructures and Potential Nanotechnological Applications. Phys. Biol. 3, S10-S19 (2006).