Ranking the affinity of aromatic residues for carbon nanotubes by using designed surfactant peptides

Journal of Peptide Science

Volumn 14, Issue 2, 2008, Pages 139-151

  Xie, Hui ^a   Becraft, Eric J ^a   Baughman, Ray H ^a   Dalton, Alan B ^b   Dieckmann, Gregg R ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

^b UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Aromatic residue; Carbon nanotube; Dispersion; Nanotechnology; Protein design; Raman spectroscopy; Sedimentation equilibrium ultracentrifugation; Surfactant

Indexed keywords

AROMATIC AMINO ACID; CARBON NANOTUBE; LYSINE; PEPTIDE DERIVATIVE; PHENYLALANINE; SURFACTANT; TRYPTOPHAN; VALINE;

AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DISPERSION; HYDROPHILICITY; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN FOLDING; PROTEIN INTERACTION; PROTEIN STRUCTURE; RAMAN SPECTROMETRY; RESIDUE ANALYSIS; SEDIMENTATION; ULTRACENTRIFUGATION;

CIRCULAR DICHROISM; MICROSCOPY, ELECTRON, SCANNING; MODELS, MOLECULAR; NANOTUBES, CARBON; PEPTIDES; PROTEIN STRUCTURE, TERTIARY; SOLUTIONS; SPECTRUM ANALYSIS, RAMAN; SURFACE-ACTIVE AGENTS;

EID: 39649097181     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.978     Document Type: Article

References (67)

1. Dresselhaus MS, Dresselhaus G, Avouris P (eds). Carbon Nanotubes: Synthesis, Structure, Properties, and Applications, Vol. 80. Springer: New York, 2001.
2. Bahr JL, Mickelson ET, Bronikowski MJ, Smalley RE, Tour JM. Dissolution of small diameter single-wall carbon nanotubes in organic solvents? Chem. Commun. 2001; 193-194.
3. Niyogi S, Hamon MA, Hu H, Zhao B, Bhowmik P, Sen R, Itkis ME, Haddon RC. Chemistry of single-walled carbon nanotubes. Acc. Chem. Res. 2002; 35: 1105-1113.
4. Sinnott SB. Chemical functionalization of carbon nanotubes. J. Nanosci. Nanotechnol. 2002; 2: 113-123.
5. Sun Y-P, Fu K, Lin Y, Huang W. Functionalized carbon nanotubes: properties and applications. Acc. Chem. Res. 2002; 35: 1096-1104.
6. Bahr JL, Tour JM. Covalent chemistry of single-wall carbon nanotubes. J. Mater. Chem. 2002; 12: 1952-1958.
7. Hirsch A. Functionalization of single-walled carbon nanotubes. Angew. Chem. Int. Ed. Engl. 2002; 41: 1853-1859.
8. Boul PJ, Liu J, Mickelson ET, Huffman CB, Ericson LM, Chiang IW, Smith KA, Colbert DT, Hauge RH, Magrave JL, Smalley RE. Reversible sidewall functionalization of buckytubes. Chem. Phys. Lett. 1999; 310: 367-372.
9. Chen J, Hamon MA, Hu H, Chen Y, Rao AM, Eklund PC, Haddon RC. Solution properties of single-walled carbon nanotubes. Science 1998; 282: 95-98.
10. Vigolo B, Penicaud A, Coulon C, Sauder C, Pailler R, Journet C, Bernier P, Poulin P, Macroscopic fibers and ribbons of oriented carbon nanotubes. Science 2000; 290: 1331-1334.
11. O'Connell MJ, Bachilo SM, Huffman CB, Moore VC, Strano MS, Haroz EH, Rialon KL, Boul PJ, Noon WH, Kittren C, Ma JP, Hauge RH, Weisman RB, Smalley RE. Band gap fluorescence from individual single-walled carbon nanotubes. Science 2002; 297: 593 -596.
12. O'Connell MJ, Boul P, Ericson LM, Huffman C, Wang Y, Haroz E, Kuper C, Tour J, Ausman KD, Smalley RE. Reversible water-solubilization of single-walled carbon nanotubes by polymer wrapping. Chem. Phys. Lett. 2001; 342: 265-271.
13. Curran SA, Ajayan PM, Blau WJ, Carroll DL, Coleman JN, Dalton AB, Davey AP, Drury A, McCarthy B, Maier S, Strevens A. A composite from poly(m-phenylenevinylene-co-2,5-dioctoxy-p-phenylenevinylene) and carbon nanotubes: A novel material for molecular optoelectronics. Adv. Mater. 1998; 10: 1091-1094.
14. Tang BZ, Xu HY. Preparation, alignment, and optical properties of soluble poly(phenylacetylene)-wrapped carbon nanotubes. Macromolecules 1999; 32: 2569-2576.
15. Zheng M, Jagota A, Strano MS, Santos AP, Barone P, Chou SG, Diner BA, Dresselhaus MS, Mclean RS, Onoa GB, Samsonidze GG, Semke ED, Usrey ML, Walls DJ. Structure-based carbon nanotube sorting by sequence-dependent DNA assembly. Science 2003; 302: 1545-1548.
16. Zheng M, Jagota A, Semke ED, Diner BA, Mclean RS, Lustig SR, Richardson RE, Tassi NG. DNA-assisted dispersion and separation of carbon nanotubes. Nat. Mater 2003; 2: 338-342.
17. Arnold MS, Guler MO, Hersam MC, Stupp SI. Encapsulation of carbon nanotubes by self-assembling peptide amphiphiles. Langmuir 2005; 21: 4705-4709.
18. Witus LS, Rocha J-DR, Yuwono VM, Paramonov SE, Weisman RB, Hartgerink JD. Peptides that non-covalently functionalize single-walled carbon nanotubes to give controlled solubility characteristics. J. Math. Chem. 2007; 17: 1909-1915.
19. Dieckmann GR, Dalton AB, Johnson PA, Razal J, Chen J, Giordano GM, Munoz E, Musselman IH, Baughman RH, Draper RK. Controlled assembly of carbon nanotubes by designed amphiphilic peptide helices. J. Am. Chem. Soc. 2003; 125: 1770-1777.
20. Zorbas V, Ortiz-Acevedo A, Dalton AB, Yoshida MM, Dieckmann GR, Draper RK, Baughman RH, Jose-Yacaman M, Musselman IH. Preparation and characterization of individual peptide-wrapped single-walled carbon nanotubes. J. Am. Chem. Soc. 2004; 126: 7222-7227.
21. Dalton AB, Ortiz-Acevedo A, Zorbas V, Brunner E, Sampson WM, Collins S, Razal JM, Yoshida MM, Baughman RH, Draper RK, Musselman IH, Jose-Yacaman M, Dieckmann GR. Hierarchical Self-assembly of peptide-coated carbon nanotubes. Adv. Funct. Mater. 2004; 14:1147-1151.
22. Xie H, Ortiz-Acevedo A, Baughman RH, Draper RK, Musselman IH, Dalton AB, Dieckmann GR. Peptide cross-linking modulated stability and assembly of peptide-wrapped single-walled carbon nanotubes. J. Mater. Chem. 2005; 15: 1734-1741.
23. Zorbas V, Smith AL, Ortiz-Acevedo A, Xie H, Dalton AB, Dieckmann GR, Draper RK, Baughman RH, Musselman IH. Importance of aromatic content for peptides/single-walled carbon nanotube interactions. J. Am. Chem. Soc. 2005; 127: 12323-12328.
24. Mclachlan AD, Stewart M. Tropomyosin Coiled-Coil Interactions-evidence for an Unstaggered structure. J. Mol. Biol. 1975; 98: 293-304.
25. Islam MF, Rojas E, Bergey DM, Johnson AT, Yodh AG. High weight fraction surfactant solubilization of single-wall carbon nanotubes in water. Nano Lett. 2003; 3: 269-273.
26. Chen RJ, Zhang Y, Wang D, Dai H. Noncovalent sidewall functionalization of single-walled carbon nanotubes for protein immobilization. J. Am. Chem. Soc. 2001; 123: 3838-3839.
27. Oakley MG, Hollenbeck JJ. The design of antiparallel coiled coils. Curr. Opin. Struct. Biol. 2001; 11: 450-457.
28. Yu YB. Coiled-coils: stability, specificity, and drug delivery potential. Adv. Drug Deliv. Rev. 2002; 54:1113-1129.
29. Lupas AN, Gruber M. The structure of alpha-helical coiled coils. In Fibrous Proteins: Coiled-coils, Collagen and Elastomers, Vol. 70, Parry DAD, Squire P (eds). Academic Press: St Louis, Missouri, 2005; 37-79.
30. Sreerama N. Software and related literature located at the website http://lamar.colostate.edu/~sreeram/CDPro. [Last accessed: November 2007].
31. Cohn EJ, Edsall JT. Proteins, Amino Acids, and Peptides as Ions and Dipolar Ions. Hafner Publishing: New York, 1965.
32. Laue TM, Shah BD, Ridgeway TM, Pelletier SL. Computer aided interpretation of analytical sedimentation data for proteins. In Analytical Ultracentrifugation in Biochemistry and Polymer Science, Harding S, Rowe A, Horton J (eds). Royal Society of Chemistry: Cambridge, 1992; 90-125.
33. Peticolas WL. Raman spectroscopy of DNA and proteins. Methods in Enzymology, Vol. 246. Academic Press: San Diego, CA, 1995; 389-416.
34. Tu AT. Raman Spectroscopy in Biology: Principles and Applications. John Wiley and Sons: New York, 1982.
35. Jung C. Insight into protein structure and protein-ligand recognition by Fourier transform infrared spectroscopy. J. Mol. Recognit. 2000; 13: 325-351.
36. Ismail AA, Mantsch HH, Wong PTT. Aggregation of chymotrypsinogen: portrait by infrared spectroscopy. Biochim. Biophys. Acta 1992; 1121: 183-188.
37. Panick G, Malessa R, Winter R. Differences between the pressure-and temperature-induced denaturation and aggregation of b-lactoglobulin A, B and AB monitored by FT-IR spectroscopy and small-angle X-ray scattering. Biochemistry 1999; 38:65 12-6519.
38. Pelton JT, McLean LR. Spectroscopic methods for analysis of protein secondary structure. Anal. Biochem. 2000; 277: 167-176.
39. Zheng R, Zheng X, Dong J, Carey PR. Proteins can convert to b-sheet in single crystals. Prot. Sci. 2004; 13: 1288-1294.
40. Benaki DC, Aggeli A, Chryssikos GD, Yiannopoulos YD, Kamitsos EI, Brumley E, Case ST, Boden N, Hamodrakas S. Laser-Raman and FT-IR spectroscopic studies of peptide-analogues of silkmoth chorion protein segments. Int. J. Biol. Macromol. 1998; 23: 49-59.
41. Pauthe E, Dauchez M, Mejri M, Berjot M, Mathlouthi M, Larreta-Garde V, Alix AJP. Structural studies of a small (linear, cyclic} peptide as a synthetic substrate for thermolysin. J. Mol. Struct. 1999; 480-481: 423-426.
42. Kim SK, Kim MS, Suh SW. Surface-enhanced Raman Scattering (SERS) of aromatic amino acids and their glycyl dipeptides in silver sol. J. Raman Spectrosc. 1987; 18: 171-175.
43. Forbes RT, Barry BW, Elkordy AA. Preparation and characterisation of spray-dried and crystallised trypsin: FT-Raman study to detect protein denaturation after thermal stress. Eur. J. Pharm. Sci. 2007; 30: 315-323.
44. Chikishev AY, Lucassen GW, Koroteev NL, Otto C, Grevet J. Polarization sensitive coherent anti-Stokes Raman scattering spectroscopy of the amide I band of proteins in solutions. Biophys. J. 1992; 63: 976-985.
45. Jackson M, Haris PI, Chapman D. Conformational transitions in poly(L-lysine)-studies using Fourier transform infra-red spectroscopy. Biochim. Biophys. Acta 1989; 998: 75-79.
46. Waldner JC, Lahr SJ, Edgell MH, Pielak GJ. Nonideality and protein thermal denaturation. Biopolymers 1999; 49: 471-479.
47. Behlke J, Ristau O. Analysis of the thermodynamic non-ideality of proteins by sedimentation equilibrium experiments. Biophys. Chem. 1999; 76: 13-23.
48. Tanford C. Physical Chemistry of Macromolecules. John Wiley and Sons: New York, 1961.
49. Strano MS, Moore VC, Miller MK, Allen MJ, Haroz EH, Kittrell C, Hauge RH, Smalley RE. The role of surfactant adsorption during Ultrasonication in the dispersion of single-walled carbon nanotubes. J. Nanosci. Nanotechnol. 2003; 3: 81-86.
50. Yu ZH, Brus LE. (n,m) Structural assignments and chirality dependence in single-wall carbon nanotube Raman scattering. J. Phys. Chem. B 2001; 105: 6831-6837.
51. Brown SDM, Jorio A, Corio P, Dresselhaus MS, Dresselhaus G, Saito R, Kneipp K. Origin of the Breit-Wigner-Fano lineshape of the tangential G-band feature of metallic carbon nanotubes. Phys. Rev., B 2001; 63: 155414(1)-155414(8).
52. Sauvafol JL, Anglaret E, Rols S, Alvarez L. Phonons in single wan carbon nanotube bundles. Carbon 2002; 40: 1697-1714.
53. Souza AG, Jorio A, Swan AK, Unlu MS, Goldberg BB, Saito R, Hafner JH, Lieber CM, Pimenta MA, Dresselhaus G, Dresselhaus MS. Anomalous two-peak G '-band Raman effect in one isolated single-wall carbon nanotube. Phys. Rev., B 2002; 65: 085417(1)-085417(8).
54. Saito R, Grueneis A, Cancado LG, Pimenta MA, Jorio A, Dresselhaus G, Dresselhaus MS, Souza AG. Double resonance Raman spectra in disordered graphite and single wall carbon nanotubes. Mol. Cryst. Liq. Cryst. 2002; 387: 287-296.
55. Dresselhaus MS, Dresselhaus G, Jorio A, Souza AG, Saito R. Raman spectroscopy on isolated single wall carbon nanotubes. Carbon 2002; 40: 2043-2061.
56. Dresselhaus MS, Jorio A, Dresselhaus G, Saito R, Souza AG, Pimenta MA. Raman spectroscopy of nanoscale carbons and of an isolated carbon nanotube. Mol. Cryst. Liq. Cryst. 2002; 387: 245-253.
57. Kuzmany H, Pfeiffer R, Hulman M, Kramberger C. Raman spectroscopy of fullerenes and fullerene-nanotube composites. Philos. Trans. R. Soc. Lond. A 2004; 362: 2375-2406.
58. Saito R, Dresselhaus G, Dresselhaus MS. Physical Properties of Carbon Nanotubes. Imperial College Press: London, 1998.
59. Bachilo SM, Strano MS, Kittrell C, Hauge RH, Smalley RE, Weisman RB. Structure-assigned optical spectra of single-walled carbon nanotubes. Science 2002; 298: 2361-2366.
60. Strano MS. Probing chiral selective reactions using a revised Kataura plot for the interpretation of single-walled carbon nanotube spectroscopy. J. Am. Chem. Soc. 2003; 125: 16148-16153.
61. Alvarez WE, Pompeo F, Herrera JE, Balzano L, Resasco DE. Characterization of single-walled carbon nanotubes (SWNTs} produced by CO disproportionation on Co-Mo catalysts. Chem. Mater. 2002; 14: 1853-1858.
62. Resasco DE, Herrera JE. Structural characterization of single-walled carbon nanotubes. In Encyclopedia of Nanoscience and Nanotechnology, Vol. 10. American Scientific Publishers: Valencia, CA, 2004; 125-147.
63. Ortiz-Acevedo A, Xie H, Zorbas V, Sampson WM, Dalton AB, Baughman RH, Draper RK, Musselman IH, Dieckmann GR. Diameter-selective solubilization of single-walled carbon Nanotubes by reversible cyclic peptides. J. Am Chem. Soc. 2005; 127: 9512-9517.
64. Byler D-M, Susi H. Examination of the secondary structure of proteins by deconvolved FTIR spectra. Biopolymers 1986; 25: 469-487.
65. Surewicz WK, Mantsch HH, Chapman D. Determination of protein secondary structure by Fourier transform infrared spectroscopy: a critical assessment. Biochemistry 1993; 32: 389-394.
66. Bandekar J, Krimm S. Vibrational analysis of peptides, polypeptides and proteins: characteristic amide bands of β-turns. Proc. Natl. Acad. Sci, U.S.A. 1979; 76: 774-777.
67. Parker FS. Applications of Infrared, Raman, and Resonance Raman Spectroscopy in Biochemistry. Plenum: New York, 1983.