Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface

R. Matmour; I. Cat, de; S.J. George; W. Adriaens; P.E.L.G. Leclère; P.H.H. Bomans; N.A.J.M. Sommerdijk; J.C. Gielen; P.C.M. Christianen; J.T. Heldens; J.C.M. van Hest; D.W.P.M. Lowik; S. Feyter, de; E.W. Meijer; A.P.H.J. Schenning

doi:10.1021/ja803026j

Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface

R. Matmour, I. Cat, de, S.J. George, W. Adriaens, P.E.L.G. Leclère, P.H.H. Bomans, N.A.J.M. Sommerdijk, J.C. Gielen, P.C.M. Christianen, J.T. Heldens, J.C.M. van Hest, D.W.P.M. Lowik, S. Feyter, de, E.W. Meijer, A.P.H.J. Schenning

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Abstract

Two oligo(p-phenylenevinylene)-peptide hybrid amphiphiles have been synthesized using solid-and liquid-phase strategies. The amphiliphiles are composed of a Ï€-conjugated oligo(p-phenylenevinylene) trimer (OPV) which is coupled at either a glycinyl-alanyl-glycinyl-alanyl-glycine (GAGAG) silk-inspired +Ý-sheet or a glycinyl-alanyl-asparagyl-prolyl-asparagy- alanyl-alanyl-glycine (GANPNAAG) +Ý-turn forming oligopeptide sequence. The solid-phase strategy enables one to use longer peptides if strong acidic conditions are avoided, whereas the solution-phase coupling gives better yields. The study of the two-dimensional (2D) self-assembly of OPV-GAGAG by scanning tunneling microscopy (STM) at the submolecular level demonstrated the formation of bilayers in which the molecules are lying antiparallel in a +Ý-sheet conformation. In the case of OPV-GANPNAAG self-assembled monolayers could not be observed. Absorption, fluorescence, and circular dichroism studies showed that OPV-GAGAG and OPV-GANPNAAG are aggregated in a variety of organic solvents. In water cryogenic temperature transmission electron microscopy (cryo-TEM), atomic force microscopy (AFM), light scattering, and optical studies reveal that self-assembled nanofibers are formed in which the helical organization of the OPV segments is dictated by the peptide sequence. -© 2008 American Chemical Society

Original language	English
Pages (from-to)	14576-14583
Journal	Journal of the American Chemical Society
Volume	130
Issue number	44
DOIs	https://doi.org/10.1021/ja803026j
Publication status	Published - 2008

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Matmour, R., Cat, de, I., George, S. J., Adriaens, W., Leclère, P. E. L. G., Bomans, P. H. H., Sommerdijk, N. A. J. M., Gielen, J. C., Christianen, P. C. M., Heldens, J. T., van Hest, J. C. M., Lowik, D. W. P. M., Feyter, de, S., Meijer, E. W., & Schenning, A. P. H. J. (2008). Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface. Journal of the American Chemical Society, 130(44), 14576-14583. https://doi.org/10.1021/ja803026j

@article{4f4e275f168c45ecbce74f8f59acc09b,

title = "Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface",

abstract = "Two oligo(p-phenylenevinylene)-peptide hybrid amphiphiles have been synthesized using solid-and liquid-phase strategies. The amphiliphiles are composed of a {\"I}€-conjugated oligo(p-phenylenevinylene) trimer (OPV) which is coupled at either a glycinyl-alanyl-glycinyl-alanyl-glycine (GAGAG) silk-inspired +{\'Y}-sheet or a glycinyl-alanyl-asparagyl-prolyl-asparagy- alanyl-alanyl-glycine (GANPNAAG) +{\'Y}-turn forming oligopeptide sequence. The solid-phase strategy enables one to use longer peptides if strong acidic conditions are avoided, whereas the solution-phase coupling gives better yields. The study of the two-dimensional (2D) self-assembly of OPV-GAGAG by scanning tunneling microscopy (STM) at the submolecular level demonstrated the formation of bilayers in which the molecules are lying antiparallel in a +{\'Y}-sheet conformation. In the case of OPV-GANPNAAG self-assembled monolayers could not be observed. Absorption, fluorescence, and circular dichroism studies showed that OPV-GAGAG and OPV-GANPNAAG are aggregated in a variety of organic solvents. In water cryogenic temperature transmission electron microscopy (cryo-TEM), atomic force microscopy (AFM), light scattering, and optical studies reveal that self-assembled nanofibers are formed in which the helical organization of the OPV segments is dictated by the peptide sequence. -{\textcopyright} 2008 American Chemical Society",

author = "R. Matmour and {Cat, de}, I. and S.J. George and W. Adriaens and P.E.L.G. Lecl{\`e}re and P.H.H. Bomans and N.A.J.M. Sommerdijk and J.C. Gielen and P.C.M. Christianen and J.T. Heldens and {van Hest}, J.C.M. and D.W.P.M. Lowik and {Feyter, de}, S. and E.W. Meijer and A.P.H.J. Schenning",

year = "2008",

doi = "10.1021/ja803026j",

language = "English",

volume = "130",

pages = "14576--14583",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "44",

}

Matmour, R, Cat, de, I, George, SJ, Adriaens, W, Leclère, PELG, Bomans, PHH, Sommerdijk, NAJM, Gielen, JC, Christianen, PCM, Heldens, JT, van Hest, JCM, Lowik, DWPM, Feyter, de, S, Meijer, EW & Schenning, APHJ 2008, 'Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface', Journal of the American Chemical Society, vol. 130, no. 44, pp. 14576-14583. https://doi.org/10.1021/ja803026j

TY - JOUR

T1 - Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface

AU - Matmour, R.

AU - Cat, de, I.

AU - George, S.J.

AU - Adriaens, W.

AU - Leclère, P.E.L.G.

AU - Bomans, P.H.H.

AU - Sommerdijk, N.A.J.M.

AU - Gielen, J.C.

AU - Christianen, P.C.M.

AU - Heldens, J.T.

AU - van Hest, J.C.M.

AU - Lowik, D.W.P.M.

AU - Feyter, de, S.

AU - Meijer, E.W.

AU - Schenning, A.P.H.J.

PY - 2008

Y1 - 2008

N2 - Two oligo(p-phenylenevinylene)-peptide hybrid amphiphiles have been synthesized using solid-and liquid-phase strategies. The amphiliphiles are composed of a Ï€-conjugated oligo(p-phenylenevinylene) trimer (OPV) which is coupled at either a glycinyl-alanyl-glycinyl-alanyl-glycine (GAGAG) silk-inspired +Ý-sheet or a glycinyl-alanyl-asparagyl-prolyl-asparagy- alanyl-alanyl-glycine (GANPNAAG) +Ý-turn forming oligopeptide sequence. The solid-phase strategy enables one to use longer peptides if strong acidic conditions are avoided, whereas the solution-phase coupling gives better yields. The study of the two-dimensional (2D) self-assembly of OPV-GAGAG by scanning tunneling microscopy (STM) at the submolecular level demonstrated the formation of bilayers in which the molecules are lying antiparallel in a +Ý-sheet conformation. In the case of OPV-GANPNAAG self-assembled monolayers could not be observed. Absorption, fluorescence, and circular dichroism studies showed that OPV-GAGAG and OPV-GANPNAAG are aggregated in a variety of organic solvents. In water cryogenic temperature transmission electron microscopy (cryo-TEM), atomic force microscopy (AFM), light scattering, and optical studies reveal that self-assembled nanofibers are formed in which the helical organization of the OPV segments is dictated by the peptide sequence. -© 2008 American Chemical Society

AB - Two oligo(p-phenylenevinylene)-peptide hybrid amphiphiles have been synthesized using solid-and liquid-phase strategies. The amphiliphiles are composed of a Ï€-conjugated oligo(p-phenylenevinylene) trimer (OPV) which is coupled at either a glycinyl-alanyl-glycinyl-alanyl-glycine (GAGAG) silk-inspired +Ý-sheet or a glycinyl-alanyl-asparagyl-prolyl-asparagy- alanyl-alanyl-glycine (GANPNAAG) +Ý-turn forming oligopeptide sequence. The solid-phase strategy enables one to use longer peptides if strong acidic conditions are avoided, whereas the solution-phase coupling gives better yields. The study of the two-dimensional (2D) self-assembly of OPV-GAGAG by scanning tunneling microscopy (STM) at the submolecular level demonstrated the formation of bilayers in which the molecules are lying antiparallel in a +Ý-sheet conformation. In the case of OPV-GANPNAAG self-assembled monolayers could not be observed. Absorption, fluorescence, and circular dichroism studies showed that OPV-GAGAG and OPV-GANPNAAG are aggregated in a variety of organic solvents. In water cryogenic temperature transmission electron microscopy (cryo-TEM), atomic force microscopy (AFM), light scattering, and optical studies reveal that self-assembled nanofibers are formed in which the helical organization of the OPV segments is dictated by the peptide sequence. -© 2008 American Chemical Society

U2 - 10.1021/ja803026j

DO - 10.1021/ja803026j

M3 - Article

C2 - 18847199

SN - 0002-7863

VL - 130

SP - 14576

EP - 14583

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface

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