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

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer review

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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

Originele taal-2	Engels
Pagina's (van-tot)	14576-14583
Tijdschrift	Journal of the American Chemical Society
Volume	130
Nummer van het tijdschrift	44
DOI's	https://doi.org/10.1021/ja803026j
Status	Gepubliceerd - 2008

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10.1021/ja803026j

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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, nr. 44, blz. 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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