Cysteine-containing polyisocyanides as versatile nanoplatforms for chromophoric and bioscaffolding

Severine le Gac, Stephane Le Gac, Erik Schwartz, E. Schwartz, Matthieu Koepf, Jeroen Johannes Lambertus Maria Cornelissen, Alan E. Rowan, Roeland J.M. Nolte

Research output: Contribution to journalArticleAcademicpeer-review

18 Citations (Scopus)

Abstract

The straightforward syntheses of polyisocyanides containing the alanine–cysteine motif in their side chains have been achieved. Detailed characterization of the polymers revealed a well-defined and highly stable helical conformation of the polyimine backbone responsible for the formation of rodlike structures of over one hundred nanometers. The 41 helix is further stabilized by β-sheet-like interactions between the peptide arms. As a result, the cysteine sulfur atoms are regularly aligned along the polymer axis, which provides a unique platform for the scaffolding of various entities by using versatile click-chemistry postmodification approaches. For instance, pyrene derivatives were introduced through thio-specific reactions involving either maleimide, iodoacetamide, or thioester groups, leading to arrays of stacked chromophores with excimer-like emission. A water-soluble cysteine-rich polyisocyanide was successfully biotinylated and coupled to streptavidin.
Original languageEnglish
Pages (from-to)6176-6186
Number of pages10
JournalChemistry: a European journal
Volume16
Issue number21
DOIs
Publication statusPublished - 2010

Fingerprint

Cysteine
Polymers
Iodoacetamide
Streptavidin
Pyrene
Chromophores
Sulfur
Peptides
Conformations
Derivatives
Atoms
Water
pyrene
maleimide

Keywords

  • METIS-273731
  • IR-77540
  • chromophoric scaffolding
  • helical structures
  • bioscaffolding
  • polyisocyanides
  • Click chemistry

Cite this

le Gac, Severine ; Le Gac, Stephane ; Schwartz, Erik ; Schwartz, E. ; Koepf, Matthieu ; Cornelissen, Jeroen Johannes Lambertus Maria ; Rowan, Alan E. ; Nolte, Roeland J.M. / Cysteine-containing polyisocyanides as versatile nanoplatforms for chromophoric and bioscaffolding. In: Chemistry: a European journal. 2010 ; Vol. 16, No. 21. pp. 6176-6186.
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abstract = "The straightforward syntheses of polyisocyanides containing the alanine–cysteine motif in their side chains have been achieved. Detailed characterization of the polymers revealed a well-defined and highly stable helical conformation of the polyimine backbone responsible for the formation of rodlike structures of over one hundred nanometers. The 41 helix is further stabilized by β-sheet-like interactions between the peptide arms. As a result, the cysteine sulfur atoms are regularly aligned along the polymer axis, which provides a unique platform for the scaffolding of various entities by using versatile click-chemistry postmodification approaches. For instance, pyrene derivatives were introduced through thio-specific reactions involving either maleimide, iodoacetamide, or thioester groups, leading to arrays of stacked chromophores with excimer-like emission. A water-soluble cysteine-rich polyisocyanide was successfully biotinylated and coupled to streptavidin.",
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Cysteine-containing polyisocyanides as versatile nanoplatforms for chromophoric and bioscaffolding. / le Gac, Severine; Le Gac, Stephane; Schwartz, Erik; Schwartz, E.; Koepf, Matthieu; Cornelissen, Jeroen Johannes Lambertus Maria; Rowan, Alan E.; Nolte, Roeland J.M.

In: Chemistry: a European journal, Vol. 16, No. 21, 2010, p. 6176-6186.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Cysteine-containing polyisocyanides as versatile nanoplatforms for chromophoric and bioscaffolding

AU - le Gac, Severine

AU - Le Gac, Stephane

AU - Schwartz, Erik

AU - Schwartz, E.

AU - Koepf, Matthieu

AU - Cornelissen, Jeroen Johannes Lambertus Maria

AU - Rowan, Alan E.

AU - Nolte, Roeland J.M.

PY - 2010

Y1 - 2010

N2 - The straightforward syntheses of polyisocyanides containing the alanine–cysteine motif in their side chains have been achieved. Detailed characterization of the polymers revealed a well-defined and highly stable helical conformation of the polyimine backbone responsible for the formation of rodlike structures of over one hundred nanometers. The 41 helix is further stabilized by β-sheet-like interactions between the peptide arms. As a result, the cysteine sulfur atoms are regularly aligned along the polymer axis, which provides a unique platform for the scaffolding of various entities by using versatile click-chemistry postmodification approaches. For instance, pyrene derivatives were introduced through thio-specific reactions involving either maleimide, iodoacetamide, or thioester groups, leading to arrays of stacked chromophores with excimer-like emission. A water-soluble cysteine-rich polyisocyanide was successfully biotinylated and coupled to streptavidin.

AB - The straightforward syntheses of polyisocyanides containing the alanine–cysteine motif in their side chains have been achieved. Detailed characterization of the polymers revealed a well-defined and highly stable helical conformation of the polyimine backbone responsible for the formation of rodlike structures of over one hundred nanometers. The 41 helix is further stabilized by β-sheet-like interactions between the peptide arms. As a result, the cysteine sulfur atoms are regularly aligned along the polymer axis, which provides a unique platform for the scaffolding of various entities by using versatile click-chemistry postmodification approaches. For instance, pyrene derivatives were introduced through thio-specific reactions involving either maleimide, iodoacetamide, or thioester groups, leading to arrays of stacked chromophores with excimer-like emission. A water-soluble cysteine-rich polyisocyanide was successfully biotinylated and coupled to streptavidin.

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KW - chromophoric scaffolding

KW - helical structures

KW - bioscaffolding

KW - polyisocyanides

KW - Click chemistry

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