Water soluble azido polyisocyanides as functional beta-sheet mimics

Erik Schwartz; Matthieu Koepf; Heather J. Kitto; Mónica Espelt; Vicent J. Nebot-Carda; Rene de Gelder; Roeland J.M. Nolte; Jeroen J.L.M. Cornelissen; Alan E. Rowan

doi:10.1002/pola.23477

Water soluble azido polyisocyanides as functional beta-sheet mimics

Erik Schwartz, Matthieu Koepf, Heather J. Kitto, Mónica Espelt, Vicent J. Nebot-Carda, Rene de Gelder, Roeland J.M. Nolte, Jeroen J.L.M. Cornelissen, Alan E. Rowan

Faculty of Science and Technology

Research output: Contribution to journal › Article › Academic › peer-review

12 Citations (Scopus)

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Abstract

The design and synthesis of functional biomimetic water soluble polymers with a defined secondary structure has been developed using β-sheet polyisocyanopeptide scaffolds. Water soluble isocyanopolymers were prepared by random copolymerisation of the azido functionalized isocyanopeptides with nonfunctionalised methyl ester isocyanides derived from alanine. Upon saponification of the latter function a rigid rod water soluble polymer was obtained with an accessible azide for postfunctionalization. The potential of these biomimetic polymers was successfully demonstrated by using the click chemistry reaction of these polymers with an acetylene functionalised rhodamine dye.

Original language	English
Pages (from-to)	4150-4164
Number of pages	15
Journal	Journal of polymer science. Part A: Polymer chemistry
Volume	47
Issue number	16
DOIs	https://doi.org/10.1002/pola.23477
Publication status	Published - 2009

Keywords

Helical structures
Water soluble polymers
Click chemistry
Polyisocyanides
Post modification strategy
Polymers
Copolymerization
n/a OA procedure

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10.1002/pola.23477

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title = "Water soluble azido polyisocyanides as functional beta-sheet mimics",

abstract = "The design and synthesis of functional biomimetic water soluble polymers with a defined secondary structure has been developed using β-sheet polyisocyanopeptide scaffolds. Water soluble isocyanopolymers were prepared by random copolymerisation of the azido functionalized isocyanopeptides with nonfunctionalised methyl ester isocyanides derived from alanine. Upon saponification of the latter function a rigid rod water soluble polymer was obtained with an accessible azide for postfunctionalization. The potential of these biomimetic polymers was successfully demonstrated by using the click chemistry reaction of these polymers with an acetylene functionalised rhodamine dye.",

keywords = "Helical structures, Water soluble polymers, Click chemistry, Polyisocyanides, Post modification strategy, Polymers, Copolymerization, n/a OA procedure",

author = "Erik Schwartz and Matthieu Koepf and Kitto, {Heather J.} and M{\'o}nica Espelt and Nebot-Carda, {Vicent J.} and {de Gelder}, Rene and Nolte, {Roeland J.M.} and Cornelissen, {Jeroen J.L.M.} and Rowan, {Alan E.}",

year = "2009",

doi = "10.1002/pola.23477",

language = "English",

volume = "47",

pages = "4150--4164",

journal = "Journal of polymer science. Part A: Polymer chemistry",

issn = "0887-624X",

publisher = "Wiley",

number = "16",

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TY - JOUR

T1 - Water soluble azido polyisocyanides as functional beta-sheet mimics

AU - Schwartz, Erik

AU - Koepf, Matthieu

AU - Kitto, Heather J.

AU - Espelt, Mónica

AU - Nebot-Carda, Vicent J.

AU - de Gelder, Rene

AU - Nolte, Roeland J.M.

AU - Cornelissen, Jeroen J.L.M.

AU - Rowan, Alan E.

PY - 2009

Y1 - 2009

N2 - The design and synthesis of functional biomimetic water soluble polymers with a defined secondary structure has been developed using β-sheet polyisocyanopeptide scaffolds. Water soluble isocyanopolymers were prepared by random copolymerisation of the azido functionalized isocyanopeptides with nonfunctionalised methyl ester isocyanides derived from alanine. Upon saponification of the latter function a rigid rod water soluble polymer was obtained with an accessible azide for postfunctionalization. The potential of these biomimetic polymers was successfully demonstrated by using the click chemistry reaction of these polymers with an acetylene functionalised rhodamine dye.

AB - The design and synthesis of functional biomimetic water soluble polymers with a defined secondary structure has been developed using β-sheet polyisocyanopeptide scaffolds. Water soluble isocyanopolymers were prepared by random copolymerisation of the azido functionalized isocyanopeptides with nonfunctionalised methyl ester isocyanides derived from alanine. Upon saponification of the latter function a rigid rod water soluble polymer was obtained with an accessible azide for postfunctionalization. The potential of these biomimetic polymers was successfully demonstrated by using the click chemistry reaction of these polymers with an acetylene functionalised rhodamine dye.

KW - Helical structures

KW - Water soluble polymers

KW - Click chemistry

KW - Polyisocyanides

KW - Post modification strategy

KW - Polymers

KW - Copolymerization

KW - n/a OA procedure

U2 - 10.1002/pola.23477

DO - 10.1002/pola.23477

M3 - Article

SN - 0887-624X

VL - 47

SP - 4150

EP - 4164

JO - Journal of polymer science. Part A: Polymer chemistry

JF - Journal of polymer science. Part A: Polymer chemistry

IS - 16

ER -

Water soluble azido polyisocyanides as functional beta-sheet mimics

Abstract

Keywords

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