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Ring-Opening Polymerization of N-Carboxyanhydrides for Preparation of Polypeptides and Polypeptide-Based Hybrid Materials with Various Molecular Architectures

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Anionic Polymerization

Abstract

Different synthetic approaches utilizing ring-opening polymerization of N-carboxyanhydrides for preparation of polypeptide and polypeptide-based hybrid materials with various molecular architectures are described. An overview of polymerization mechanisms using conventional (various amines) as well as some recently developed initiators (hexamethyldisilazane, N-heterocyclic persistent carbenes, etc.) is presented, and their benefits and drawbacks for preparation of polypeptides with well-defined chain lengths and chain-end functionality are discussed. Recent examples from literature are used to illustrate different possibilities for synthesis of pure polypeptide materials with different molecular architectures bearing various functional groups, which are introduced either by modification of amino acids, before they are transformed into corresponding N-carboxyanhydrides, or by post-polymerization modifications using protective groups and/or orthogonal functional groups. Different approaches for preparation of polypeptide-based hybrid materials are discussed as well using examples from recent literature. Syntheses of simple block copolymers or copolymers with more complex molecular architectures (graft and star copolymers) as well as modifications of nanoparticles and other surfaces with polypeptides are described.

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Author information

Authors and Affiliations

  1. Division of Physical Sciences and Engineering, KAUST Catalysis Center (KCC), Polymer Synthesis Laboratory, King Abdullah University of Science and Technology (KAUST), Thuwal, Saudi Arabia

    David Pahovnik & Nikos Hadjichristidis

Authors
  1. David Pahovnik
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  2. Nikos Hadjichristidis
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Corresponding author

Correspondence to Nikos Hadjichristidis .

Editor information

Editors and Affiliations

  1. King Abdullah University of Science and Technology (KAUST), Thuwal, Saudi Arabia

    Nikos Hadjichristidis

  2. Tokyo Institute of Technology, Tokyo, Japan

    Akira Hirao

Abbreviations

Abbreviations

AMM:

Activated monomer mechanism

Bipy:

2,2′-bipyridyl

COD:

1,5-cyclooctadiene

Đ M :

Dispersity

DTT:

Dithiothreitol

HMDS:

Hexamethyldisilazane

HIPE:

High internal phase emulsion

LCST:

Lower critical solution temperature

NAM:

Normal amine mechanism

NCA:

N-carboxyanhydrides

NHC:

N-heterocyclic persistent carbenes

P(α-MeS):

Poly(α-methylstyrene)

PAla:

Polyalanine

PBLG:

Poly(γ-benzyl-L-glutamate)

PBLL:

Poly(ε-tert-butyloxycarbonyl-L-lysine)

pDNA:

Plasmid deoxyribonucleic acid

PEO:

Poly(ethylene oxide)

PI:

Polyisoprene

PLEU:

Poly(L-leucine)

PLGA:

Poly(L-glutamic acid)

PLL:

Poly(L-lysine)

POBT:

Poly(O-benzyl-L-tyrosine)

PS:

Polystyrene

PZLL:

Poly(ε-benzyloxycarbonyl-L-lysine)

RAFT:

Reversible addition–fragmentation chain transfer

ROP:

Ring-opening polymerization

SET-LRP:

Single-electron transfer-living radical polymerization

siRNA:

Small interfering ribonucleic acid

SWNT:

Single-wall carbon nanotubes

TMS:

Trimethylsilyl

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Pahovnik, D., Hadjichristidis, N. (2015). Ring-Opening Polymerization of N-Carboxyanhydrides for Preparation of Polypeptides and Polypeptide-Based Hybrid Materials with Various Molecular Architectures. In: Hadjichristidis, N., Hirao, A. (eds) Anionic Polymerization. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54186-8_6

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