Bio-synthetic Polymer Conjugates

201 Pages·2013·4.316 MB·English

by  Henning Menzel (auth.), Helmut Schlaad (eds.)

253
Advances in Polymer Science
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Helmut Schlaad
Editor
Bio-synthetic Polymer
Conjugates
With contributions by
(cid:1) (cid:1) (cid:1) (cid:1)
N.R. Cameron A.M. Eissa N. Gour B. Jung
(cid:1) (cid:1) (cid:1) (cid:1)
D. Kedracki H. Menzel K.X. Ngo I. Safir
(cid:1) (cid:1) (cid:1)
H. Schlaad P. Theato C.Vebert-Nardin J. Zhao
Editor
HelmutSchlaad
MaxPlanckInstituteofColloidsandInterfaces
ResearchCampusGolm
14424Potsdam
Germany
ISSN0065-3195 ISSN1436-5030(electronic)
ISBN978-3-642-34349-0 ISBN978-3-642-34350-6(eBook)
DOI10.1007/978-3-642-34350-6
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Preface
Biosynthetic polymer conjugates (also known as biological-synthetic polymers,
biohybrid polymers, or polymer chimeras) are polymers containing biological
segments – mostly polypeptides, proteins, polysaccharides, polynucleotides, and
terpenes–andsyntheticsegments.Theideaoraimistosynergisticallycombinethe
advantageous properties of both components, which include biological function,
molecularrecognition,chirality,biocompatibilityofthebiologicalcomponentand
solutionproperties,andprocessabilityofthesyntheticcomponent,therebycreating
new biomaterials with sophisticated properties and structural features. Conjugate
polymers are often designed for life science or biomedical applications (for in-
stance, as smart carrier systems in targeted drug or gene delivery) and also have
great potential for materialsscience (like for the production ofbioinspired hierar-
chicalstructuresorbiominerals)andsustainablechemistry(especiallypolysacchar-
idesandpolyterpenes).
The laboratory syntheses of polypeptides and of peptide–polymer conjugates
were achieved early in the last century and developed into the sophisticated
materials they are today. Peptide sequences, oligonucleotides, and also oligosac-
charides can nowadays be readily prepared by automated solid-phase syntheses;
however,subsequentconjugationtosyntheticpolymersisoftendifficult.Here,the
very recent advances in chemoselective coupling strategies, PEGylation, and
“click” chemistry have contributed greatly to overcome these problems. Also the
synthesisofprotein–polymerconjugateshasbeenfacilitatedbymildandefficient
couplingstrategiesaswellasbythedevelopmentofcontrolledradicalpolymeriza-
tion techniques (conjugation by grafting from). The controlled synthesis of well-
definedpolyterpenesisleastdeveloped,whichisattributabletothemultifunction-
alityandalsotothelimitedsolubilityofterpenemonomers.
This volume of Advances in Polymer Science is comprised of five chapters
summarizing the state of the art in the synthesis of bioorganic–synthetic polymer
conjugates based on oligo- and polypeptides (Chap. 1, authored by Henning
Menzel),proteins(Chap.2,Bjo¨rnJungandPatrickTheato),carbohydrates(Chap.
3, Ahmed M. Eissa and Neil R. Cameron), nucleotides (Chap. 4, Corinne Vebert-
Nardinetal.),andterpenes(excludingpolyisopreneandnaturalrubber)(Chap.5,
v
vi Preface
Junpeng Zhao and Helmut Schlaad). The main focus is on synthesis, whereas
special materials properties and potential applications are not discussed in great
detail.
Iwouldliketoexpressmysincerethankstoallthecontributorsofthisvolume,
authors, and reviewers, for their excellent and stimulating work. I hope that the
articleswillbeaninspirationfornewconceptsandfurtherdevelopmentsinthefield
ofbiosyntheticpolymerconjugates.
Potsdam-Golm HelmutSchlaad
August2012
.
Contents
Polypeptide–PolymerConjugates ............................................. 1
HenningMenzel
ChemicalStrategiesfortheSynthesisofProtein–PolymerConjugates .. 37
Bjo¨rnJungandPatrickTheato
GlycopolymerConjugates .................................................... 71
AhmedM.EissaandNeilR.Cameron
DNA–PolymerConjugates:FromSynthesis,ThroughComplex
FormationandSelf-assemblytoApplications ............................. 115
DawidKedracki,Ilye`sSafir,NidhiGour,KienXuanNgo,
andCorinneVebert-Nardin
SynthesisofTerpene-BasedPolymers ...................................... 151
JunpengZhaoandHelmutSchlaad
Index .......................................................................... 191
vii
.
AdvPolymSci(2013)253:1–36
DOI:10.1007/12_2012_180
#Springer-VerlagBerlinHeidelberg2012
Publishedonline:21August2012
Polypeptide–Polymer Conjugates
HenningMenzel
Abstract Conventional block copolymers are able to self-assemble in bulk,
resulting in a microphase separation or formation of aggregates in solution.
Polypeptides show secondary structure effects and specific non-covalent inter-
actions, which can cause a specific aggregation behavior and result in interesting
supramolecular structures. Conjugation of polypeptides with simple synthetic
polymers combines these phenomena with the advantages of synthetic polymers
likesolubilityandprocessability.Variouschemicalstrategieshavebeendeveloped
forconjugatingdifferentsyntheticpolymerswithsmallerandlargerpeptides.Here,
we emphasize conjugation methods for peptides prepared by solid phase peptide
synthesis having a controlled sequence as well as for polypeptides consisting
of only one or two amino acids, which can be prepared by polymerization of
the corresponding N-carboxyanhydride. By consecutive polymerization using a
macroinitiator, block copolymers as conjugates are accessible. Different methods
using this approach are highlighted. Furthermore, examples of conjugation of
peptideswithpreformedpolymersby“click”chemistryarepresented.
Keywords Block copolymer (cid:1) Click chemistry (cid:1) Comb-shaped polymers (cid:1)
Controlled radical polymerization (cid:1) Micelles (cid:1) NCA polymerization (cid:1)
Polymersomes(cid:1)Star-shapedpolymer
Contents
1 Introduction................................................................................... 3
2 SyntheticStrategies........................................................................... 3
2.1 SynthesisofPolypeptides.............................................................. 3
H.Menzel(*)
InstituteforTechnicalChemistry,BraunschweigUniversityofTechnology,
Hans-Sommer-Strasse10,38106Braunschweig,Germany
e-mail:[email protected]
2 H.Menzel
2.2 ConjugationStrategies................................................................. 6
2.3 PeptideSynthesiswithMacroinitiators................................................ 6
2.4 PolymerSynthesiswithPolypeptideMacroinitiators................................. 14
2.5 ConjugationofPreformedPolypeptidesandPolymers............................... 23
3 Comb-ShapedPolymerswithPeptideBlocks............................................... 25
4 Star-ShapedPolymerswithPeptideBlocks................................................. 27
5 ConclusionandOutlook...................................................................... 29
References........................................................................................ 30
Abbreviations
AM Activatedmonomer
ATRP Atomtransferradicalpolymerization
BLG g-Benzyl-L-glutamate
CD Cyclodextrin
DMF Dimethylformamide
DMSO Dimethylsulfoxide
DNA Deoxyribonucleicacid
DVB Divinylbenzene
GFP Greenfluorescentprotein
GPEC Gradientpolymerelutionchromatography
HEMA Hydroxyethylmethacrylate
LC–MS Liquidchromatographycoupledwithmassspectroscopy
LCST Lowercriticalsolutiontemperature
MALDI-ToF Matrix-assisted laser desorption ionization-time of flight mass
spectroscopy
mRNA Messengerribonucleicacid
NCA N-carboxyanhydride
NIPAM N-isopropylacrylamide
NMP Nitroxide-mediatedpolymerization
P3HT Poly(3-hexylthiophene)
PAF Poly(alanine-co-phenylalanine)
PBLG Poly(g-benzyl-L-glutamate)
PDMAEMA Poly[(2-dimethylamino)ethylmethacrylate]
PDMS Poly(dimethylsiloxane)
PEG Poly(ethyleneglycol)
PEI Poly(ethyleneimine)
PEO Poly(ethyleneoxide)
PGA Poly(L-glutamicacid)
PI Poly(isoprene)
PLA Poly(lactide)
PLL Poly(L-lysine)
PMeOx Poly(2-methyl-2-oxazoline)
PMPCS Poly{2,5-bis[(4-methoxyphenyl)-oxycarbonyl]styrene}
PS Poly(styrene)