Templated polymerizations on solid supports mediated by complementary nucleoside interactions

Garcia, Margarita; Kempe, Kristian; Haddleton, David M.; Khan, Afzal; Marsh, Andrew

doi:10.1039/c4py01783h

Cited by 20 publications

(28 citation statements)

References 59 publications

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“…Directly inspired by biologically accessible DNA systems—for example, nucleobase-coded chains—sequence-defined macromolecules have been synthesized employing template-based coding strategies26272829 or via the generation of regulated sequence alternating thymine hybrid polymers30, as well as the design of reactions with iterative protection/deprotection steps on supports3132. Further, bulk reactions have been conducted in flow systems based on iterative synthesis33.…”

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confidence: 99%

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

et al. 2016

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Designing artificial macromolecules with absolute sequence order represents a considerable challenge. Here we report an advanced light-induced avenue to monodisperse sequence-defined functional linear macromolecules up to decamers via a unique photochemical approach. The versatility of the synthetic strategy—combining sequential and modular concepts—enables the synthesis of perfect macromolecules varying in chemical constitution and topology. Specific functions are placed at arbitrary positions along the chain via the successive addition of monomer units and blocks, leading to a library of functional homopolymers, alternating copolymers and block copolymers. The in-depth characterization of each sequence-defined chain confirms the precision nature of the macromolecules. Decoding of the functional information contained in the molecular structure is achieved via tandem mass spectrometry without recourse to their synthetic history, showing that the sequence information can be read. We submit that the presented photochemical strategy is a viable and advanced concept for coding individual monomer units along a macromolecular chain.

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confidence: 99%

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

et al. 2016

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“…The two polymers interact in solution, probably through a mixture of hydrogen bonding and stacking interactions. Further synthetic developments using the monomers herein, studies into template directed polymerisations [41,[45][46][47][48] and interactions with single and double stranded nucleic acids of nucleoside containing copolymers in aqueous solutions are the subject of ongoing work.…”

Section: Discussionmentioning

confidence: 99%

“…1) in solution [34], and on a solid support [35]. Recently, there has been renewed interest in these types of polymers in order to use H-bonding to give sequence (and potentially stereo) control, single chain manipulation and controlled polymer folding using different controlled polymerization techniques [36], such as reversible addition-fragmentation chain transfer (RAFT) polymerization [37], nitroxidemediated polymerization [38] and ATRP [39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Water soluble triblock and pentablock poly(methacryloyl nucleosides) from copper-mediated living radical polymerisation using PEG macroinitiators

Garcia

Beecham

Kempe

et al. 2015

European Polymer Journal

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a b s t r a c tThe monomers methacryloyl uridine and methacryloyl adenosine have been polymerised under copper-mediated living radical conditions using poly(ethylene glycol) (PEG) macroinitiators to give triblock and pentablock copolymers of reasonable dispersity. The triblocks were used as initiators for the successful synthesis of pentablock copolymers. The secondary structures of the triblock and pentablock copolymers have been investigated using circular dichroism (CD) spectroscopy. The adenosine copolymers are found to exhibit more ordered secondary structures in water in comparison to the uridine derived polymers. New supramolecular structure is observed by CD upon mixing adenosine and uridine triblock copolymers in water. The polymers obtained are of interest as potential drug delivery agents through interaction with small molecules and oligonucelotides.

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“…Another concept which may offer a means to control chain growth is templated polymerization—an example from Nature is the transcription of nuclear DNA to messenger RNA. Various templating approaches have been developed in synthetic polymer chemistry, exploiting interactions such as hydrogen bonding . To date, generally only limited levels of control have been achieved based on templating methods, probably due to interactions of highly active propagating radicals between different templates in a homogeneous system.…”

Section: Introductionmentioning

confidence: 99%

“…To date, generally only limited levels of control have been achieved based on templating methods, probably due to interactions of highly active propagating radicals between different templates in a homogeneous system. In a recent study, polymer particles as solid supports with covalently attached poly(methacryloyl nucleosides) template chains were used for templated polymerization of complementary nucleoside methacrylate monomers, demonstrating the ability to polymerize mainly templating monomer from a monomer mixture containing also nontemplating monomer …”

Section: Introductionmentioning

confidence: 99%

Revised insights into templating radical polymerization within nanoreactors

Tardy

Bhullar

Lim

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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The field of polymer chemistry is currently experiencing major research efforts into development of novel techniques for synthesis of polymers with well‐controlled microstructure. Recently, a new method has been reported [McHale et al., Nat. Chem. 2012, 4, 491–497] whereby high molecular weight and low dispersity polymer can be obtained by a radical polymerization process via the use of solely physico‐chemical interactions. This work was based on the combination of H‐bonding templated polymerization confined within nanoreactors of self‐assembled block copolymers. Herein, this system is thoroughly investigated to fully elucidate the underlying mechanism. Modification of physico‐chemical parameters, kinetic parameters as well as observations of size exclusion chromatography (SEC) results and colloidal behavior in various solvents provide revised insights into the mechanism. Through detailed NMR and SEC investigations, it is demonstrated that the SEC secondary peak originally believed to be the high molecular weight “daughter” polymer actually corresponds to nanoparticles containing the daughter polymer. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1590–1600

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Templated polymerizations on solid supports mediated by complementary nucleoside interactions

Abstract: The preparation of immobilized poly(methacryloyl nucleosides) and their abilities for template polymerizations is discussed.

Cited by 20 publications

References 59 publications

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

Water soluble triblock and pentablock poly(methacryloyl nucleosides) from copper-mediated living radical polymerisation using PEG macroinitiators

Revised insights into templating radical polymerization within nanoreactors

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