“Inverse” synthesis of polymer bioconjugates using soluble supports

Meszyńska, Anna; Badi, Nezha; Börner, Hans G.; Lutz, Jean‐François

doi:10.1039/c2cc30233k

Cited by 38 publications

(43 citation statements)

References 38 publications

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“…Telechelic oligoamides were obtained after three amidification and two copper‐assisted alkyne‐azide cycloaddition reactions followed by cleavage with a mixture of trifluoroacetic acid and dichloromethane (TFA/DCM = 9/1). Contrary to our previous work, we were interested in using an unmodified Wang resin, strategy that will induce obtaining the targeted oligomers without any residual linker present on the oligomer …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach

Trinh

Oswald

Chan‐Seng

et al. 2013

Macromol. Rapid Commun.

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110

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A library of eight sequence-defined model oligomers, whose sequence is based on a (0,1) binary code, is prepared through chemoselective repeating cycles of amidification and copper-assisted alkyne-azide cycloaddition reactions from a non-modified Wang resin. This library is constructed from two AB (A = acid, B = alkyne) building blocks, i.e., 4-pentynoic acid and 2-methyl-4-pentynoic acid acting, respectively, as non-coding (0) and coding (1) monomer, and 1-amino-11-azido-3,6,9-trioxaundecane as complementary CD (C = amine, D = azide) spacer building block. In particular, encoded triads are synthesized by consecutive covalent attachment of five building blocks (i.e., three coding/non-coding monomers and two spacers). In this communication, optimal protocols for the synthesis of the targeted oligomers are reported along with their full characterization by (1) H NMR, MALDI-TOF mass spectrometry, and size-exclusion chromatography. It is found that all possible encoded triads (i.e., eight possibilities) could be synthesized using this approach. Indeed, monodisperse sequence-defined oligomers are prepared and characterized in all cases.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach

Trinh

Oswald

Chan‐Seng

et al. 2013

Macromol. Rapid Commun.

Self Cite

110

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“…Colonies of infected E. coli bacteria are grown and for six of these colonies the DNA was sequenced, all yielded identical amino-acid sequences: NHWSDKRAQITI. Peptides (AD, short for adhesion domain) and peptide-polymer (PEO-AD) conjugates (with a PEO block, M n = 3.2·10 3 g/mol) with this sequence were synthesized by solid-phase peptide synthesis using inverse conjugation strategies (60). Additionally, a fluorescent marker (carboxyfluorescein, abbreviated fam) and a spacer (two glycine residues) were incorporated, yielding fam-GG-NHWSDKRAQITI.…”

Section: Phage Display Assisted Design Of Bioconjugatesmentioning

confidence: 99%

Peptide-Polymer Conjugates as Model Systems To Explore the Functional Space of Precision Polymers

Brummelhuis

Wieczorek

Wilke

et al. 2014

ACS Symposium Series

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“…In a series of recent publications, we have shown that atom‐transfer radical polymerization (ATRP) is a very convenient method for preparing tailor‐made soluble polymer supports. ATRP is a controlled radical‐polymerization technique that permits fine control of the molecular structure of synthetic polymers .…”

Section: Introductionmentioning

confidence: 99%

Optimal ATRP‐Made Soluble Polymer Supports for Phosphoramidite Chemistry

Oswald

Ouahabi

Charles

et al. 2016

Chemistry A European J

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Soluble polystyrene supports with optimal molecular structures for iterative phosphoramidite chemistry were prepared by atom-transfer radical polymerization (ATRP) and subsequent chain-end modification steps. The controlled radical polymerization of styrene was first performed in the presence of an 9-fluorenylmethoxycarbonyl (Fmoc)-protected amino-functional ATRP initiator. Soluble supports of different molecular weight were prepared. Size-exclusion chromatography and NMR analysis indicated formation of well-defined polymers with controlled chain lengths and narrow dispersity. After synthesis, the bromo ω end group of the ATRP polymer was removed by dehalogenation in the presence of tributyltin hydride, and the Fmoc protecting group of the α moiety was subsequently cleaved with piperidine. The resulting α-primary amine was afterwards treated with a linker containing a carboxyl group, a cleavable ester site, and a dimethoxytrityl-protected hydroxyl group to afford ideal soluble supports for phosphoramidite chemistry. NMR analysis indicated that these chain-end modifications were quantitative. The supports were tested for the synthesis of a non-natural sequence-defined oligophosphates. High-resolution ESI-MS analysis of the cleaved oligomers indicated formation of uniform species, and thus confirmed the efficiency of the ATRP-made soluble polymer supports. In addition, the synthesis of a thymidine-loaded soluble support was achieved.

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“Inverse” synthesis of polymer bioconjugates using soluble supports

Abstract: Well-defined cleavable or non-cleavable soluble polystyrene supports were prepared by atom transfer radical polymerization and utilized for the iterative synthesis of functional hexapeptides. This approach allowed rapid and efficient liquid phase synthesis of peptide-polymer conjugates.

Cited by 38 publications

References 38 publications

Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach

Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach

Peptide-Polymer Conjugates as Model Systems To Explore the Functional Space of Precision Polymers

Optimal ATRP‐Made Soluble Polymer Supports for Phosphoramidite Chemistry

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