High‐Purity Discrete PEG‐Oligomer Crystals Allow Structural Insight

French, Alister C.; Thompson, Amber L.; Davis, Benjamin G.

doi:10.1002/anie.200804623

Cited by 147 publications

(135 citation statements)

References 44 publications

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“…Despite the high MW impurity the molecular weight distribution stayed narrow (Table 1). While the use of the tert-butoxy unit as protective group is known for ethylene oxide oligomers 20 it has not been used for secondary polyethers like PPO or PBO. The selectivity of the ether cleavage in ethylene oxide based compounds can be expected due to the much lower reactivity of primary ethers compared to the tertiary ether of the tert-butyl Scheme 2 Synthesis of OH-functionalized poly(1,2-butylene oxide)s. end-group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and rheological behavior of poly(1,2-butylene oxide) based supramolecular architectures

et al. 2016

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In this work we present the synthesis of poly(1,2-butylene oxide) (PBO) functionalized with the complementary hydrogen bond forming groups 2,4-diaminotriazine (DAT) and thymine. PBO is a rubbery polymer. Due to its semi-polar nature PBO is expected to suppresses non-directed cluster formation of the supramolecular groups but not influence their directed interactions. For the synthesis of backbone functionalized polymers we developed a procedure which allowed randomly copolymerizing BO with 1,2-epoxy-7-octene using anionic ring opening polymerization with potassium tert-butanolate as initiator. The vinyl groups were converted to OH-groups by oxidation. In addition, PBO with one alcoholic end group was obtained by homopolymerization of BO. For the variant with OH-groups at both chain ends a procedure was developed which was based on the cleavage of the tert-butyl initiator group. In all the polymers the alcohol groups were basically quantitatively transformed into NH 2 -groups.DAT and thymine functionalities were attached to the NH 2 -groups again in almost quantitative conversion. All reaction steps were monitored by 1 H-NMR using pyridine-d 5 as solvent. This method allowed determining the conversions of the different synthesis steps with high precision. The materials were examined in linear rheology in order to study the effect of the hydrogen-bonds on the dynamics of the resulting supramolecular structures. The results corroborate the exclusive existence of directed interactions between the supramolecular groups.

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Section: Resultsmentioning

confidence: 99%

Synthesis and rheological behavior of poly(1,2-butylene oxide) based supramolecular architectures

et al. 2016

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“…Recently published crystallographic data of a PEG molecule [22] was used to build reference structures. The geometric parameters (dihedral angles, bond angles, bond lengths) of the crystallographic record were measured and PEG-molecules with 6 to 81 subunits constructed accordingly.…”

Section: Methodsmentioning

confidence: 99%

“…In order to verify the structural data resulting from such MD simulations, experimentally determined structures are needed. There have been several reports of 3D structural data of PEG [21] with the recent addition of a high quality crystallographic record [22]. …”

Section: Introductionmentioning

confidence: 99%

Molecular dynamics simulations on aqueous two-phase systems - Single PEG-molecules in solution

2012

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BackgroundMolecular Dynamics (MD) simulations are a promising tool to generate molecular understanding of processes related to the purification of proteins. Polyethylene glycols (PEG) of various length are commonly used in the production and purification of proteins. The molecular mechanisms behind PEG driven precipitation, aqueous two-phase formation or the effects of PEGylation are however still poorly understood.ResultsIn this paper, we ran MD simulations of single PEG molecules of variable length in explicitly simulated water. The resulting structures are in good agreement with experimentally determined 3D structures of PEG. The increase in surface hydrophobicity of PEG of longer chain length could be explained on an atomic scale. PEG-water interactions as well as aqueous two-phase formation in the presence of PO4 were found to be correlated to PEG surface hydrophobicity.ConclusionsWe were able to show that the taken MD simulation approach is capable of generating both structural data as well as molecule descriptors in agreement with experimental data. Thus, we are confident of having a good in silico representation of PEG.

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“…29 2-Bromo-7-iodofluorene with octa(ethylene glycol) monomethyl ether chains at the 9,9'-positions was therefore selected. The octa(ethylene glycol) chain was synthesized from two tetra(ethylene glycol) subunits, 30 as illustrated in Scheme 3. First, tosyl groups were installed on both ends of tetra(ethylene glycol) by treatment with tosyl chloride to give the bis(tosylate) 8.…”

Section: (B) Application Of Compound 4 For the Synthesis Of Selectivementioning

confidence: 99%

Ring Walking/Oxidative Addition Reactions for the Controlled Synthesis of Conjugated Polymers

Bazan¹

2012

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High‐Purity Discrete PEG‐Oligomer Crystals Allow Structural Insight

Cited by 147 publications

References 44 publications

Synthesis and rheological behavior of poly(1,2-butylene oxide) based supramolecular architectures

Synthesis and rheological behavior of poly(1,2-butylene oxide) based supramolecular architectures

Molecular dynamics simulations on aqueous two-phase systems - Single PEG-molecules in solution

Ring Walking/Oxidative Addition Reactions for the Controlled Synthesis of Conjugated Polymers

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