Unconventional Amphiphilic Polymers Based on Chiral Polyethylene Oxides

Janssen, Henk M.; Peeters, Emiel; Zundert, M.F. van; Genderen, Marcel H. P. van; Meijer, E. W.

doi:10.1002/anie.199701221

Cited by 15 publications

(16 citation statements)

References 47 publications

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“…Sequential elution with hexane/EtOAc (1/1)sto remove contaminantssand hexane/EtOAc (1/2)sto collect the productsgave 5.0 g (68%) of a clear oil. 1 (…”

Section: S)-1-[2-(2-(benzyloxy)ethoxy)ethoxy]-4-methylpentan-2-ol ((mentioning

confidence: 99%

“…Yield: 15.4 g (77%). 1 ( in the reaction mixture, while most of the tosylate 36 had already reacted. After 72 h and after 4 days, additional portions of tosylate 36 were added (2.7 g and 0.8 g, respectively).…”

Section: S)-1-[2-(2-(benzyloxy)ethoxy)ethoxy]propan-2-ol ((S)-16)mentioning

confidence: 99%

“…Yield: 3.7 g (90%). 1 2 mmol) were heated at reflux in 15 mL of dry THF. After 3 days the solvent was evaporated in vacuo and the resulting semisolid was suspended in 15 mL of H2O.…”

Section: -{1(s)-[[2-(benzyloxy)ethoxy]methyl]-3-methylbutoxy}-ethyl mentioning

confidence: 99%

“…Drying of the collected organic layers and evaporation of the solvent gave 0.70 g (94%) of oily product. 1 2-(Benzyloxy)ethyl Tosylate (34). 14 A 2 L flask was charged with 500 mL of tert-butanol, and tert-BuOK (56.2 g, 0.50 mol) was added in portions.…”

Section: -{1(s)-[[2-(benzyloxy)ethoxy]methyl]-3-methylbutoxy}-ethyl mentioning

confidence: 99%

“…The collected organic layers were washed with 200 mL of H2O, dried with MgSO4, and concentrated to yield 255 g (97%) of pure product. 1 2H, t, 3 J ) 4.7 Hz, CH2OTs), 3.7 (2H, t, 3 J ) 4.7 Hz, CH2CH2OTs), 2.45 (3H, s, CH3). 13 (35).…”

Section: -{1(s)-[[2-(benzyloxy)ethoxy]methyl]-3-methylbutoxy}-ethyl mentioning

confidence: 99%

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Unconventional, Amphiphilic Polymers Based on Chiral Poly(ethylene oxide) Derivatives. I. Synthesis and Characterization

et al. 1997

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The first representatives of a new class of synthetic, amphiphilic polymersspolyethylene oxide-based (PEO-based) polymers 1-3, (see Figure 2)sare introduced. These polymers are constituted in a similar way as coiled-coil-forming peptides: the polymers possess a regular repeat of apolar (A) residues in a polar (P) sequence of residues. Polymers 1-3 can thus be characterized by the formula [PAPPAPP′]n or [PAPP′]n, in which P stands for an ethylene oxide unit, P′ stands for a glycate unit, and A stands for a hydrophobically modified ethylene oxide unit. The preparation of 1-3 comprises the synthesis and SnOct2-catalyzed ring-opening polymerization of 2-oxo-crown ether monomers (SS)-4, (S)-5, and (S)-6. Alternatively, polymers 1-3 have been obtained by the polycondensation of their ω-hydroxycarboxylic acid precursors. 1 H NMR and 13 C NMR analysis as well as electrospray mass spectrometry (ES-MS) verified the integrity of the followed synthetic route and, therefore, confirmed the regular repeat of polar and apolar segments in 1-3. The critical aggregation concentrations (cac's) of 1-3 in H2O at 20°C were determined by a fluorescence study, using pyrene as an apolar fluorescent probe. The cac's (i) were strongly influenced by the size of the hydrophobic segments in the polymer and by the frequency at which these segments were repeated in the polymer and (ii) varied over a wide concentration range (i.e. polymer 1 displayed a cac of ca. 0.002 mg/mL, whereas polymer 3 showed a cac of ca. 0.15 mg/mL). Thus, tailoring of the cac is possible in these new synthetic, amphiphilic polymers.

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“…Sequential elution with hexane/EtOAc (1/1)sto remove contaminantssand hexane/EtOAc (1/2)sto collect the productsgave 5.0 g (68%) of a clear oil. 1 (…”

Section: S)-1-[2-(2-(benzyloxy)ethoxy)ethoxy]-4-methylpentan-2-ol ((mentioning

confidence: 99%

Section: S)-1-[2-(2-(benzyloxy)ethoxy)ethoxy]propan-2-ol ((S)-16)mentioning

confidence: 99%

“…Yield: 3.7 g (90%). 1 2 mmol) were heated at reflux in 15 mL of dry THF. After 3 days the solvent was evaporated in vacuo and the resulting semisolid was suspended in 15 mL of H2O.…”

Section: -{1(s)-[[2-(benzyloxy)ethoxy]methyl]-3-methylbutoxy}-ethyl mentioning

confidence: 99%

Section: -{1(s)-[[2-(benzyloxy)ethoxy]methyl]-3-methylbutoxy}-ethyl mentioning

confidence: 99%

Section: -{1(s)-[[2-(benzyloxy)ethoxy]methyl]-3-methylbutoxy}-ethyl mentioning

confidence: 99%

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Unconventional, Amphiphilic Polymers Based on Chiral Poly(ethylene oxide) Derivatives. I. Synthesis and Characterization

et al. 1997

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Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

Ikeda

Haraguchi

Numata

et al. 2007

Chemistry An Asian Journal

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We synthesized a semiartificial beta-1,3-glucan, curdlan with dialkylaniline groups (CUR-DA), that bears chromophoric aromatic groups at its peripheral positions. Spectroscopic studies as well as microscopic observations indicate that CUR-DA adopts a triple-stranded helical structure in water- or methanol-rich solutions of dimethyl sulfoxide (DMSO). This triple-stranded helical structure exhibits high thermal stability and resistance to base, attributes that are similar to those of the triple-stranded helical structure of native beta-1,3-glucans such as schizophyllan. Moreover, we found that the stability of the triple-stranded helical structure can be easily modulated by solvent composition and metal-ion (Zn2+) binding. As beta-1,3-glucan polysaccharides are known to serve as "polymeric" hosts, including certain DNA molecules, carbon nanotubes, and conjugated polymers, and complexation occurs only with the single-stranded structure, this information is very useful for the creation of these attractive polymeric composites, the controlled release of DNA, and so on.

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PEG Analogs Synthesized by Ring-Opening Metathesis Polymerization for Reversible Bioconjugation

et al. 2018

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Poly(ethylene glycols) (PEGs) with protein-reactive end-groups are widely utilized in bioconjugation reactions. Herein, we describe the use of ring-opening metathesis polymerization (ROMP) to synthesize unsaturated protein-reactive PEG analogs. These ROMP PEGs (rPEGs) contained terminal aldehyde functionality and ranged in molecular weight from 6 to 20 kDa. The polymers were readily conjugated to free amines on the protein hen egg-white lysozyme (Lyz). Biocompatibility of the unsaturated PEGs was assessed in vitro, revealing the polymers to be nontoxic up to concentrations of at least 1 mg/mL in human dermal fibroblasts (HDFs). The resulting unsaturated rPEG-lysozyme conjugates underwent metathesis-based depolymerization, resulting in decreased molecular weight of the conjugate.

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Unconventional Amphiphilic Polymers Based on Chiral Polyethylene Oxides

Cited by 15 publications

References 47 publications

Unconventional, Amphiphilic Polymers Based on Chiral Poly(ethylene oxide) Derivatives. I. Synthesis and Characterization

Unconventional, Amphiphilic Polymers Based on Chiral Poly(ethylene oxide) Derivatives. I. Synthesis and Characterization

Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

PEG Analogs Synthesized by Ring-Opening Metathesis Polymerization for Reversible Bioconjugation

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