Stimuli-Responsivity of Secondary Structures of Glycopolypeptides Derived from Poly(<scp>l</scp>-glutamate-<i>co</i>-allylglycine)

Krannig, Kai-Steffen; Sun, Jing; Schlaad, Helmut

doi:10.1021/bm401883p

Cited by 48 publications

(55 citation statements)

References 23 publications

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“…This polymer (glycosylated) also proved to form stable water-soluble helices at low pH [32]. We also explored the glycosylation of poly(g-benzyl-Lglutamate-co-allylglycine) and poly(L-glutamate-co-allylglycine) [32,33]. The stimuli responsiveness of these types of block copolymers was tested by synthesizing a series of copolymers that varied in stereochemistry (using poly(L-, D-, or DL-glutamate) and block copolymer ratios).…”

Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 98%

“…Our group has recently explored the well-controlled polymerization and co-polymerization of allylglycine and its subsequent functionalization with thiol-ene chemistry [31,32]. Homo-and block copolymers were synthesized by polymerizing allylglycine NCA with hexylamine and PEG-amine (3600 g mol À1 ) [31].…”

Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 99%

“…The functionalization of sugars proved to be challenging photo-chemically (even with the addition of Irgacure ® 819 at 1 equivalent); however, quantitative functionalization of the PEG-poly(allylglycine) with sodium salt of 1-thio-b-D-glucopyranose was achieved when the thiol-ene reaction was conducted in trifluoroacetic acid for 2 days (photochemically). This polymer (glycosylated) also proved to form stable water-soluble helices at low pH [32]. We also explored the glycosylation of poly(g-benzyl-Lglutamate-co-allylglycine) and poly(L-glutamate-co-allylglycine) [32,33].…”

Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 99%

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Modification of polypeptide materials by Thiol-X chemistry

Brosnan

Schlaad

2014

Polymer

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a b s t r a c tThiol-X chemistry has proven to be a valuable toolbox for modification of peptides, proteins, monomers, and polymers. Recently, this has become especially true for the modification of polypeptides (monomers or polymers), which has resulted in a plethora of novel polymers and materials. With this in mind, this highlight focuses on the recent literature concerning the modification of polypeptides by the use of thiol-X chemistry, in particular to synthetic polypeptides either at the monomer or polymer stage modified by thiol-ene, -Michael addition, and -yne chemistries.

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Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 98%

Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 99%

Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 99%

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Modification of polypeptide materials by Thiol-X chemistry

Brosnan

Schlaad

2014

Polymer

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“…16 , 17 Special attention has also been paid to synthetic glycopolypeptides that can respond to external stimuli by conformational changes, such as to pH, temperature, or oxidation as well as their self-assembly into nanostructures. [18][19][20][21][22][23][24] Some initial studies have reported on the influence of different degrees of glycosylation on the conformation and biological properties of synthetic glycopolypeptides, 16,25 while there is no systematic study on the effect with regard to the position of the glyco units in the polypeptide.…”

Section: Introductionmentioning

confidence: 99%

Block-Sequence-Specific Glycopolypeptides with Selective Lectin Binding Properties

et al. 2017

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Glycopolypeptides with defined block sequences were prepared by sequential addition of two different N-carboxyanhydrides (NCAs), followed by selective deprotection and functionalization of pre-defined positions within the polypeptide backbone. The sequential arrangement of the galactose units and the block sequence length have been systematically varied. All the glycopolypeptides have been obtained with a similar overall composition and comparable molecular weights. Circular dichroism measurements revealed some dependence of the secondary structure on the primary composition of the glycopolypeptides at physiological pH.While statistical, diblock and tetrablock glycopolypeptides adopted random coil conformation, the octablock glycopolypeptide was mostly α-helical. The ability to selectively bind to lectins was investigated by turbidity measurements as well as Surface Plasmon Resonance (SPR) studies. 2It was found that the extent of binding was dependent on the position of the galactose units and thus the primary glycopolypeptide structure. The octablock glycopolypeptide favored interaction with lectin RCA120 while the tetrablock glycopolypeptide demonstrated the strongest binding activity to Galectin-3. The results suggest that different lectins are very sensitive to glyco coding, and that precise control of carbohydrate units in synthetic polymeric glycopeptides will remain important.

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“…H NMR spectra and 13 C NMR spectra were recorded on a Bruker AV-300 spectrometer and a Bruker AV-400 spectrometer, respectively. Matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDITOF/MS) was performed on a Bruker Autoflex III mass spectrometer in linear, positive ion mode.…”

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confidence: 99%

Controlled metal‐free polymerization toward well‐defined thermoresponsive polypeptides by polymerization at low temperature

Jiang

Wang

Zhang

et al. 2016

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

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A controlled metal-free synthetic methodology toward well-defined thermoresponsive polypeptides by decreasing the reaction temperature to 0 8C has been developed. Good control over the molecular weight in the polymerization of a trithiocarbonate-functionalized N-carboxyanhydride (MES-L-Glu-NCA) monomer was obtained using n-hexylamine as the initiator at 0 8C. It yielded homopolypeptide macrotransfer agent (PMESLG) with narrow molecular weight distribution (PDI < 1.3) and controllable chain length. Detailed 1 H NMR and MALDI-TOF-MS analysis clearly confirmed that frequently occurring side-reactions was absent at 0 8C, and the polymerization was controlled. The resultant PMESLG was applied to mediate the reversible addition-fragmentation chain transfer (RAFT) polymerization of oligo-ethylene-glycol acrylate (OEGA) for the metal-free synthesis of thermoresponsive polypeptides. These thermoresponsive polypeptides have wellcontrolled molecular weight, adopted regular a-helical conformation, and exhibited a lower critical solution temperature between 23 8C and 55 8C. To the best of our knowledge, there are very few reports about the synthesis of well-defined thermoresponsive graft polypeptides via NCA polymerization and RAFT. Consequently, this provides a new strategy for the synthesis of promising intelligent material for future biomedical applications.

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Stimuli-Responsivity of Secondary Structures of Glycopolypeptides Derived from Poly(l-glutamate-co-allylglycine)

Cited by 48 publications

References 23 publications

Modification of polypeptide materials by Thiol-X chemistry

Modification of polypeptide materials by Thiol-X chemistry

Block-Sequence-Specific Glycopolypeptides with Selective Lectin Binding Properties

Controlled metal‐free polymerization toward well‐defined thermoresponsive polypeptides by polymerization at low temperature

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