Facilitated Synthesis of Heterofunctional Glycopolypeptides

Krannig, Kai-Steffen; Doriti, Afroditi; Schlaad, Helmut

doi:10.1021/ma500379m

Cited by 23 publications

(22 citation statements)

References 31 publications

(48 reference statements)

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“…In 2014, Schlaad's lab reported a possible way to streamline this process by forming glycosylated NCAs in situ, via the radical catalyzed thiol−ene reaction of allylglycine NCA (to be discussed with alkene modified NCAs in section 2.7) with 1-thio-β-D-glucopyranose-2,3,4,6-tetraacetate ( Figure 5G). 50 Allylglycine NCA, 51 although it is based on an expensive unnatural amino acid, is straightforward to prepare and purify, and 1-thio-sugars are readily available. Under optimized conditions, they found the thiol−ene conjugation reactions were able to go to completion without any attack of the thiols on the NCA monomers.…”

Section: Saccharide Modified Ncasmentioning

confidence: 99%

Synthesis of Side-Chain Modified Polypeptides

2015

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Section: Saccharide Modified Ncasmentioning

confidence: 99%

Synthesis of Side-Chain Modified Polypeptides

2015

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“…Additionally, the use of the cobalt catalyst may not be ideal for biological applications. Recently, our group has developed a nearly one-pot method for glycosylation, polymerization, and functionalization (Scheme 2) [27]. Here, instead of a cysteinederived NCA monomer (which avoids any potential ring opening by the thiol) allyl-glycine-derived NCAs were synthesized.…”

Section: Small Peptides and Monomer Modificationmentioning

confidence: 99%

“…Glycosylation was conducted using 1-thiob-D-glucopyranose or 1-thio-b-D-galactopyranose (1.5 equivalents, Scheme 2. One-pot functionalization and polymerization of glycosylated polypeptides [27].…”

Section: Polymer Modification 221 Radical Thiol-ene Additionmentioning

confidence: 99%

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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“…Recent novel studies involving the synthesis of polymers such as polyether, polyester, chitosan, polysiloxane etc., combined with polypeptide segments, have the potential to revolutionize today's morphological structures and biomedical applications . Considering conventional methods which have some drawbacks such as, multistep reactions, the use of hazardous reagents such as phosgene, lack of sufficient monomer purity and sensitivity to water contamination or heating conditions, the ideal synthetic pathway for polypeptides is the ring‐opening polymerization (ROP) of the corresponding α‐amino acids of N ‐carboxyanhydrides (NCAs) . In this technique, the polymerization can readily be induced with primary or secondary amines and their living nature allows the decisive control of molecular weight and terminal structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of polyphenylenes with polypeptide and poly(ethylene glycol) side chains

Akbulut

Endō

Yamada

et al. 2015

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

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We report a novel approach for fabrication of multifunctional conjugated polymers, namely poly(p‐phenylene)s (PPPs) possessing polypeptide (poly‐l‐lysine, PLL) and hydrophilic poly(ethylene glycol) (PEG) side chains. The approach is comprised of the combination of Suzuki coupling and in situ N‐carboxyanhydride (NCA) ring‐opening polymerization (ROP) processes. First, polypeptide macromonomer was prepared by ROP of the corresponding NCA precursor using (2,5‐dibromophenyl)methanamine as an initiator. Suzuki coupling reaction of the obtained polypeptide and PEG macromonomers both having dibromobenzene end functionality using 1,4‐benzenediboronic acid as the coupling partner in the presence of palladium catalyst gave the desired polymer. A different sequence of the same procedure was also employed to yield polymer with essentially identical structure. In the reverse sequence mode, low molar mass monomer (2,5‐dibromophenyl)methanamine, and PEG macromonomer were coupled with 1,4‐benzenediboronic acid in a similar way followed by ROP of the L‐Lysine NCA precursor through the primary amino groups of the resulting polyphenylene. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1785–1793

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Facilitated Synthesis of Heterofunctional Glycopolypeptides

Cited by 23 publications

References 31 publications

Synthesis of Side-Chain Modified Polypeptides

Synthesis of Side-Chain Modified Polypeptides

Modification of polypeptide materials by Thiol-X chemistry

Synthesis and characterization of polyphenylenes with polypeptide and poly(ethylene glycol) side chains

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