Free radical polymerization of a sugar residue-carrying styryl monomer with a lipophilic alkoxyamine initiator: synthesis of a well-defined novel glycolipid

Ohno, Kohji; Fukuda, Takahiro; Kitano, Hiromi

doi:10.1002/(sici)1521-3935(19981001)199:10<2193::aid-macp2193>3.3.co;2-4

Cited by 4 publications

(4 citation statements)

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“…NMP has been previously applied to obtain glycopolymers and copolymers from sugar-carrying, styrene-based monomers. [38][39][40][41][42][43][44][45][46][47] This method is suitable for the synthesis of biopolymers since it does not require any catalyst or metal salt to mediate the reaction, which represents a major disadvantage for most of the other techniques. However, the employed sugar substituted monomers required significant synthetic effort.…”

Section: Introductionmentioning

confidence: 91%

Adhesion of Preosteoblasts and Fibroblasts onto Poly(pentafluorostyrene)‐Based Glycopolymeric Films and their Biocompatibility

Babiuch

Becer

Gottschaldt

et al. 2011

Macromolecular Bioscience

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An efficient and metal-catalyst free method of glycopolymer synthesis via thiol/para-fluorine "click" reaction was used to graft acetylated 1-thio-β-D-glucopyranose and 1-thio-β-D-galactopyranose onto a homopolymer of pentafluorostyrene (PFS) as well as onto a block copolymer of styrene and PFS. Subsequent deprotection of the carbohydrate moieties yielded well-defined, sugar-modified polymers (PDI < 1.2). The prepared polymers were not cytotoxic against 3T3 fibroblasts and MC3T3-E1 preosteoblasts. Furthermore, the water-insoluble copolymers were drop-cast and examined as synthetic biocompatible coatings on poly(propylene) substrates for culturing the investigated cell types. Both fibro- and preosteoblasts showed stable adhesion and proliferation on the glycopolymer-coated surfaces.

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Section: Introductionmentioning

confidence: 91%

Adhesion of Preosteoblasts and Fibroblasts onto Poly(pentafluorostyrene)‐Based Glycopolymeric Films and their Biocompatibility

Babiuch

Becer

Gottschaldt

et al. 2011

Macromolecular Bioscience

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“…Owing to their high compatibility with functional groups, the recent advent of the controlled/living free radical polymerization techniques, such as nitroxide-mediated polymerization (NMP), 23 atom transfer radical polymerization (ATRP), 24,25 or reversible addition-fragmentation chain transfer (RAFT), 26,27 has opened new prospects allowing the preparation of a wide range of tailored glycopolymer architectures. [28][29][30][31][32][33][34][35][36][37][38][39][40] However, despite the increasing attention devoted to this family of polymers, very few examples of well-defined glycopolymers have actually been reported without recourse to protecting group chemistry. Narain et al 41,42 have described the successful preparation of well defined glycopolymers by polymerization of 2-glucoamidoethyl methacrylate and 2-lactobionamidoethyl methacrylate via ATRP.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Various Glycopolymer Architectures via RAFT Polymerization: From Block Copolymers to Stars

et al. 2005

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Well-defined linear poly(acryloyl glucosamine) (PAGA) exhibiting molar masses ranging from 3 to 120 K and low polydispersities have been prepared via reversible addition-fragmentation chain transfer polymerization (RAFT) in aqueous solution without recourse to protecting group chemistry. The livingness of the process was further demonstrated by successfully chain-extending one of these polymers with N-isopropylacrylamide affording narrow dispersed thermosensitive diblocks. This strategy of polymerization was finally extended to the preparation of glycopolymer stars from Z designed non-water-soluble trifunctional RAFT agent. After the growth of very short blocks of poly(hydroxyethyl acrylate) ((-)DP(n)(branch) = 10), AGA was polymerized in aqueous solution in a controlled manner affording well-defined 3-arm glycopolymer stars.

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“…[7][8][9][10] In addition, they are potentially interesting for applications in bio-recognition where sugars play an important role. [11,12] For example, heparin is a sulfated polysaccharide belonging to the family of glycosaminoglycans, which has numerous important biological activities, associated with its interaction with different proteins. [10] In the form of glycopeptides, glycolipids, glycosaminoglycans, and proteoglycans, glycoconjugates are known to be involved in the inflammation process, [5] cell-cell interactions, [13] signal transduction, [14] cell fertility and development.…”

Section: Full Papermentioning

confidence: 99%

Thermoresponsive Glycopolymers via Controlled Radical Polymerization

Özyürek

Komber

Gramm

et al. 2007

Macro Chemistry & Physics

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New glycomonomers 3′‐(1′,2′:5′,6′‐di‐O‐isopropylidene‐α‐D‐glucofuranosyl)‐6‐methacrylamido hexanoate (MAIpGlcC5) and 3′‐(1′,2′:5′,6′‐di‐O‐isopropylidene‐α‐D‐glucofuranosyl)‐6‐methacrylamido undecanoate (MAIpGlcC10) with hydrophobic spacer units were synthesized and their homopolymers, as well as random copolymers with N‐isopropylacrylamide (NiPAAm) were prepared in varying compositions. The acidolysis of the isopropylidene protection groups of the polymers gave well‐defined sugar‐containing water‐soluble homopolymers (PMAGlcCn, n = 5, 10) and copolymers. By using the reversible addition–fragmentation chain transfer (RAFT) process, it was possible to afford these copolymers with a polydispersity index (PDI) of 1.1–1.5. Furthermore, NiPAAm homopolymers with an active chain transfer unit at the chain end could be prepared by RAFT, which were used as macro‐chain transfer agents (macro‐CTAs) to prepare a variety of sugar containing responsive block copolymers from new glycomonomers by the monomer addition concept. The cloud points of the aqueous solutions of the copolymers were strongly affected by the comonomer content, spacer chain length of the glycomonomer, and the chain architecture of the copolymers. Especially by the block copolymer concept, glycopolymers with lower critical solution temperatures (LCSTs) in the physiologically interesting range could be realized.magnified image

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Free radical polymerization of a sugar residue-carrying styryl monomer with a lipophilic alkoxyamine initiator: synthesis of a well-defined novel glycolipid

Cited by 4 publications

References 0 publications

Adhesion of Preosteoblasts and Fibroblasts onto Poly(pentafluorostyrene)‐Based Glycopolymeric Films and their Biocompatibility

Adhesion of Preosteoblasts and Fibroblasts onto Poly(pentafluorostyrene)‐Based Glycopolymeric Films and their Biocompatibility

Synthesis of Various Glycopolymer Architectures via RAFT Polymerization: From Block Copolymers to Stars

Thermoresponsive Glycopolymers via Controlled Radical Polymerization

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