ArticleJournal of the American Chemical Society2012
Poly-amido-saccharides: synthesis via anionic polymerization of a β-lactam sugar monomer.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 88 citations in OpenAlex.
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- Clickable polyamidosaccharides: accessing bottlebrush inspired hyaluronic acid glycopolymers for CD44 targeting of breast cancer cells.Biomaterials science · 2026Article
- A General Approach to Stereoregular Pseudo-Polysaccharides: Cationic Ring-Opening Polymerization of Monosaccharide Cyclic Thionocarbonates.Journal of the American Chemical Society · 2026Article
- Synthesis of Amphiphilic Amino Poly-Amido-Saccharide and Poly(lactic) Acid Block Copolymers and Fabrication of Paclitaxel-Loaded Mucoadhesive Nanoparticles.Bioconjugate chemistry · 2024Article
- Precision native polysaccharides from living polymerization of anhydrosugars.Nature chemistry · 2023Article
- Synthesis and characterization of carbohydrate-based biosurfactant mimetics.Carbohydrate research · 2022Article
- Beyond nylon 6: polyamidesChemical Society reviews · 2022Review
- Synthesis of bioactive (1→6)-β-glucose branched poly-amido-saccharides that stimulate and induce M1 polarization in macrophages.Nature communications · 2022Article
- Sulfated poly-amido-saccharides (sulPASs) are anticoagulantsChemical science · 2021Article
- Single-crystal-to-single-crystal synthesis of a pseudostarchChemical science · 2021Article
- A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties.Angewandte Chemie (International ed. in English) · 2020Article
- The Impact of Nylon-3 Copolymer Composition on the Efficiency of siRNA Delivery to Glioblastoma Cells.Nanomaterials (Basel, Switzerland) · 2019Article
- Synthetic Biomaterials from Metabolically Derived Synthons.Chemical reviews · 2016Review
- Screening nylon-3 polymers, a new class of cationic amphiphiles, for siRNA delivery.Molecular pharmaceutics · 2015Article
- Ternary nylon-3 copolymers as host-defense peptide mimics: beyond hydrophobic and cationic subunits.Journal of the American Chemical Society · 2014Article
- Carboxylated glucuronic poly-amido-saccharides as protein stabilizing agents.Journal of the American Chemical Society · 2014Article
- Synthesis of Hydrophobic Carbohydrate Polymers and Their Formation of Thermotropic Liquid Crystalline Phases.ACS macro letters · 2014Article
- Structure-activity relationships among antifungal nylon-3 polymers: identification of materials active against drug-resistant strains of Candida albicans.Journal of the American Chemical Society · 2014Article
- Tuning the biological activity profile of antibacterial polymers via subunit substitution pattern.Journal of the American Chemical Society · 2014Article
- Synthesis of Bioinspired Carbohydrate Amphiphiles that Promote and Inhibit Biofilms.Chemical science · 2014Article
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2 authors at 1 institution in 1 country.
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Abstract
Enantiopure poly-amido-saccharides (PASs) with a defined molecular weight and narrow dispersity are synthesized using an anionic ring-opening polymerization of a β-lactam sugar monomer. The PASs have a previously unreported main chain structure that is composed of pyranose rings linked through the 1- and 2-positions by an amide with α-stereochemistry. The monomer is synthesized in one-step from benzyl-protected D-glucal and polymerized using mild reaction conditions to give degrees of polymerization ranging from 25 to >120 in high yield. Computational modeling reveals how the monomer's structure and steric bulk affect the thermodynamics and kinetics of polymerization. Protected and deprotected polymers and model compounds are characterized using a variety of methods (NMR, GPC, IR, DLS, etc.). On the basis of circular dichroism, the deprotected polymer possesses a regular secondary structure in aqueous solution, which agrees favorably with the prediction of a helical structure using molecular modeling. Furthermore, we provide evidence suggesting that the polymers bind the lectin concanavalin A at the same site as natural carbohydrates, showing the potential of these polymers to mimic natural polysaccharides. PASs offer the advantages associated with synthetic polymers, such as greater control over structure and derivitization. At the same time, they preserve many of the structural features of natural polysaccharides, such as a stereochemically regular, rigid pyranose backbone, that make natural carbohydrate polymers important materials both for their unique properties and useful applications.
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