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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Comb. Sci. 2018, 20, 8, 492-498
    Research Article

    Sustainable Flow Synthesis of Encoded Beads for Combinatorial Chemistry and Chemical Biology
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    • Hongxia Hu
      Hongxia Hu
      Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
      More by Hongxia Hu
    • Sergei Nikitin
      Sergei Nikitin
      Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
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      Orcidhttp://orcid.org/0000-0001-7630-7816
    • Adam Bjørnholdt Berthelsen
      Adam Bjørnholdt Berthelsen
      Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
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    • Frederik Diness
      Frederik Diness
      Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
      More by Frederik Diness
      Orcidhttp://orcid.org/0000-0001-5098-7198
    • Sanne Schoffelen
      Sanne Schoffelen
      Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
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      Orcidhttp://orcid.org/0000-0003-2664-8561
    • Morten Meldal*
      Morten Meldal
      Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
      *E-mail: [email protected]
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      Orcidhttp://orcid.org/0000-0001-6114-9018
    Other Access OptionsSupporting Information (1)

    ACS Combinatorial Science

    Cite this: ACS Comb. Sci. 2018, 20, 8, 492–498
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    https://doi.org/10.1021/acscombsci.8b00052
    Published July 3, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    Monosized beads of polar resins were synthesized for combinatorial chemistry and chemical biology by sustainable microchannel flow synthesis. Regular, biocompatible, and optically encoded beads could be efficiently prepared on large scale and in high yield. In a preparative flow polymerization instrument, taking advantage of a designed T-connector for droplet formation, quality beads were synthesized with accurate size control using a minimal amount of recirculating silicon oil as suspension medium. Bead-size was controlled through shear imposed by the silicon oil flow rate. This process provided 86% yield of ∼500 μm macrobeads beads within a 20 μm size range with no deformities or vacuoles, ideally suited for combinatorial chemistry and protein binding studies. The simple flow equipment consisted of a syringe pump for monomer and initiator delivery, a T-connector, a gear pump for oil recirculation, a long, heated coil of Teflon tubing and a collector syringe. The method was used for preparation of PEGA1900 beads, optically encoded with fluorescent microparticles. The microparticle matrix (MPM) encoded beads were tested in a MPM-decoder showing excellent recognition in bead decoding.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscombsci.8b00052.

    • Experimental procedures, materials and instrumentation, synthesis of bis-acrylamidopropyl polyethylene glycol (1900), (Acr)2PEG1900, encoded beads by radical inverse suspension polymerization in silicon oil, optimizations, determination of functional loading in beads, decoding, chemistry of the encoding process, encoded beads obtained by bulk inverse radical polymerization, encoded beads from controlled addition to a bulk reactor, distribution of microparticles from controlled addition, product from controlled addition to a stirred reactor, determination of linear flow rates generated by gear pump, tabulated data, flow synthesis of encoded beads at 220 mm/s, flow synthesis of encoded beads at 140 mm/s, image of beads, data from the decoding of 323 encoded beads, overlaid images from fitting of image sets for 323 beads, and measurement of bead size and SDOM (PDF)

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    This article is cited by 9 publications.

    1. Mads Liep Ramsing, Christoffer Warming, Morten Meldal. Green Resins for All: Sustainable Preparation of PEGA Resin for Peptide and Protein Synthesis and Immobilization. ACS Applied Materials & Interfaces 2025, 17 (17) , 25764-25773. https://doi.org/10.1021/acsami.5c01951
    2. Milan M. Fowkes, Linda Troeberg, Paul E. Brennan, Tonia L. Vincent, Morten Meldal, Ngee H. Lim. Development of Selective ADAMTS-5 Peptide Substrates to Monitor Proteinase Activity. Journal of Medicinal Chemistry 2023, 66 (5) , 3522-3539. https://doi.org/10.1021/acs.jmedchem.2c02090
    3. Daniel Madsen, Frederik P. Jørgensen, Daniel Palmer, Milena E. Roux, Jakob V. Olsen, Mikael Bols, Sanne Schoffelen, Frederik Diness, Morten Meldal. Design and Combinatorial Development of Shield-1 Peptide Mimetics Binding to Destabilized FKBP12. ACS Combinatorial Science 2020, 22 (3) , 156-164. https://doi.org/10.1021/acscombsci.9b00197
    4. Hongxia Hu, Christian Kofoed, Ming Li, Juliana Pereira Lopes Gonçalves, Jonas Hansen, Martin Wolfram, Axel Kornerup Hansen, Camilla Hartmann Friis Hansen, Frederik Diness, Sanne Schoffelen, Morten Meldal. Computational Evolution of Threonine-Rich β-Hairpin Peptides Mimicking Specificity and Affinity of Antibodies. ACS Central Science 2019, 5 (2) , 259-269. https://doi.org/10.1021/acscentsci.8b00614
    5. Kinshuk Ghosh, William D. Lubell. N ‐ to C ‐Peptide Synthesis, Arguably the Future for Sustainable Production. Journal of Peptide Science 2025, 31 (6) https://doi.org/10.1002/psc.70019
    6. Daniela Kalafatovic, Goran Mauša, Dina Rešetar Maslov, Ernest Giralt. Bottom-Up Design Approach for OBOC Peptide Libraries. Molecules 2020, 25 (15) , 3316. https://doi.org/10.3390/molecules25153316
    7. Laurens Brocken, Ian R. Baxendale. Ionic Polymerisation and New Approaches to Polymerisation under Flow Conditions. 2019, 257-315. https://doi.org/10.1039/9781788016094-00257
    8. M. Musawwer Khan, Saigal, Sarfaraz Khan. One‐Pot Knoevenagel–Michael–Cyclization Cascade Reaction for the Synthesis of Functionalized Novel 4 H ‐pyrans by Using ZnCl 2 as a Catalyst. Journal of Heterocyclic Chemistry 2019, 56 (3) , 1020-1029. https://doi.org/10.1002/jhet.3486
    9. Jennifer N. Andexer, Uwe Beifuss, Florian Beuerle, Malte Brasholz, Rolf Breinbauer, Martin Ernst, Tobias A. M. Gulder, Stephanie Kath‐Schorr, Markus Kordes, Matthias Lehmann, Thomas Lindel, Steffen Lüdeke, Burkhard Luy, Marvin Mantel, Christian Mück‐Lichtenfeld, Claudia Muhle‐Goll, Arun Narine, Jochen Niemeyer, Roland Pfau, Jörg Pietruszka, Norbert Schaschke, Mathias O. Senge, Bernd F. Straub, Thomas Werner, Daniel B. Werz, Christian Winter. Trendbericht Organische Chemie. Nachrichten aus der Chemie 2019, 67 (3) , 46-78. https://doi.org/10.1002/nadc.20194085243
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    ACS Combinatorial Science

    Cite this: ACS Comb. Sci. 2018, 20, 8, 492–498
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscombsci.8b00052
    Published July 3, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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