Download PDF
CC BY-NC-ND 4.0 · Synthesis 2022; 54(14): 3180-3192
DOI: 10.1055/a-1782-4224
feature

Acrylamide-Based Pd-Nanoparticle Carriers as Smart Catalysts for the Suzuki–Miyaura Cross-Coupling of Amino Acids

Viktor Sabadasch‡
a   Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Steffen Dachwitz‡
b   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Yvonne Hannappel
a   Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Thomas Hellweg∗
a   Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
c   BINAS - Bielefeld Institute for Biophysics and Nanoscience, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
,
Norbert Sewald  ∗
b   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
› Author AffiliationsWe acknowledge financial support from Deutsche Forschungsgemeinschaft (SE 609/16-1).
› Further Information
   Permissions and Reprints All articles of this category


Abstract

Polyacrylamide-based waterborne microgels were prepared with copolymerized carboxylic acid and tertiary amine moieties. The colloidal gels were loaded with palladium nanoparticles and utilized for the Suzuki–Miyaura cross-coupling of amino acids and peptides. The thermoresponsive properties of the prepared microgels were characterized by means of photon correlation spectroscopy (PCS) at solvent conditions of the catalytic reaction. The localization and morphology of the incorporated nanoparticles were characterized with transmission electron microscopy (TEM). Palladium-catalyzed Suzuki–Miyaura cross-coupling of N α-Boc-4-iodophenylalanine and N α-Boc-7-bromotryptophan with phenylboronic acid was carried out under ambient atmosphere in water at 20, 37, and 60 °C, respectively. The properties of the thermoresponsive microgel showed a strong influence on the reactivity and selectivity towards the respective substrate. For the amine containing microgels, a recyclability for up to four cycles without loss in activity could be realized. Furthermore, the systems showed good catalytic activity regarding Suzuki–Miyaura cross-coupling of halogenated amino acids in selected tri- and tetrapeptides.

Key words

palladium catalysis - bioorganic chemistry - cross-coupling - amino acids - nanoparticles - polyacrylamide microgel - halogenated peptide - polymers

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1782-4224.
  • Supporting Information


Publication History

Received: 02 December 2021

Accepted after revision: 16 February 2022

Accepted Manuscript online:
25 February 2022

Article published online:
20 April 2022

© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 2a Willemse T, Schepens W, Vlijmen H, Maes B, Ballet S. Catalysts 2017; 7: 74
      Crossref
    • 2b Gruß H, Sewald N. Chem. Eur. J. 2020; 26: 5328
      CrossrefPubMed
  • 3 Dachwitz S, Duwe DH, Wang YH, Gruß H, Hannappel Y, Hellweg T, Sewald N. Chem. Eur. J. 2020; 26: 16357
    CrossrefPubMed
  • 4 Chalker JM, Wood CS. C, Davis BG. J. Am. Chem. Soc. 2009; 131: 16346
    CrossrefPubMed
  • 5 Roy AD, Goss RJ. M, Wagner GK, Winn M. Chem. Commun. 2008; 4831
    CrossrefPubMed
  • 6 Willemse T, Van Imp K, Goss RJ. M, Van Vlijmen HW. T, Schepens W, Maes BU. W, Ballet S. ChemCatChem 2015; 7: 2055
    CrossrefPubMed
    • 7a Frese M, Schnepel C, Minges H, Voß H, Feiner R, Sewald N. ChemCatChem 2016; 8: 1799
      Crossref
    • 7b Latham J, Henry J.-M, Sharif HH, Menon BR. K, Shepherd SA, Greaney MF, Micklefield J. Nat. Commun. 2016; 7: 11873
      CrossrefPubMed
  • 8 Schnepel C, Minges H, Frese M, Sewald N. Angew. Chem. Int. Ed. 2016; 55: 14159
    CrossrefPubMed
  • 9 Sharma SV, Tong X, Pubill-Ulldemolins C, Cartmell C, Bogosyan EJ. A, Rackham EJ, Marelli E, Hamed RB, Goss RJ. M. Nat. Commun. 2017; 8: 229
    CrossrefPubMed
    • 10a Kemker I, Schnepel C, Schröder DC, Marion A, Sewald N. J. Med. Chem. 2019; 62: 7417
      CrossrefPubMed
    • 10b Kemker I, Feiner RC, Müller KM, Sewald N. ChemBioChem 2020; 21: 496
      CrossrefPubMed
  • 11 Liu C, Li X. Chem. Rec. 2016; 16: 84
    CrossrefPubMed
  • 12 Dumas A, Peramo A, Desmaële D, Couvreur P. Chimia 2016; 70: 252
    CrossrefPubMed
  • 13 Peramo A, Abdellah I, Pecnard S, Mougin J, Martini C, Couvreur P, Huc V, Desmaële D. Molecules 2020; 25: 1459
    CrossrefPubMed
  • 14 Seto H, Morii T, Yoneda T, Murakami T, Hoshino Y, Miura Y. Chem. Lett. 2013; 42: 301
    Crossref
  • 15 Pelton RH, Chibante P. Colloids Surf. 1986; 20: 247
    CrossrefPubMed
  • 16 Saunders BR, Vincent B. Adv. Colloid Interface Sci. 1999; 80: 1
    CrossrefPubMed
    • 17a Hoare T, Pelton R. Langmuir 2008; 24: 1005
      CrossrefPubMed
    • 17b Dirksen M, Kinder TA, Brändel T, Hellweg T. Molecules 2021; 26: 3181
      CrossrefPubMed
    • 18a Zhang QM, Xu W, Serpe MJ. Angew. Chem. Int. Ed. 2014; 53: 4827
      CrossrefPubMed
    • 18b Sorrell CD, Carter MC. D, Serpe MJ. Adv. Funct. Mater. 2011; 21: 425
      Crossref
    • 19a Kleinschmidt D, Fernandes MS, Mork M, Meyer AA, Krischel J, Anakhov MV, Gumerov RA, Potemkin II, Rueping M, Pich A. J. Colloid Interface Sci. 2020; 559: 76
      CrossrefPubMed
    • 19b Kleinschmidt D, Nothdurft K, Anakhov MV, Meyer AA, Mork M, Gumerov RA, Potemkin II, Richtering W, Pich A. Mater. Adv. 2020; 1: 2983
      Crossref
    • 20a Begum R, Farooqi ZH, Xiao J, Ahmed E, Sharif A, Irfan A. J. Mol. Liq. 2021; 338: 116780
      Crossref
    • 20b Besold D, Risse S, Lu Y, Dzubiella J, Ballauff M. Ind. Eng. Chem. Res. 2021; 60: 3922
      Crossref
    • 20c Roa R, Angioletti-Uberti S, Lu Y, Dzubiella J, Piazza F, Ballauff M. Z. Phys. Chem. 2018; 232: 773
      Crossref
    • 20d Mei Y, Lu Y, Polzer F, Ballauff M, Drechsler M. Chem. Mater. 2007; 19: 1062
      Crossref
    • 20e Lu Y, Proch S, Schrinner M, Drechsler M, Kempe R, Ballauff M. J. Mater. Chem. 2009; 19: 3955
      Crossref
  • 21 Wu S, Dzubiella J, Kaiser J, Drechsler M, Guo X, Ballauff M, Lu Y. Angew. Chem. Int. Ed. 2012; 51: 2229
    CrossrefPubMed
  • 22 Angioletti-Uberti S, Lu Y, Ballauff M, Dzubiella J. J. Phys. Chem. C 2015; 119: 15723
    CrossrefPubMed
    • 23a Hoare T, Pelton R. Macromolecules 2004; 37: 2544
      Crossref
    • 23b Hoare T, Pelton R. Langmuir 2004; 20: 2123
      CrossrefPubMed
  • 24 Sabadasch V, Wiehemeier L, Kottke T, Hellweg T. Soft Matter 2020; 16: 5422
    CrossrefPubMed
  • 25 Brändel T, Sabadasch V, Hannappel Y, Hellweg T. ACS Omega 2019; 4: 4636
    CrossrefPubMed
  • 26 Hoare T, McLean D. J. Phys. Chem. B 2006; 110: 20327
    CrossrefPubMed
  • 27 Pelton R. Adv. Colloid Interface Sci. 2000; 85: 1
    CrossrefPubMed
  • 28 Kroschwitz JI, Kirk RE, Othmer DF, Seidel A. Kirk-Othmer Encyclopedia of Chemical Technology . Wiley-Interscience; Hoboken: 2004
    Google Scholar
  • 29 Hoshino Y, Imamura K, Yue M, Inoue G, Miura Y. J. Am. Chem. Soc. 2012; 134: 18177
    CrossrefPubMed
    • 30a Hoare T, Pelton R. Curr. Opin. Colloid Interface Sci. 2008; 13: 413
      Crossref
    • 30b Kleinen J, Richtering W. Colloid Polym. Sci. 2011; 289: 739
      Crossref
  • 31 Friesen S, Hannappel Y, Kakorin S, Hellweg T. Gels 2021; 7: 42
    CrossrefPubMed
    • 32a Kratz K, Hellweg T, Eimer W. Colloids Surf., A 2000; 170: 137
      Crossref
    • 32b Karanastasis AA, Kenath GS, Andersen D, Fokas D, Ryu CY, Ullal CK. J. Colloid Interface Sci. 2020; 568: 264
      CrossrefPubMed
  • 33 Wrede O, Reimann Y, Lülsdorf S, Emmrich D, Schneider K, Schmid AJ, Zauser D, Hannappel Y, Beyer A, Schweins R, Gölzhäuser A, Hellweg T, Sottmann T. Sci. Rep. 2018; 13781
    CrossrefPubMed
    • 34a Gelissen AP. H, Scotti A, Turnhoff SK, Janssen C, Radulescu A, Pich A, Rudov AA, Potemkin II, Richtering W. Soft Matter 2018; 14: 4287
      CrossrefPubMed
    • 34b Annegarn M, Dirksen M, Hellweg T. Polymers 2021; 13: 827
      CrossrefPubMed
  • 35 Mourran A, Wu Y, Gumerov RA, Rudov AA, Potemkin II, Pich A, Möller M. Langmuir 2016; 32: 723
    CrossrefPubMed
  • 36 Hirano T, Nakamura K, Kamikubo T, Ishii S, Tani K, Mori T, Sato T. J. Polym. Sci., Part A: Polym. Chem. 2008; 46: 4575
    Crossref
  • 37 Rasband WS. ImageJ, version 1.52a 2021 . U. S. National Institutes of Health; Bethesda: 2021. https://imagej.nih.gov/ij/ (accessed April 3, 2022)
    Google Scholar
  • 38 Frisken BJ. Appl. Opt. 2001; 40: 4087
    CrossrefPubMed