Download PDF
Scheuermann, J.  et al.: 2024 Science of Synthesis, 2023/5: DNA-Encoded Libraries DOI: 10.1055/sos-SD-241-00126
DNA-Encoded Libraries

2.8 DNA-Encoded Isocyanide Multicomponent Reactions

More Information

Book

Editors: Scheuermann, J. ; Li, Y. 

Authors: Barluenga, S. ; Bassi, G. ; Brunschweiger, A. ; Cai, B. ; Cazzamalli, S. ; Chheda, P. ; Cui, M. ; Cui, W. ; Fang, X. ; Farrera-Soler, L. ; Favalli, N. ; Feng, J.; Foley, T. L. ; Franzini, R. M. ; Georgiev, T. ; Gillingham, D. ; Gloger, A. ; Graham, J. S. ; Granados, A. ; Heiden, S.; Hou, W. ; Huang, Y. ; Keefe, A. D. ; Krusemark, C. J. ; Li, X. ; Li, Y. ; Lin, W. ; Litovchick, A.; Liu, G. ; Lu, X. ; Lucaroni, L. ; Ma, P. ; Migliorini, F. ; Molander, G. A. ; Neri, D. ; Nie, Q. ; Oehler, S. ; Prati, L. ; Puglioli, S. ; Reddavide, F. V. ; Satz, A. L. ; Sauter, B. ; Scheuermann, J. ; Schuman, D.; Simmons, N. ; Stanway-Gordon, H. A. ; Su, W. ; Sun, J. ; Thompson, M.; Vummidi, B. R.; Wang, X. ; Wang, Y. ; Wang, Z. ; Waring, M. J. ; Willems, S.; Winssinger, N. ; Xia, B. ; Xiong, F. ; Xu, H. ; Xu, L. ; Yang, G. ; Zhang, G. ; Zhang, Y. ; Zhou, Y. 

Title: DNA-Encoded Libraries

Print ISBN: 9783132455221; Online ISBN: 9783132437357; Book DOI: 10.1055/b000000342

1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

Isocyanide multicomponent reactions (IMCRs) provide access to a plethora of molecular architectures. Four IMCRs have been translated to a DNA-barcoding strategy involving the use of chemically stabilized DNA barcodes coupled to a controlled-pore glass solid support. These are the Ugi reaction, the Gröbke–Blackburn–Bienaymé reaction, the Ugi-azide reaction, and the Ugi–aza-Wittig reaction. The reactions were all performed using DNA-tagged aldehydes, and provide diverse scaffolds. The DNA used in this barcoding strategy was composed of three nucleobases: thymine, cytosine, and 7-deaza-adenine, as a more depurination-resistant congener of adenine.

Key words

DNA-encoded libraries - DNA-compatible reactions - controlled-pore glass - Gröbke–Blackburn–Bienaymé reaction - multicomponent reactions - isocyanides - solid phase - scaffold diversity - Ugi reaction - Ugi-azide reaction - Ugi–aza-Wittig reaction
 
  • 7 Kunig VBK, Potowski M, Akbarzadeh M, Klika Škopić M, dos Santos Smith D, Arendt L, Dormuth I, Adihou H, Andlovic B, Karatas H, Shaabani S, Zarganes-Tzitzikas T, Neochoritis CG, Zhang R, Groves M, Guéret SM, Ottmann C, Rahnenführer J, Fried R, Dömling A, Brunschweiger A. Angew. Chem. Int. Ed. 2020; 59: 20338
    CrossrefPubMedSearch in Google Scholar
  • 9 Franzini RM, Ekblad T, Zhong N, Wichert M, Decurtins W, Nauer A, Zimmermann M, Samain F, Scheuermann J, Brown PJ, Hall J, Gräslund S, Schüler H, Neri D. Angew. Chem. Int. Ed. 2015; 54: 3927
    CrossrefPubMedSearch in Google Scholar