Download PDF
Scheuermann, J.  et al.: 2024 Science of Synthesis, 2023/5: DNA-Encoded Libraries DOI: 10.1055/sos-SD-241-00055
DNA-Encoded Libraries

2.4 On-DNA C—X (X = N, O, P, S, Se) Bond Forming 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. D. ; 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

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

Heteroatoms are important components of drug molecules because they can not only modulate bioactivity through hydrogen bonding and dipole interactions, but also adjust drug-like properties. In view of this, the development of new methods for DNA-compatible carbon—heteroatom bond construction has received significant attention. This chapter summarizes the latest progress in on-DNA C—X (X = N, O, P, S, Se) bond construction methods.

Key words

DNA-encoded libraries - DNA-compatible reactions - carbon–heteroatom bonds - heteroatoms - synthesis
 
  • 1 Lu X, Roberts SE, Franklin GJ, Davie CP. Med. Chem. Commun. 2017; 8: 1614
  • 2 de Pedro Beato E, Priego J, Gironda-Martínez A, González F, Benavides J, Blas J, Martín-Ortega MD, Toledo MA, Ezquerra J, Torrado A. ACS Comb. Sci. 2019; 21: 69
  • 3 Xu H, Ma F, Wang N, Hou W, Xiong H, Lu F, Li J, Wang S, Ma P, Yang G, Lerner RA. Adv. Sci. (Weinheim, Ger.) 2019; 6: 1901 551
  • 4 Chen Y.-C, Faver JC, Ku AF, Miklossy G, Riehle K, Bohren KM, Ucisik MN, Matzuk MM, Yu Z, Simmons N. Bioconjugate Chem. 2020; 31: 770
  • 5 Graham JS, Hunter JH, Waring MJ. J. Org. Chem. 2021; 86: 17257
  • 6 Ruff Y, Berst F. Med. Chem. Commun. 2018; 9: 1188
  • 7 Ding Y, Chai J, Centrella PA, Gondo C, DeLorey JL, Clark MA. ACS Comb. Sci. 2018; 20: 251
  • 8 Wu Z, Graybill TL, Zeng X, Platchek M, Zhang J, Bodmer VQ, Wisnoski DD, Deng J, Coppo FT, Yao G, Tamburino A, Scavello G, Franklin GJ, Mataruse S, Bedard KL, Ding Y, Chai J, Summerfield J, Centrella PA, Messer JA, Pope AJ, Israel DI. ACS Comb. Sci. 2015; 17: 722
  • 9 Wang X, Liu J, Yan Z, Liu X, Liu S, Suo Y, Lu W, Yue J, Chen K, Jiang H, Zhao Y, Zheng M, Dai D, Lu X. Chem. Sci. 2021; 12: 2841
  • 10 Fan L, Davie CP. ChemBioChem 2017; 18: 843
  • 11 Cai K, Ran Y, Sun W, Gao S, Li J, Wan J, Liu G. Front. Chem. 2022; 10: 851674
  • 12 Franzini RM, Samain F, Abd Elrahman M, Mikutis G, Nauer A, Zimmermann M, Scheuermann J, Hall J, Neri D. Bioconjugate Chem. 2014; 25: 1453
  • 13 Flood DT, Asai S, Zhang X, Wang J, Yoon L, Adams ZC, Dillingham BC, Sanchez BB, Vantourout JC, Flanagan ME, Piotrowski DW, Richardson P, Green SA, Shenvi RA, Chen JS, Baran PS, Dawson PE. J. Am. Chem. Soc. 2019; 141: 9998
  • 14 Zhong S, Fang X, Wang Y, Zhang G, Li Y, Li Y. Org. Lett. 2022; 24: 1022
  • 15 Wang D.-Y, Wen X, Xiong C.-D, Zhao J.-N, Ding C.-Y, Meng Q, Zhou H, Wang C, Uchiyama M, Lu X.-J, Zhang A. iScience 2019; 15: 307
  • 16 Thomas B, Lu X, Birmingham WR, Huang K, Both P, Reyes Martinez JE, Young RJ, Davie CP, Flitsch SL. ChemBioChem 2017; 18: 858
  • 17 Flood DT, Zhang X, Fu X, Zhao Z, Asai S, Sanchez BB, Sturgell EJ, Vantourout JC, Richardson P, Flanagan ME, Piotrowski DW, Kölmel DK, Wan J, Tsai M.-H, Chen JS, Baran PS, Dawson PE. Angew. Chem. Int. Ed. 2020; 59: 7377
  • 18 Yang S, Zhao G, Gao Y, Sun Y, Zhang G, Fan X, Li Y, Li Y. Chem. Sci. 2022; 13: 2604
  • 19 Lin B, Lu W, Chen Z, Zhang Y, Duan Y, Lu X, Yan M, Zhang X. Org. Lett. 2021; 23: 7381
  • 20 Xu H, Wang Y, Dong H, Zhang Y, Gu Y, Zhang S, Meng Y, Li J, Shi XJ, Ji Q, Liu L, Ma P, Ma F, Yang G, Hou W. Angew. Chem. Int. Ed. 2022; 61: e202 206 516
  • 21 Xu H, Gu Y, Zhang S, Xiong H, Ma F, Lu F, Ji Q, Liu L, Ma P, Hou W, Yang G, Lerner RA. Angew. Chem. Int. Ed. 2020; 59: 13273
  • 22 Zhang Y, Chen W, Tan T, Gu Y, Zhang S, Li J, Wang Y, Hou W, Yang G, Ma P, Xu H. Chem. Commun. (Cambridge) 2021; 57: 4588
  • 23 Wen X, Duan Z, Liu J, Lu W, Lu X. Org. Lett. 2020; 22: 5721
  • 24 Barbaras D, Brozio J, Johannsen I, Allmendinger T. Org. Process Res. Dev. 2009; 13: 1068