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Scheuermann, J.  et al.: 2024 Science of Synthesis, 2023/5: DNA-Encoded Libraries DOI: 10.1055/sos-SD-241-00134
DNA-Encoded Libraries

2.9 On-DNA Functional-Group Transformations

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Buch

Herausgeber: Scheuermann, J. ; Li, Y. 

Autoren: 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. 

Titel: DNA-Encoded Libraries

Print ISBN: 9783132455221; Online ISBN: 9783132437357; Buch-DOI: 10.1055/b000000342

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

Fachgebiete: Organische Chemie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: 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.

Typ: Mehrbändiges Werk

Auch verfügbar auf
 


Abstract

DNA-encoded libraries of small molecules typically access diverse chemical space via combinatorial coupling of building blocks and cores already bearing the requisite functional groups for the intended on-DNA synthetic sequence. However, on-DNA functional group transformations, wherein an on-DNA functional group is altered without the incorporation of a new diversity element, is a supplemental approach to expand the scope of on-DNA synthesis. This chapter reviews key on-DNA functional-group transformations for strategies such as the utilization of on-DNA protecting groups to enhance orthogonality, the in situ generation of commercially-rare or unstable on-DNA synthetic intermediates to enable extension of valuable core collections to alternative synthetic pathways, the employment of temporary functional groups as handles to regulate on-DNA chemical reactivity, and the encoding of specific functional groups into final library molecules.

Schlüsselwörter

DNA-encoded libraries - DNA-compatible reactions - protecting groups - multistep synthesis - functional-group interconversion
 
  • 1 Zhang Y, Clark MA. Bioorg. Med. Chem. 2021; 41: 116189
    PubMed
  • 2 Martín A, Nicolaou CA, Toledo MA. Commun. Chem. 2020; 3: 127
    PubMed
  • 3 Zhu H, Flanagan ME, Stanton RV. J. Chem. Inf. Model. 2019; 59: 4645
    PubMed
  • 4 Franzini RM, Biendl S, Mikutis G, Samain F, Scheuermann J, Neri D. ACS Comb. Sci. 2015; 17: 393
    PubMed
  • 5 Ratnayake AS, Flanagan ME, Foley TL, Hultgren SL, Bellenger J, Montgomery JI, Lall MS, Liu B, Ryder T, Kölmel DK, Shavnya A, Feng X, Lefker B, Byrnes LJ, Sahasrabudhe PV, Farley KA, Chen S, Wan J. Bioorg. Med. Chem. 2021; 41: 116205
    PubMed
  • 6 Madsen D, Azevedo C, Micco I, Petersen LK, Hansen NJV, In: Progress in Medicinal Chemistry Witty DR, Cox B. Elsevier Amsterdam 2020; 59. 181
  • 7 Yang G, He D, Zhu Y, Zhu W, Tan Y, Long X, Wan J, Shi Z, Schuman D, Chheda P, Simmons N, Liu G. Bioconjugate Chem. 2021; 32: 667
    PubMed
  • 8 A Handbook for DNA-Encoded Chemistry: Theory and Applications for Exploring Chemical Space and Drug Discovery. Goodnow Jr RA. Wiley; Hoboken, NJ 2014
    CrossrefGoogle Scholar
  • 9 Li J.-Y, Miklossy G, Modukuri RK, Bohren KM, Yu Z, Palaniappan M, Faver JC, Riehle K, Matzuk MM, Simmons N. Bioconjugate Chem. 2019; 30: 2209
    PubMed
  • 10 Malone ML, Paegel BM. ACS Comb. Sci. 2016; 18: 182
    PubMed
  • 11 Deng H, OʼKeefe H, Davie CP, Lind KE, Acharya RA, Franklin GJ, Larkin J, Matico R, Neeb M, Thompson MM, Lohr T, Gross JW, Centrella PA, OʼDonovan GK, Bedard KL(Sargent), van Vloten K, Mataruse S, Skinner SR, Belyanskaya SL, Carpenter TY, Shearer TW, Clark MA, Cuozzo JW, Arico-Muendel CC, Morgan BA. J. Med. Chem. 2012; 55: 7061
    PubMed
  • 12 Hejesen C, Petersen LK, Hansen NJV, Gothelf KV. Org. Biomol. Chem. 2013; 11: 2493
    PubMed
  • 13 Bigatti M, Dal Corso A, Vanetti S, Cazzamalli S, Rieder U, Scheuermann J, Neri D, Sladojevich F. ChemMedChem 2017; 12: 1748
    PubMed
  • 14 George N, Ofori S, Parkin S, Awuah SG. RSC Adv. 2020; 10: 24017
    PubMed
  • 15 Wang G, Li C, Li J, Jia X. Tetrahedron Lett. 2009; 50: 1438
  • 16 Satz AL, Cai J, Chen Y, Goodnow R, Gruber F, Kowalczyk A, Petersen A, Naderi-Oboodi G, Orzechowski L, Strebel Q. Bioconjugate Chem. 2015; 26: 1623 Bioconjugate Chem. 2016; 27: 2580
    PubMed
  • 17 Gerry CJ, Wawer MJ, Clemons PA, Schreiber SL. J. Am. Chem. Soc. 2019; 141: 10225
    PubMed
  • 18 Klika Škopić M, Gramse C, Oliva R, Pospich S, Neukirch L, Manisegaran M, Raunser S, Winter R, Weberskirch R, Brunschweiger A. Chem.–Eur. J. 2021; 27: 10048
    PubMed
  • 19 Wuts PGM, Northuis JM. Tetrahedron Lett. 1998; 39: 3889
  • 20 Chamakuri S, Chung M.-K, Samuel ELG, Tran KA, Chen Y.-C, Nyshadham P, Santini C, Matzuk MM, Young DW. Bioorg. Med. Chem. 2021; 48: 116387
    PubMed
  • 21 Stress CJ, Sauter B, Schneider LA, Sharpe T, Gillingham D. Angew. Chem. Int. Ed. 2019; 58: 9570
    PubMed
  • 22 Li Y, De Luca R, Cazzamalli S, Pretto F, Bajic D, Scheuermann J, Neri D. Nat. Chem. 2018; 10: 441
    PubMed
  • 23 Priego J, de Pedro Beato E, Benavides J, Gironda-Martínez A, González F, Blas J, Martín-Ortega MD, Rama-Garda R, Ezquerra J, Toledo MA, Torrado A. Bioconjugate Chem. 2021; 32: 88
    PubMed
  • 24 Roloff A, Seitz O. Chem. Sci. 2013; 4: 432
  • 25 Ruff Y, Martinez R, Pellé X, Nimsgern P, Fille P, Ratnikov M, Berst F. ACS Comb. Sci. 2020; 22: 120
    PubMed
  • 26 Monty OBC, Nyshadham P, Bohren KM, Palaniappan M, Matzuk MM, Young DW, Simmons N. ACS Comb. Sci. 2020; 22: 80
    PubMed
  • 27 Stanway-Gordon HA, Graham JS, Waring MJ. Angew. Chem. Int. Ed. 2022; 61: e202 111 927
  • 28 Price AK, Paegel BM. ACS Comb. Sci. 2020; 22: 649
    PubMed
  • 29 Franch T, Lundorf MD, Jacobsen SN, Olsen EK, Andersen AL, Holtmann A, Hansen AH, Sorensen AM, Goldbech A, de Leon D, Kaldor DK, Slok FA, Husemoen GN, Dolberg J, Jensen KB, Pedersen L, Norregaard-Madsen M, Godskesen MA, Glad SS, Neve S, Thisted T, Kronborg TTA, Sams CK, Felding J, Freskgard P.-O, Gouliaev AH, Pedersen H. US 2009 0 264 300 A1, 2009
    PubMed
  • 30 Favalli N, Biendl S, Hartmann M, Piazzi J, Sladojevich F, Gräslund S, Brown PJ, Näreoja K, Schüler H, Scheuermann J, Franzini R, Neri D. ChemMedChem 2018; 13: 1303
    PubMed
  • 31 Qu Y, Liu S, Wen H, Xu Y, An Y, Li K, Ni M, Shen Y, Shi X, Su W, Cui W, Kuai L, Satz AL, Yang H, Lu X, Peng X. Biochem. Biophys. Res. Commun. 2020; 533: 209
    PubMed
  • 32 Chheda PR, Simmons N, Schuman DP, Shi Z. Org. Lett. 2022; 24: 3401
    PubMed
  • 33 Ding Y, Chai J, Centrella PA, Gondo C, DeLorey JL, Clark MA. ACS Comb. Sci. 2018; 20: 251
    PubMed
  • 34 Du H.-C, Simmons N, Faver JC, Yu Z, Palaniappan M, Riehle K, Matzuk MM. Org. Lett. 2019; 21: 2194
    PubMed
  • 35 Du H.-C, Huang H. Bioconjugate Chem. 2017; 28: 2575
    PubMed
  • 36 Sakurai K, Snyder TM, Liu DR. J. Am. Chem. Soc. 2005; 127: 1660
    PubMed
  • 37 Wrenn SJ, Weisinger RM, Halpin DR, Harbury PB. J. Am. Chem. Soc. 2007; 129: 13137
    PubMed
  • 38 Chen Y, Kamlet AS, Steinman JB, Liu DR. Nat. Chem. 2011; 3: 146
    PubMed
  • 39 Estévez AM, Gruber F, Satz AL, Martin RE, Wessel HP. Tetrahedron: Asymmetry 2017; 28: 837
  • 40 Dawadi S, Simmons N, Miklossy G, Bohren KM, Faver JC, Ucisik MN, Nyshadham P, Yu Z, Matzuk MM. Proc. Natl. Acad. Sci. U. S. A. 2020; 117: 16782
    PubMed
  • 41 Ma F, Li J, Zhang S, Gu Y, Tan T, Chen W, Wang S, Ma P, Xu H, Yang G, Lerner RA. Chem.–Eur. J. 2021; 27: 8214
    PubMed
  • 42 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
    PubMed
  • 43 Denton KE, Krusemark CJ. Med. Chem. Commun. 2016; 7: 2020
    PubMed
  • 44 Korsager S, Taaning RH, Skrydstrup T. J. Am. Chem. Soc. 2013; 135: 2891
    PubMed
  • 45 Sang R, Kucmierczyk P, Dühren R, Razzaq R, Dong K, Liu J, Franke R, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2019; 58: 14365
    PubMed
  • 46 Liu W, Huang W, Lin Q, Tsai M.-H, Zhang R, Fan L, Scott JD, Liu G, Wan J. Bioorg. Med. Chem. 2021; 38: 116118
    PubMed
  • 47 Paciaroni NG, Ndungu JM, Kodadek T. Chem. Commun. (Cambridge) 2020; 56: 4656
    PubMed
  • 48 Thomas B, Lu X, Birmingham WR, Huang K, Both P, Reyes Martinez JE, Young RJ, Davie CP, Flitsch SL. ChemBioChem 2017; 18: 858
    PubMed
  • 49 Klika Škopić M, Götte K, Gramse C, Dieter M, Pospich S, Raunser S, Weberskirch R, Brunschweiger A. J. Am. Chem. Soc. 2019; 141: 10546
    PubMed
  • 50 Litovchick A, Dumelin CE, Habeshian S, Gikunju D, Guié M.-A, Centrella P, Zhang Y, Sigel EA, Cuozzo JW, Keefe AD, Clark MA. Sci. Rep. 2015; 5: 10916
    PubMed
  • 51 Li K, Qu Y, An Y, Breinlinger E, Webster MP, Wen H, Ding D, Zhao M, Shi X, Wang J, Su W, Cui W, Satz AL, Yang H, Kuai L, Little A, Peng X. Bioconjugate Chem. 2020; 31: 2092
    PubMed
  • 52 Gartner ZJ, Tse BN, Grubina R, Doyon JB, Snyder TM, Liu DR. Science (Washington, D. C.) 2004; 305: 1601
    PubMed
  • 53 Gartner ZJ, Kanan MW, Liu DR. J. Am. Chem. Soc. 2002; 124: 10304
    PubMed
  • 54 Gouliaev AH, Franch T, Godskesen MA, Jensen KB. US 20 130 281 324A1, 2013
    PubMed
  • 55 Fan Z, Zhao S, Liu T, Shen P.-X, Cui Z.-N, Zhuang Z, Shao Q, Chen JS, Ratnayake AS, Flanagan ME, Kölmel DK, Piotrowski DW, Richardson P, Yu J.-Q. Chem. Sci. 2020; 11: 12282
    PubMed
  • 56 Wen X, Duan Z, Liu J, Lu W, Lu X. Org. Lett. 2020; 22: 5721
    PubMed
  • 57 Wen H, Ge R, Qu Y, Sun J, Shi X, Cui W, Yan H, Zhang Q, An Y, Su W, Yang H, Kuai L, Satz AL, Peng X. Org. Lett. 2020; 22: 9484
    PubMed
  • 58 Fan L, Davie CP. ChemBioChem 2017; 18: 843
    PubMed
  • 59 Klika Škopić M, Willems S, Wagner B, Schieven J, Krause N, Brunschweiger A. Org. Biomol. Chem. 2017; 15: 8648
    PubMed
  • 60 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
    PubMed
  • 61 Halpin DR, Lee JA, Wrenn SJ, Harbury PB. PLoS Biol. 2004; 2: e175
    PubMed
  • 62 Pham MV, Bergeron-Brlek M, Heinis C. ChemBioChem 2020; 21: 543
    PubMed
  • 63 Zhang J, Li X, Wei H, Li Y, Zhang G, Li Y. Org. Lett. 2021; 23: 8429
    PubMed
  • 64 Ma F, Li J, Zhang S, Gu Y, Tan T, Chen W, Wang S, Xu H, Yang G, Lerner RA. ACS Catal. 2022; 12: 1639
  • 65 Qi J, Liu S, Seydimemet M, Wang X, Lu X. Bioconjugate Chem. 2021; 32: 2290
    PubMed
  • 66 Liu S, Qi J, Lu W, Wang X, Lu X. Org. Lett. 2021; 23: 908 Org. Lett. 2022; 24: 4716
    PubMed
  • 67 Du H.-C, Bangs MC, Simmons N, Matzuk MM. Bioconjugate Chem. 2019; 30: 1304
    PubMed
  • 68 Gironda-Martínez A, Neri D, Samain F, Donckele EJ. Org. Lett. 2019; 21: 9555
    PubMed
  • 69 Ede S, Schenk M, Bierer D, Weinmann H, Graham K. Molecules 2021; 26: 1790
    PubMed
  • 70 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