PDF herunterladen
2.9 On-DNA Functional-Group Transformations
Buch
Herausgeber: Scheuermann, J. ; Li, 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;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
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
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- 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
- 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
- 8 A Handbook for DNA-Encoded Chemistry: Theory and Applications for Exploring Chemical Space and Drug Discovery. Goodnow Jr RA. Wiley; Hoboken, NJ 2014
- 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
- 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
- 13 Bigatti M, Dal Corso A, Vanetti S, Cazzamalli S, Rieder U, Scheuermann J, Neri D, Sladojevich F. ChemMedChem 2017; 12: 1748
- 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 corrigendum: Bioconjugate Chem. 2016; 27: 2580
- 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
- 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
- 22 Li Y, De Luca R, Cazzamalli S, Pretto F, Bajic D, Scheuermann J, Neri D. Nat. Chem. 2018; 10: 441
- 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
- 25 Ruff Y, Martinez R, Pellé X, Nimsgern P, Fille P, Ratnikov M, Berst F. ACS Comb. Sci. 2020; 22: 120
- 26 Monty OBC, Nyshadham P, Bohren KM, Palaniappan M, Matzuk MM, Young DW, Simmons N. ACS Comb. Sci. 2020; 22: 80
- 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
- 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
- 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
- 34 Du H.-C, Simmons N, Faver JC, Yu Z, Palaniappan M, Riehle K, Matzuk MM. Org. Lett. 2019; 21: 2194
- 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
- 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
- 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
- 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
- 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
- 48 Thomas B, Lu X, Birmingham WR, Huang K, Both P, Reyes Martinez JE, Young RJ, Davie CP, Flitsch SL. ChemBioChem 2017; 18: 858
- 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
- 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
- 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
- 52 Gartner ZJ, Tse BN, Grubina R, Doyon JB, Snyder TM, Liu DR. Science (Washington, D. C.) 2004; 305: 1601
- 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
- 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
- 59 Klika Škopić M, Willems S, Wagner B, Schieven J, Krause N, Brunschweiger A. Org. Biomol. Chem. 2017; 15: 8648
- 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