Organic Letters
Letter
Complex Supramolecular Landscapes: Non-covalent Macrocyclization
Equilibria Examined by Fluorescence Resonance Energy Transfer.
Chem. Sci. 2018, 9, 7809−7821.
Oligonucleotides with Stacking of Phenyl-triazole Moieties in the
Major Groove. J. Org. Chem. 2011, 76, 6177−6187. (b) Seela, F.;
Budow, S.; Leonard, P. Oligonucleotides forming an i-motif: the pH-
dependent assembly of individual strands and branched structures
containing 2′-deoxy-5-propynylcytidine. Org. Biomol. Chem. 2007, 5,
1858−1872. (c) Song, Z.; Zhang, Q. Design, Synthesis, and
Incorporation of Fluorous 5-Methylcytosines into Oligonucleotides.
J. Org. Chem. 2011, 76, 10263−10268.
(22) Roychowdhury, A.; Illangkoon, H.; Hendrickson, C. L.; Benner,
S. A. 2‘-Deoxycytidines Carrying Amino and Thiol Functionality:
Synthesis and Incorporation by Vent (Exo−) Polymerase. Org. Lett.
2004, 6, 489−492.
́
(7) Bilbao, N.; Destoop, I.; De Feyter, S.; Gonzalez-Rodríguez, D.
Two-Dimensional Nanoporous Networks Formed by Liquid-to-Solid
Transfer of Hydrogen-Bonded Macrocycles Built from DNA Bases.
Angew. Chem., Int. Ed. 2016, 55, 659−663.
́
(8) (a) Mayoral, M. J.; Bilbao, N.; Gonzalez-Rodríguez, D.
Hydrogen-bonded Macrocyclic Supramolecular Systems in Solution
and onto Surfaces. ChemistryOpen 2016, 5, 10−32. (b) Aparicio, F.;
́
Mayoral, M. J.; Montoro-García, C.; Gonzalez-Rodríguez, D.
Guidelines for the Assembly of Hydrogen-bonded Macrocycles.
(23) (a) Dohno, C.; Shibata, T.; Okazaki, M.; Makishi, S.; Nakatani,
K. Amphiphilic DNA Duplex Stabilized by a Hydrophobic Zipper.
Eur. J. Org. Chem. 2012, 2012, 5317−5323. (b) Pujari, S. S.; Seela, F.
Parallel Stranded DNA Stabilized with Internal Sugar Cross-Links:
Synthesis and Click Ligation of Oligonucleotides Containing 2′-
Propargylated Isoguanosine. J. Org. Chem. 2013, 78, 8545−8561.
(24) Asakura, J.; Robins, M. J. Cerium(IV)-mediated halogenation at
C-5 of uracil derivatives. J. Org. Chem. 1990, 55, 4928−4933.
Chem. Commun. 2019, 55, 7277−7299.
́
́
(9) Vazquez-Gonzalez, V.; Mayoral, M. J.; Chamorro, R.; Hendrix,
́
M. M. R. M.; Voets, I. K.; Gonzalez-Rodríguez, D. Noncovalent
Synthesis of Self-assembled Nanotubes through Decoupled Hier-
archical Cooperative Processes. J. Am. Chem. Soc. 2019, 141, 16432−
16438.
́
(10) (a) Chinchilla, R.; Najera, C. Recent advances in Sonogashira
reactions. Chem. Soc. Rev. 2011, 40, 5084−5121. (b) Agrofoglio, L. A.;
Gillaizeau, I.; Saito, Y. Palladium-Assisted Routes to Nucleosides.
Chem. Rev. 2003, 103, 1875−1916. (c) Bielski, R.; Witczak, Z. J.
Strategies for Coupling Molecular Units if Subsequent Decoupling Is
Required. Chem. Rev. 2013, 113, 2205−2243.
̈
(25) (a) Borjesson, K.; Wiberg, J.; El-Sagheer, A. H.; Ljungdahl, T.;
́
Mårtensson, J.; Brown, T.; Norden, B.; Albinsson, B. Functionalized
Nanostructures: Redox-Active Porphyrin Anchors for Supramolecular
DNA Assemblies. ACS Nano 2010, 4, 5037−5046. (b) Tashiro, R.;
Iwamoto, M.; Morinaga, H.; Emura, T.; Hidaka, K.; Endo, M.;
Sugiyama, H. Linking two DNA duplexes with a rigid linker for DNA
nanotechnology. Nucleic Acids Res. 2015, 43, 6692−6700. (c) Ga-
ballah, S. T.; Netzel, T. L. Synthesis of 5-(Pyridinyl and
Pyridiniumyl)-20-Deoxyuridine Nucleosides: Reversible Electron
Traps for DNA. Nucleosides, Nucleotides Nucleic Acids 2002, 21,
681−694. (d) Segal, M.; Yavin, E.; Kafri, P.; Shav-Tal, Y.; Fischer, B.
Detection of mRNA of the Cyclin D1 Breast Cancer Marker by a
Novel Duplex-DNA Probe. J. Med. Chem. 2013, 56, 4860−4869.
(11) Wei, X. Coupling activators for the oligonucleotide synthesis
via phosphoramidite approach. Tetrahedron 2013, 69, 3615−3637.
́
́
́
(12) (a) Bilbao, N.; Vazquez-Gonzalez, V.; Aranda, M. T.; Gonzalez-
Rodríguez, D. Synthesis of 5-/8-Halogenated or Ethynylated Lip-
ophilic Nucleobases as Potential Synthetic Intermediates for Supra-
molecular Chemistry. Eur. J. Org. Chem. 2015, 2015, 7160−7175.
́
́
(b) Camacho-García, J.; Montoro-García, C.; Lopez-Perez, A. M.;
́
́
Bilbao, N.; Romero-Perez, S.; Gonzalez-Rodríguez, D. Synthesis and
Complementary Self-association of Novel Lipophilic π-Conjugated
Nucleoside Oligomers. Org. Biomol. Chem. 2015, 13, 4506−4513.
(13) Sun, F. P.; Darbre, T. Synthesis and Irradiation of Vitamin-B12-
Derived Complexes Incorporating Peripheral G·C Base Pairs. Helv.
Chim. Acta 2002, 85, 3002−3018.
(14) Kaloudis, P.; D’Angelantonio, M.; Guerra, M.; Gimisis, T.;
Mulazzani, Q. G.; Chatgilialoglu, C. One-electron reduction of 8-
bromo-2-aminoadenosine: Chemical radiation and DFT studies of the
mechanism. J. Phys. Chem. B 2008, 112, 5209−5217.
(15) (a) Garrett, E. R.; Mehta, P. J. Solvolysis of adenine
nucleosides. I. Effects of sugars and adenine substituents on acid
solvolyses. J. Am. Chem. Soc. 1972, 94, 8532−8541. (b) Rios, A. C.;
Yu, H. T.; Tor, Y. Hydrolytic fitness of N-glycosyl bonds: comparing
the deglycosylation kinetics of modified, alternative, and native
nucleosides. J. Phys. Org. Chem. 2015, 28, 173−180.
(16) Kaiya, T.; Tanaka, H.; Kohda, K. Formation of 2’-deoxy-2-
nitroadenosines by reaction of 2’-deoxyadenosines with copper(II)
Nitrate/acetic anhydride. Nucleosides, Nucleotides Nucleic Acids 2002,
21, 427−433.
(17) Rodenko, B.; Wanner, M. J.; Alkhaldi, A. A. M.; Ebiloma, G. U.;
Barnes, R. L.; Kaiser, M.; Brun, R.; McCulloch, R.; Koomen, G.; de
Koning, H. P. Targeting the Parasite’s DNA with Methyltriazenyl
Purine Analogs Is a Safe, Selective, and Efficacious Antitrypanosomal
Strategy. Antimicrob. Agents Chemother. 2015, 59, 6708−6716.
(18) Rodriguez, A. A.; Cedillo, I.; Mowery, B. P.; Gaus, H. J.;
Krishnamoorthy, S. S.; McPherson, A. K. Formation of the N2-acetyl-
2,6-diaminopurine oligonucleotide impurity caused by acetyl capping.
Bioorg. Med. Chem. Lett. 2014, 24, 3243−3246.
(19) Munzel, M.; Globisch, D.; Trindler, C.; Carell, T. Efficient
̈
Synthesis of 5-Hydroxymethylcytosine Containing DNA. Org. Lett.
2010, 12, 5671−5673.
(20) Andersen, N. K.; Dossing, H.; Jensen, F.; Vester, B.; Nielsen, P.
Duplex and Triplex Formation of Mixed Pyrimidine Oligonucleotides
with Stacking of Phenyl-triazole Moieties in the Major Groove. J. Org.
Chem. 2011, 76, 6177−6187.
(21) (a) Andersen, N. K.; Dossing, H.; Jensen, F.; Vester, B.;
Nielsen, P. Duplex and Triplex Formation of Mixed Pyrimidine
E
Org. Lett. XXXX, XXX, XXX−XXX