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Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7
Graphical Abstract
Figure 1: a) Angles and unit vectors used to define the relative orientations of the donor and acceptor trans...
Figure 2: Notable recent examples of fluorescent base analogues. For cnA and dnA the attachment point to the ...
Scheme 1: Synthesis of the tricyclic cytosine aromatic core [39]. (a) Ethylene glycol, K2CO3, 120 °C, 1 h, 40%; (...
Scheme 2: Synthesis of protected tC and tCO deoxyribose phosphonates [41]. (a) Ac2O, pyridine, rt; (b) 2-mesityle...
Scheme 3: Synthesis of protected tCnitro deoxyribose phosphoramidite [14]. a) aq NaOH, 24 h, reflux; b) EtOH, HCl...
Scheme 4: Improved synthesis of tC and tC derivatives, where R = H, 7-MeO or 8-MeO [47]. a) H2NNH2 followed by H2O...
Scheme 5: Improved synthesis of tCO derivatives [47]. a) Ac2O, pyridine, 16 h, rt, 85%; b) PPh3, CCl4, DCM, 5 h, ...
Scheme 6: Synthesis of protected tCO ribose phosphoramidite [50]. a) MesSO2Cl, DIPEA, MeCN, 4 h, rt; b) 2-aminoph...
Scheme 7: Synthesis of protected deoxyribose qA [51]. a) N-(tert-Butoxycarbonyl)-2-(trimethylstannyl)aniline, (Ph3...
Scheme 8: Synthesis of protected deoxyribose qA for DNA SPS [53]. a) AcCl, MeOH, rt, 40 min; b) p-toluoyl chlorid...
Scheme 9: Synthesis of qA derivatives. a) EtI, Cs2CO3, DMF, 4 h, rt, 90%; b) HBPin, Pd(PPh3)4, Et3N, 1,4-diox...
Scheme 10: Synthesis of quadracyclic adenine base–base FRET pair. a) HCHO, NaOH, MeCN, H2O, 50 °C, 1 h; b) TBD...
Figure 3: Absorption and emission of tC (dashed line) and tCO (solid line) in dsDNA. The absorption below 300...
Figure 4: Spectral overlap between the emission of qAN1 (cyan) and the absorption of qAnitro (black) in dsDNA...
Figure 5: Example of typical FRET efficiency as a function of number of base pairs separating the donor and a...
Figure 6: FRET efficiency as a function of number of base pairs separating the donor (qAN1) and acceptor (qAn...