- The DNA-stabilising nucleoside 7-iodo-2′-deoxytubercidin: Its structure in the solid state and in solution
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The crystal structure of 7-iodo-2′-deoxytubercidin 2 has been determined and was compared with those of 2′-deoxytubercidin 3 and 2′-deoxyadenosine 4. The bulky 7-iodo substituent lies 13.2 pm below and the nitrogen of the 6-amino group 5.5 pm above the 7-deazapurine plane. The puckering of compound 2 is 3′E while compound 3 shows a 2′T3′ sugar pucker. The conformation in aqueous solution, determined by 1H NMR spectroscopy, is only slightly different, showing a 2′E conformation. The glycosylic bond torsion angle is anti in all cases.
- Seela, Frank,Zulauf, Matthias,Rosemeyer, Helmut,Reuter, Hans
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Read Online
- Synthesis and photophysical evaluation of new fluorescent 7-arylethynyl-7-deazaadenosine analogs
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Three new fluorescent 7-deaza-2′-deoxyadenosine analogs were synthesized via the Sonogashira cross-coupling reaction of 7-iodo-7-deaza-2′-deoxyadenosine with 1-ethynylpyrene, 2-ethynyl-6-methoxynaphthalene, and 9-ethynylphenanthrene. The spectral properties of these analogs were evaluated in dioxane, EtOH, and H2O to determine their potential for use as environmentally sensitive fluorescent probes. All three analogs displayed large solvatofluorochromicity in H2O, relative to their emission wavelengths in dioxane or EtOH. Moreover, all three analogs exhibited microenvironmental sensitivity of their fluorescence emission intensity, being moderate to high quantum yields in dioxane and EtOH and significantly lower in H2O. Various attempts to perform domino cross-coupling and annuation reactions on 7-deaza-7-alkynyladenine derivatives to form a new fused tricyclic adenine analog were unsuccessful.
- Matarazzo, Augusto,Brow, Justin,Hudson, Robert H.E.
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p. 1093 - 1100
(2018/11/25)
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- 4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
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Provided is 4'-substituted nucleoside derivatives of Formula I and their use in the inhibition of HIV reverse transcriptase, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS and/or ARC.
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Page/Page column 54; 55; 56
(2015/12/08)
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- Method and reagent for gene sequence analysis
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Provided is a nucleic acid substrate which has nucleic acid substrate characteristics equivalent to those of dATP, has a low substrate specificity for luciferase, exerts no negative effect on enzymatic reactions such as a complementary-strand synthesis, and therefore is particularly suitable for the pyrosequencing method. As a nucleic acid substrate complementary to nucleotide T, a 7-substituted deoxyribonucleotide triphosphate whose 7-position of a purine group is modified by a substituent is used as a substitute for a nucleotide α-thiotriphosphate analog.
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Page/Page column 16
(2014/10/16)
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- Palladium-catalyzed cross coupling of 7-iodo-2'-deoxytubercidin with terminal alkynes
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The 7-alkynyl-2'-deoxytubercidins (7-deaza-2'-deoxyadenosines) 7-17 have been prepared by the Pd(0)/Cu(I)-catalyzed cross coupling of 7-iodo-2'-deoxytubercidin (2d) with terminal alkynes. The coupling products include 17α-ethynyltestosterone and 17α-ethynylestradiol derivatives (16, 17).
- Seela, Frank,Zulauf, Matthias
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p. 726 - 730
(2007/10/03)
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