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Conformation of two 4'-thio-2'-deoxynucleoside analogs studied by 5000-MHz proton NMR spectroscopy and x-ray crystallography.

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    Conformation of two 4'-thio-2'-deoxynucleoside analogs studied by 5000-MHz proton NMR spectroscopy and x-ray crystallography.
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 1992, 114, 25, 9936–9943
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    https://doi.org/10.1021/ja00051a028
    Published December 1, 1992
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    2. Matthew Maddess John McIntosh Wonsuk Chang . Discovery and Chemical Development of Uvelostinag (MK-1454): A Therapeutic Cyclic Dinucleotide Agonist of the Stimulator of Interferon Gene. , 1-94. https://doi.org/10.1021/bk-2022-1423.ch001
    3. Hashem A. Taha, Michele R. Richards, and Todd L. Lowary . Conformational Analysis of Furanoside-Containing Mono- and Oligosaccharides. Chemical Reviews 2013, 113 (3) , 1851-1876. https://doi.org/10.1021/cr300249c
    4. Jarrod W. Johnson, Darryl P. Evanoff, Marc E. Savard, Gerald Lange, Timothy R. Ramadhar, Abdeljalil Assoud, Nicholas J. Taylor and Gary I. Dmitrienko. Cyclobutanone Mimics of Penicillins: Effects of Substitution on Conformation and Hemiketal Stability. The Journal of Organic Chemistry 2008, 73 (18) , 6970-6982. https://doi.org/10.1021/jo801274m
    5. Joseph J. Barchi, Jr., Rajeshri G. Karki, Marc C. Nicklaus, Maqbool A. Siddiqui, Clifford George, Igor A. Mikhailopulo and Victor E. Marquez. Comprehensive Structural Studies of 2′,3′-Difluorinated Nucleosides: Comparison of Theory, Solution, and Solid State. Journal of the American Chemical Society 2008, 130 (28) , 9048-9057. https://doi.org/10.1021/ja800964g
    6. Jonathan K. Watts, Blair D. Johnston, Kumarasamy Jayakanthan, Alexander S. Wahba, B. Mario Pinto and Masad J. Damha. Synthesis and Biophysical Characterization of Oligonucleotides Containing a 4′-Selenonucleotide. Journal of the American Chemical Society 2008, 130 (27) , 8578-8579. https://doi.org/10.1021/ja802205u
    7. Gourav Das, S. Harikrishna, Kiran R. Gore. Influence of Sugar Modifications on the Nucleoside Conformation and Oligonucleotide Stability: A Critical Review. The Chemical Record 2022, 22 (12) https://doi.org/10.1002/tcr.202200174
    8. Mary K. Yates, Katherine L. Seley-Radtke. The evolution of antiviral nucleoside analogues: A review for chemists and non-chemists. Part II: Complex modifications to the nucleoside scaffold. Antiviral Research 2019, 162 , 5-21. https://doi.org/10.1016/j.antiviral.2018.11.016
    9. Marina Evich, Alexander M. Spring-Connell, Markus W. Germann. Impact of modified ribose sugars on nucleic acid conformation and function. Heterocyclic Communications 2017, 23 (3) , 155-165. https://doi.org/10.1515/hc-2017-0056
    10. Didier LeNouen, Albert Defoin, Jean-Bernard Behr. Determination of the Relative Configuration and Conformational Analysis of Five-membered N -Acyl-Iminosugars by Relevant 3 J Coupling Constants.. ChemistrySelect 2016, 1 (6) , 1256-1267. https://doi.org/10.1002/slct.201600287
    11. N. Tarashima, T. Sumitomo, H. Ando, K. Furukawa, T. Ishida, N. Minakawa. Synthesis of DNA fragments containing 2′-deoxy-4′-selenonucleoside units using DNA polymerases: comparison of dNTPs with O, S and Se at the 4′-position in replication. Organic & Biomolecular Chemistry 2015, 13 (25) , 6949-6952. https://doi.org/10.1039/C5OB00941C
    12. Ryogo Minamimoto, Jun Toyohara, Ayako Seike, Hideyuki Ito, Hisako Endo, Miyako Morooka, Kazuhiko Nakajima, Takuya Mitsumoto, Kimiteru Ito, Momoko Okasaki, Kiichi Ishiwata, Kazuo Kubota. 4′-[Methyl- 11 C]-Thiothymidine PET/CT for Proliferation Imaging in Non–Small Cell Lung Cancer. Journal of Nuclear Medicine 2012, 53 (2) , 199-206. https://doi.org/10.2967/jnumed.111.095539
    13. Feng Zheng, Lin Fu, Renxiao Wang, Feng-Ling Qing. Synthesis and conformational analysis of d -2′-deoxy-2′,2′-difluoro-4′-dihydro-4′-thionucleosides. Org. Biomol. Chem. 2010, 8 (1) , 163-170. https://doi.org/10.1039/B914679B
    14. Pieter MS Hendrickx, José C Martins. A user-friendly Matlab program and GUI for the pseudorotation analysis of saturated five-membered ring systems based on scalar coupling constants. Chemistry Central Journal 2008, 2 (1) https://doi.org/10.1186/1752-153X-2-20
    15. Kumarasamy Jayakanthan, Blair D. Johnston, B. Mario Pinto. Stereoselective synthesis of 4′-selenonucleosides using the Pummerer glycosylation reaction. Carbohydrate Research 2008, 343 (10-11) , 1790-1800. https://doi.org/10.1016/j.carres.2008.02.014
    16. Mayumi Takahashi, Shunsuke Daidouji, Motoo Shiro, Noriaki Minakawa, Akira Matsuda. Synthesis and crystal structure of 2′-deoxy-2′-fluoro-4′-thioribonucleosides: substrates for the synthesis of novel modified RNAs. Tetrahedron 2008, 64 (19) , 4313-4324. https://doi.org/10.1016/j.tet.2008.02.071
    17. Akimasa Matsugami, Takako Ohyama, Masashi Inada, Naonori Inoue, Noriaki Minakawa, Akira Matsuda, Masato Katahira. Unexpected A-form formation of 4′-thioDNA in solution, revealed by NMR, and the implications as to the mechanism of nuclease resistance. Nucleic Acids Research 2008, 36 (6) , 1805-1812. https://doi.org/10.1093/nar/gkn011
    18. Jun Toyohara, Maki Okada, Chie Toramatsu, Kazutoshi Suzuki, Toshiaki Irie. Feasibility studies of 4′-[methyl-11C]thiothymidine as a tumor proliferation imaging agent in mice. Nuclear Medicine and Biology 2008, 35 (1) , 67-74. https://doi.org/10.1016/j.nucmedbio.2007.10.001
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    20. Vı́ctor Ulgar, Óscar López, Inés Maya, José G Fernández-Bolaños, Mikael Bols. Synthesis of furan 4′-thio-C-nucleosides, their methylsulfonium and sulfoxide derivatives. Evaluation as glycosidase inhibitors. Tetrahedron 2003, 59 (16) , 2801-2809. https://doi.org/10.1016/S0040-4020(03)00339-9
    21. Yan Xu, Katsuhito Kino, Hiroshi Sugiyama. The Conformational Study of Two Carbocyclic Nucleosides: Why Carbocyclic Nucleic Acids (CarNAs) Form More Stable Duplexes with RNA than DNA Does. Journal of Biomolecular Structure and Dynamics 2002, 20 (3) , 437-446. https://doi.org/10.1080/07391102.2002.10506862
    22. Noriaki Minakawa, Daisuke Kaga, Yuka Kato, Kanji Endo, Motohiro Tanaka, Takuma Sasaki, Akira Matsuda. Synthesis and structural elucidation of 1-(3-C-ethynyl-4-thio-β- D -ribofuranosyl)cytosine (4′-thioECyd). J. Chem. Soc., Perkin Trans. 1 2002, 12 (19) , 2182-2189. https://doi.org/10.1039/B204993G
    23. Jose G. Fernändez-Bolaños, Najim A.L. Al-Masoudi, Inés Maya. Sugar derivatives having sulfur in the ring. 2001, 21-98. https://doi.org/10.1016/S0065-2318(01)57015-8
    24. G Inguaggiato, D Hughes, E De Clercq, J Balzarini, C Simons. Novel 6-Azapyrimidine-2′-Deoxy-4′-Thionucleosides: Synthesis, Biological Evaluation and Conformational Analysis. Antiviral Chemistry and Chemotherapy 1999, 10 (5) , 241-249. https://doi.org/10.1177/095632029901000503
    25. L. E. Bailey, M. L. García-Martin, H. Stender, G. Ball. Structural Studies of 5-Ethyl-2′-Deoxyuridine by Selective Pulse 1 H DPFGSE NOE Spectroscopy and PM3 Calculations. Nucleosides and Nucleotides 1999, 18 (4-5) , 1067-1068. https://doi.org/10.1080/15257779908041647
    26. Aleksej Yu. Denisov, E. V. Zamaratski, Tatiana V. Maltseva, Anders Sandström, Somer Bekiroglu, Karl-Heinz Altmann, Martin Egli, Jyoti Chattopadhyaya. The Solution Conformation of a Carbocyclic Analog of the Dickerson-Drew Dodecamer: Comparison with its own X-ray Structure and that of the NMR Structure of the Native Counterpart. Journal of Biomolecular Structure and Dynamics 1998, 16 (3) , 547-568. https://doi.org/10.1080/07391102.1998.10508269
    27. Alasdair C. MacCulloch, Richard T. Walker. A novel method for deuteration of 2′-deoxy-4′-thionucleosides. Tetrahedron 1998, 54 (41) , 12457-12464. https://doi.org/10.1016/S0040-4020(98)00727-3
    28. Jean Boivin, Laure Ramos, Samir Z. Zard. An expedient radical based approach to difluorophosphonate analogues of thionucleosides. Tetrahedron Letters 1998, 39 (38) , 6877-6880. https://doi.org/10.1016/S0040-4039(98)01501-9
    29. I. Basnak, Ming Sun, T. A. Hamor, N. Spencer, R. T. Walke. The Structure of 5-Cyclohexyl-2′-Deoxyuridine as Studied by X-Ray Crystallography and NMR Spectroscopy. Nucleosides and Nucleotides 1996, 15 (7-8) , 1275-1285. https://doi.org/10.1080/07328319608002429
    30. I. Basnak, M. Sun, P. L. Coe, R. T. Walker. The Synthesis of Some 5-Alkyl (Cycloalkyl)-Substituted 2′ -Deoxy-4′-Thiouridines. Nucleosides and Nucleotides 1996, 15 (1-3) , 121-134. https://doi.org/10.1080/07328319608002375
    31. David F. Ewing, Grahame Mackenzie. Configurational Assignment in 2′-Deoxy-4′-Thionucleosides - A Review. Nucleosides and Nucleotides 1996, 15 (1-3) , 809-820. https://doi.org/10.1080/07328319608002424
    32. T. J. Boggon, E. L. Hancox, K. E. McAuley-Hecht, B. A. Connolly, W. N. Hunter, T. Brown, R. T. Walker, G. A. Leonard. The Crystal Structure Analysis of d(CGCGAASSCGCG)2, a Synthetic DNA Dodecamer Duplex Containing Four 4'-Thio-2'-Deoxythymidine Nucleotides. Nucleic Acids Research 1996, 24 (5) , 951-961. https://doi.org/10.1093/nar/24.5.951
    33. William B. Parker, Sue C. Shaddix, Lucy M. Rose, Kamal N. Tiwari, John A. Montgomery, John A. Secrist, L.Lee Bennett. Metabolism and metabolic actions of 4′-thiothymidine in L1210 cells. Biochemical Pharmacology 1995, 50 (5) , 687-695. https://doi.org/10.1016/0006-2952(95)00178-3
    34. D. Galisteo, J.A.López Sastre, H.Martínez García, R.Nuñez Miguel. Conformational comparative analysis of 2′,3′-dideoxythymidine analogues by molecular mechanics calculations (chem-x) and by semiempirical methods (AM1). Journal of Molecular Structure 1995, 350 (2) , 147-160. https://doi.org/10.1016/0022-2860(94)08472-T
    35. Lak S. Jeong, Marc C. Nicklaus, Cliff George, Victor E. Marquez. Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with “up” hydroxyl groups. Tetrahedron Letters 1994, 35 (41) , 7569-7572. https://doi.org/10.1016/S0040-4039(00)78345-6
    36. I. Basnak, P. L. Coe, R. T. Walker. The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines. Nucleosides and Nucleotides 1994, 13 (1-3) , 163-175. https://doi.org/10.1080/15257779408013233
    37. I. Basnak, A. Balkan, P. L. Coe, R. T. Walker. The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines. Nucleosides and Nucleotides 1994, 13 (1-3) , 177-196. https://doi.org/10.1080/15257779408013234
    38. E.Louise Hancox, Thomas A. Hamor, Richard T. Walker. The chemical synthesis and x-ray structure of the sulfone of 4′-thiothymidine. Tetrahedron Letters 1994, 35 (8) , 1291-1294. https://doi.org/10.1016/0040-4039(94)88047-6
    39. Kamal N. Tiwari, John A. Montgomery, John A. Secrist. The Synthesis and Biological Activity of 1-(2-Deoxy-4-Thio-α;-L-Threo-Pentofuranosyl)Thymine. Nucleosides and Nucleotides 1993, 12 (8) , 841-846. https://doi.org/10.1080/07328319308018554
    40. Stanislaw F. Wnuk. Sulfur- and seleno-sugar modified nucleosides. Synthesis, chemical transformations and biological properties.. Tetrahedron 1993, 49 (44) , 9877-9936. https://doi.org/10.1016/S0040-4020(01)80190-3
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    Cite this: J. Am. Chem. Soc. 1992, 114, 25, 9936–9943
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja00051a028
    Published December 1, 1992
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