SCOPUS 정보 검색 플랫폼

Volumn 74, Issue 2, 2001, Pages 381-398

NMR conformational study reveals that S-C-N anomeric effect in thionucleosides is weaker than O-C-N anomeric effect in natural nucleosides

(2) Črnugelj, Martin a Plavec, Janez a

a NATIONAL INSTITUTE OF CHEMISTRY (Slovenia)

Author keywords

Anomeric effect; Conformational analysis; NMR; Nucleoside; Pseudorotational equilibrium

Indexed keywords

EID: 0042908606 PISSN: 00111643 EISSN: None Source Type: Journal
DOI: None Document Type: Article

Times cited : (3)

References (43)

1
- 0003458038
- Springer Verlag, New York
- W. Saenger, Principles of Nucleic Acid Structure, Springer Verlag, New York, 1984.
- (1984) Principles of Nucleic Acid Structure
- Saenger, W.¹

2
- 0015511563
- C. Altona and M. Sundaralingam, J. Am. Chem. Soc. 94 (1972) 8205-8212.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 8205-8212
- Altona, C.¹ Sundaralingam, M.²

3
- 0015913888
- C. Altona and M. Sundaralingam, J. Am. Chem. Soc. 95 (1973) 2333-2344.
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 2333-2344
- Altona, C.¹ Sundaralingam, M.²

4
- 0001120142
- J. Plavec, W. Tong, and J. Chattopadhyaya, J. Am. Chem. Soc. 115 (1993) 9734-9746.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 9734-9746
- Plavec, J.¹ Tong, W.² Chattopadhyaya, J.³

5
- 0003417547
- Uppsala University Press, Uppsala, Sweden
- C. Thibaudeau and J. Chattopadhyaya, Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications, Uppsala University Press, Uppsala, Sweden, 1999.
- (1999) Stereoelectronic Effects in Nucleosides and Nucleotides and Their Structural Implications
- Thibaudeau, C.¹ Chattopadhyaya, J.²

6
- 37049070658
- J. Plavec, N. Garg, and J. Chattopadhyaya, J. Chem. Soc., Chem. Commun. (1993) 1011-1014.
- (1993) J. Chem. Soc., Chem. Commun. , pp. 1011-1014
- Plavec, J.¹ Garg, N.² Chattopadhyaya, J.³

7
- 0026473019
- J. Plavec, L. H. Koole, and J. Chattopadhyaya, J. Biochem. Biophys. Meth. 25 (1992) 253-272.
- (1992) J. Biochem. Biophys. Meth. , vol.25 , pp. 253-272
- Plavec, J.¹ Koole, L.H.² Chattopadhyaya, J.³

8
- 0027077877
- L. H. Koole, J. Plavec, H. Liu, B. R. Vincent, M. R. Dyson, P. L. Coe, R. T. Walker, G. W. Hardy, G. S. Rahim, and J. Chattopadhyaya, J. Am. Chem. Soc. 114 (1992) 9936-9943.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 9936-9943
- Koole, L.H.¹ Plavec, J.² Liu, H.³ Vincent, B.R.⁴ Dyson, M.R.⁵ Coe, P.L.⁶ Walker, R.T.⁷ Hardy, G.W.⁸ Rahim, G.S.⁹ Chattopadhyaya, J.¹⁰

9
- 37049082958
- J. Plavec, C. Thibaudeau, G. Viswanadham, C. Sund, and J. Chattopadhyaya, J. Chem. Soc., Chem. Commun. (1994) 781-783.
- (1994) J. Chem. Soc., Chem. Commun. , pp. 781-783
- Plavec, J.¹ Thibaudeau, C.² Viswanadham, G.³ Sund, C.⁴ Chattopadhyaya, J.⁵

10
- 37049068858
- C. Thibaudeau, J. Plavec, K. A. Watanabe, and J. Chattopadhyaya, J. Chem. Soc., Chem. Commun. (1994) 537-540.
- (1994) J. Chem. Soc., Chem. Commun. , pp. 537-540
- Thibaudeau, C.¹ Plavec, J.² Watanabe, K.A.³ Chattopadhyaya, J.⁴

11
- 0001536337
- C. Thibaudeau, J. Plavec, N. Garg, A. Papchikhin, and J. Chattopadhyaya, J. Am. Chem. Soc. 116 (1994) 4038-4043.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 4038-4043
- Thibaudeau, C.¹ Plavec, J.² Garg, N.³ Papchikhin, A.⁴ Chattopadhyaya, J.⁵

12
- 0028106961
- J. Plavec, C. Thibaudeau, and J. Chattopadhyaya, J. Am. Chem. Soc. 116 (1994) 6558-6560.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 6558-6560
- Plavec, J.¹ Thibaudeau, C.² Chattopadhyaya, J.³

13
- 0027942479
- C. Thibaudeau, J. Plavec, and J. Chattopadhyaya, J. Am. Chem. Soc. 116 (1994) 8033-8037.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8033-8037
- Thibaudeau, C.¹ Plavec, J.² Chattopadhyaya, J.³

14
- 0028789675
- J. Plavec, C. Thibaudeau, G. Viswanadham, A. Sandström, and J. Chattopadhyaya, Tetrahedron 51 (1995) 11775-11792.
- (1995) Tetrahedron , vol.51 , pp. 11775-11792
- Plavec, J.¹ Thibaudeau, C.² Viswanadham, G.³ Sandström, A.⁴ Chattopadhyaya, J.⁵

15
- 0042798375
- Ph.D. Thesis, Department of Bioorganic Chemistry, Uppsala University, Uppsala University Press, Uppsala, Sweden
- J. Plavec, Ph.D. Thesis, Department of Bioorganic Chemistry, Uppsala University, Uppsala University Press, Uppsala, Sweden, 1995.
- (1995)
- Plavec, J.¹

16
- 0001114974
- C. Thibaudeau, J. Plavec, and J. Chattopadhyaya, J. Org. Chem. 61 (1996) 266-286.
- (1996) J. Org. Chem. , vol.61 , pp. 266-286
- Thibaudeau, C.¹ Plavec, J.² Chattopadhyaya, J.³

17
- 0000408963
- J. Plavec, C. Thibaudeau, and J. Chattopadhyaya, Pure & Appl. Chem. 68 (1996) 2137-2145.
- (1996) Pure & Appl. Chem. , vol.68 , pp. 2137-2145
- Plavec, J.¹ Thibaudeau, C.² Chattopadhyaya, J.³

18
- 0030944463
- I. Luyten, C. Thibaudeau, A. Sandström, and J. Chattopadhyaya, Tetrahedron 53 (1997) 6433-6464.
- (1997) Tetrahedron , vol.53 , pp. 6433-6464
- Luyten, I.¹ Thibaudeau, C.² Sandström, A.³ Chattopadhyaya, J.⁴

19
- 0032567873
- C. Thibaudeau, A. Foldesi, and J. Chattopadhyaya, Tetrahedron 54 (1998) 1867-1900.
- (1998) Tetrahedron , vol.54 , pp. 1867-1900
- Thibaudeau, C.¹ Foldesi, A.² Chattopadhyaya, J.³

20
- 0006484295
- I. Luyten, C. Thibaudeau, and J. Chattopadhyaya, J. Org. Chem. 62 (1997) 8800-8808.
- (1997) J. Org. Chem. , vol.62 , pp. 8800-8808
- Luyten, I.¹ Thibaudeau, C.² Chattopadhyaya, J.³

21
- 0031760869
- C. Thibaudeau and J. Chattopadhyaya, Nucleosides & Nucleotides 17 (1998) 1589-1603.
- (1998) Nucleosides & Nucleotides , vol.17 , pp. 1589-1603
- Thibaudeau, C.¹ Chattopadhyaya, J.²

22
- 0031729358
- I. Luyten, J. Matulic-Adamic, L. Beigelman, and J. Chattopadhyaya, Nucleosides & Nucleotides 17 (1998) 1605-1611.
- (1998) Nucleosides & Nucleotides , vol.17 , pp. 1605-1611
- Luyten, I.¹ Matulic-Adamic, J.² Beigelman, L.³ Chattopadhyaya, J.⁴

23
- 0030857229
- C. Thibaudeau and J. Chattopadhyaya, Nucleosides & Nucleotides 16 (1997) 523-529.
- (1997) Nucleosides & Nucleotides , vol.16 , pp. 523-529
- Thibaudeau, C.¹ Chattopadhyaya, J.²

24
- 0031902333
- C. Thibaudeau, A. Kumar, S. Bekiroglu, A. Matsuda, V. E. Marquez, and J. Chattopadhyaya, J. Org. Chem. 63 (1998) 5447-5462.
- (1998) J. Org. Chem. , vol.63 , pp. 5447-5462
- Thibaudeau, C.¹ Kumar, A.² Bekiroglu, S.³ Matsuda, A.⁴ Marquez, V.E.⁵ Chattopadhyaya, J.⁶

25
- 0032565093
- M. Polak, B. Mohar, J. Kobe, and J. Plavec, J. Am. Chem. Soc. 120 (1998) 2508-2513.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2508-2513
- Polak, M.¹ Mohar, B.² Kobe, J.³ Plavec, J.⁴

26
- 0026736199
- E. Juaristi and G. Cuevas, Tetrahedron 48 (1992) 5019-5087.
- (1992) Tetrahedron , vol.48 , pp. 5019-5087
- Juaristi, E.¹ Cuevas, G.²

27
- 0024930829
- Academic Press, San Diego
- I. Tvaroska and T. Bleha (Eds.), Anomeric and Exo-Anomeric Effects in Carbohydrate Chemistry, Academic Press, San Diego, 1989, Vol. 47.
- (1989) Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry , vol.47
- Tvaroska, I.¹ Bleha, T.²

28
- 0010769937
- G. R. J. Thatcher, (Ed.), American Chemical Society, Washington, DC
- A. J. Kirby and N. H. Williams, in: G. R. J. Thatcher, (Ed.), The Anomeric Effect and Associated Stereoelectronic Effects, 539 Ed., American Chemical Society, Washington, DC, 1993, pp. 55-69.
- (1993) The Anomeric Effect and Associated Stereoelectronic Effects, 539 Ed. , pp. 55-69
- Kirby, A.J.¹ Williams, N.H.²

29
- 0003258093
- P. P. Graczyk and M. Mikolajczyk, Top. Stereochem. 21 (1994) 159-349.
- (1994) Top. Stereochem. , vol.21 , pp. 159-349
- Graczyk, P.P.¹ Mikolajczyk, M.²

30
- 0034143043
- M. Črnugelj, D. Dukhan, J. L. Barascut, J. L. Imbach, and J. Plavec, J. Chem. Soc., Perkin Trans. 2 (2000) 255-262.
- (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 255-262
- Črnugelj, M.¹ Dukhan, D.² Barascut, J.L.³ Imbach, J.L.⁴ Plavec, J.⁵

31
- 0033447201
- H. Yuasa and H. Hashimoto, Rev. Heteroatom Chem. 19 (1999) 35-65.
- (1999) Rev. Heteroatom Chem. , vol.19 , pp. 35-65
- Yuasa, H.¹ Hashimoto, H.²

32
- 0001435913
- M. A. Clement and S. H. Berger, Med. Chem. Res. 2 (1992) 154-164.
- (1992) Med. Chem. Res. , vol.2 , pp. 154-164
- Clement, M.A.¹ Berger, S.H.²

33
- 0042798373
- Y. S. Sanghvi and P. D. Cook, (Eds.), American Chemical Society, Washington, DC
- L. Bellon, C. Leydier, J.-L. Barascut, G. Maury, and J.-L. Imbach, in: Y. S. Sanghvi and P. D. Cook, (Eds.), Carbohydrate Modifications in Antisense Research, 580 Ed., American Chemical Society, Washington, DC, 1994, pp. 68-79.
- (1994) Carbohydrate Modifications in Antisense Research, 580 Ed. , pp. 68-79
- Bellon, L.¹ Leydier, C.² Barascut, J.-L.³ Maury, G.⁴ Imbach, J.-L.⁵

34
- 0041796083
- Varian Inc., Palo Alto
- VNMR program, revision 6.1A, Varian Inc., Palo Alto, 1999.
- (1999) VNMR Program, Revision 6.1A

35
- 0038801579
- Leiden University, Leiden, Netherlands
- C. Haasnoot, F. A. A. M. de Leeuw, D. Huckriede, J. van Wijk, and C. Altona, PSEUROT version 6.0, Leiden University, Leiden, Netherlands, 1993.
- (1993) PSEUROT Version 6.0
- Haasnoot, C.¹ De Leeuw, F.A.A.M.² Huckriede, D.³ Van Wijk, J.⁴ Altona, C.⁵

36
- 20444483055
- C. A. G. Haasnoot, F. A. A. M. de Leeuw, and C. Altona, Tetrahedron 36 (1980) 2783-2792.
- (1980) Tetrahedron , vol.36 , pp. 2783-2792
- Haasnoot, C.A.G.¹ De Leeuw, F.A.A.M.² Altona, C.³

37
- 84989036214
- C. Altona, R. Francke, R. de Haan, J. H. Ippel, G. J. Daalmans, A. J. A. Westra Hoekzema, and J. van Wijk, Magn. Reson. Chem. 32 (1994) 670-678.
- (1994) Magn. Reson. Chem. , vol.32 , pp. 670-678
- Altona, C.¹ Francke, R.² De Haan, R.³ Ippel, J.H.⁴ Daalmans, G.J.⁵ Westra Hoekzema, A.J.A.⁶ Van Wijk, J.⁷

38
- 0041295609
- note
- 4 ≡ [C3′-C4′-S4′-C1′].

39
- 0010789368
- E. Diez, A. L. Esteban, F. J. Bermejo, C. Altona, and F. A. A. M. de Leeuw, J. Mol. Struct. 125 (1984) 49-65.
- (1984) J. Mol. Struct. , vol.125 , pp. 49-65
- Diez, E.¹ Esteban, A.L.² Bermejo, F.J.³ Altona, C.⁴ De Leeuw, F.A.A.M.⁵

40
- 0004133516
- Gaussian Inc., Pittsburgh, PA
- M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheesman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, P. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian 94, Rev. D.1, Gaussian Inc., Pittsburgh, PA, 1995.
- (1995) Gaussian 94, Rev. D.1
- Frisch, M.J.¹ Trucks, G.W.² Schlegel, H.B.³ Gill, P.M.W.⁴ Johnson, B.G.⁵ Robb, M.A.⁶ Cheesman, J.R.⁷ Keith, T.⁸ Petersson, G.A.⁹ Montgomery, J.A.¹⁰ Raghavachari, K.¹¹ Al-Laham, M.A.¹² Zakrzewski, V.G.¹³ Ortiz, J.V.¹⁴ Foresman, J.B.¹⁵ Cioslowski, J.¹⁶ Stefanov, P.B.¹⁷ Nanayakkara, A.¹⁸ Challacombe, M.¹⁹ Peng, C.Y.²⁰ more..

41
- 0004133516
- Gaussian Inc., Pittsburgh, PA
- M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheesman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratman, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, K. M. Q. Cui, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Rev. A.5, Gaussian Inc., Pittsburgh, PA, 1998.
- (1998) Gaussian 98, Rev. A.5
- Frisch, M.J.¹ Trucks, G.W.² Schlegel, H.B.³ Scuseria, G.E.⁴ Robb, M.A.⁵ Cheesman, J.R.⁶ Zakrzewski, V.G.⁷ Montgomery, J.A.⁸ Stratman, R.E.⁹ Burant, J.C.¹⁰ Dapprich, S.¹¹ Millam, J.M.¹² Daniels, A.D.¹³ Kudin, K.N.¹⁴ Strain, M.C.¹⁵ Farkas, O.¹⁶ Tomasi, J.¹⁷ Barone, V.¹⁸ Cossi, M.¹⁹ Cammi, R.²⁰ more..

42
- 84986492501
- F. A. A. M. de Leeuw and C. Altona, J. Comp. Chem. 4 (1983) 428-437.
- (1983) J. Comp. Chem. , vol.4 , pp. 428-437
- De Leeuw, F.A.A.M.¹ Altona, C.²

43
- 84985069908
- H. P. M. de Leeuw, C. A. G. Haasnoot, and C. Altona, Isr. J. Chem. 20 (1980) 108-126.
- (1980) Isr. J. Chem. , vol.20 , pp. 108-126
- De Leeuw, H.P.M.¹ Haasnoot, C.A.G.² Altona, C.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.