4434
Y. Ueno et al. / Bioorg. Med. Chem. Lett. 14 (2004) 4431–4434
J=5.2Hz, 30-OH), 4.37 (2H, m, 10-H), 4.21 (1H, m, 20-H),
Acknowledgements
3.75–3.69 (7H, m, 30-H and OMe·2), 3.10 (1H, dd,
J=11.3 and 5.0Hz, 40-H), 3.03 (1H, dd, J=11.3 and
6.4Hz, 40-H), 0.57 (9H, s, Sit-Bu), ꢀ0.30 (3H, s, SiMe),
ꢀ0.54 (3H, s, SiMe), the assignments were in agreement
with COSY spectrum; FAB-HRMS calcd for
C43H50N5O6Si (MH+), 760.3530; found, 760.3535.
This research was in part supported by a Grant-in-Aid
for Scientific Research (B) (KAKENHI 15390036) from
Japan Society for the Promotion of Science (JSPS).
13. Physical data of 9: 1H NMR (400MHz, DMSO-d6): d
11.12 (1H, s, 6-NH), 8.70 (1H, s, 8- or 2-H), 8.31 (1H, s, 2-
or 8-H), 8.05–6.86 (18H, m, Bz and DMTr), 5.21 (1H, d,
J=5.2Hz, 20-OH), 4.48 (1H, d, J=10.0Hz, 10-H), 4.09–
4.05 (2H, m, 10-H and 20-H), 3.82 (1H, m, 30-H), 3.72 (6H,
s, OMe·2), 3.19 (1H, dd, J=9.9 and 5.2Hz, 40-H), 3.05
(1H, dd, J=9.9 and 5.4Hz, 40-H), 0.85 (9H, s, Sit-Bu), 0.08
(3H, s, SiMe), ꢀ0.06 (3H, s, SiMe), the assignments were
in agreement with COSY spectrum; FAB-HRMS calcd for
C43H50N5O6Si (MH+), 760.3530; found, 760.3535.
References and notes
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8. Chu, C. K.; Cutler, S. J. J. Heterocycl. Chem. 1986, 23,
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9. Synthesis of the 2–5A analogs consisting of 9-[(20R,40S)-
10,50-dihydroxy-40-hydroxymethyl-30-oxapent-2-yl]adenine
has been reported: Mikhailov, S. N.; Pfleiderer, W.
Tetrahedron Lett. 1985, 26, 2059.
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34, 4835.
14. Physical data of 10: 31P NMR (162MHz, CDCl3): d
149.78, 146.81; FAB-HRMS calcd for C52H67Z7O7PSi
(MH+), 960.4609; found, 960.4612.
15. The phophoramidite 11 was synthesized as reported
previously.16 The phophoramidite 1217 was purchased
from GLEN Research.
16. Ueno, Y.; Kato, Y.; Okatani, S.; Ishida, N.; Nakanishi,
M.; Kitade, Y. Bioconjugate Chem. 2003, 14, 690.
17. Horn, T.; Urdea, M. S. Tetrahedron. Lett. 1986, 27, 4705.
18. Data of MALDI-TOF/MS. 2–5A 14: calcd for
C39H51N20O24P4 (MH+), 1307.2; found, 1307.1. 2–5A
15: calcd for C39H51N20O24P4 (MH+), 1307.2; found,
1306.0. The oligodeoxynucleotide 16: calcd for C169H205
N85O89P16 (M+), 5346.5; found, 5346.2.
-
11. Hirota, K.; Monguchi, Y.; Sajiki, H.; Sako, M.; Kitade, Y.
J. Chem. Soc., Perkin. Trans. 1 1998, 941.
12. Physical data of 8: 1H NMR (400MHz, DMSO-d6): d
11.13 (1H, s, 6-NH), 8.70 (1H, s, 8- or 2-H), 8.33 (1H, s, 2-
or 8-H), 8.06–6.86 (18H, m, Bz and DMTr), 5.44 (1H, d,
19. Yoshimura, A.; Nakanishi, M.; Yatome, C.; Kitade, Y. J.
Biochem. 2002, 132, 643.
20. The extinction coefficients of the 2–5As at 260nm were
estimated as 4.16·104.