Alternative synthesis of cyclic IDP-carbocyclic ribose. Efficient cyclization of an 8-bromo-N1-[5-(phosphoryl)carbocyclic-ribosyl]inosine 5'- phenylthiophosphate derivative mediated by iodine

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5361-5364

  Fukuoka, Masayoshi ^a   Shuto, Satoshi ^a   Minakawa, Noriaki ^a   Ueno, Yoshihito ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Nucleic acid analogs; Nucleotides; Phosphorylation; Thiophosphoryl compounds

Indexed keywords

ADENOSINE DIPHOSPHATE RIBOSE; IODINE; NUCLEIC ACID; NUCLEOTIDE; PYRIDINE DERIVATIVE; RIBOSE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR DYNAMICS; OPTICAL ROTATION; PHOSPHORYLATION; POLYMERIZATION; REACTION ANALYSIS;

EID: 0033575502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00977-6     Document Type: Article

References (28)

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8. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
9. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
10. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
11. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
12. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
13. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
14. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
15. (a) Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta. 1993, 1178, 235-242. (b) Lee, H. C.; Aarhus, R.; Walseth, T. F. Science 1993, 261, 352-355. (c) Graeff, R. M; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267. (d) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706. (e) Zhang, F-J.; Gu, Q-M.; Jing, P.C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272. (f) Zhang, F-J.; Yamada, S.; Gu, Q-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208. (g) Zhang, F-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316. (h) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1356. (i) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230. (j) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60. (k) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1997, 695-696.
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19. 1-carbocyclic-ribosyladenosine derivatives was described: Hutchinson, E. J.; Taylor, B. F.; Blackburn, G. M. J. Chem. Soc. Chem. Commun. 1997, 1859-1860.
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21. The carbocyclic amine 11 was recovered in 87% yield after the reaction, and was repeatedly used.
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27. 3. The aqueous layer was filtered with a syringe filter (cellulose acetate), and then analyzed by HPLC [column, YMS-ODS-M-80, 4.6 × 150 mm; 5 - 80% MeCN/0.1 M TEAA buffer (pH 7.0), 30 min; 254 nm]. Compound 8 was eluted at 14.7 min which was identified with the authentic sample synthesized previously, and a peak observed at 3.1 min was unknown non-nucleosidic compound due to its UV spectrum.
28. 3 in HMPA/N-methylpyrrolidone (MPD): Shuto, S; Shirato, M; Sumita, Y; Ueno, Y; Matsuda, A. Tetrahedron Lett. 1998, 39, 7341-7344. (equation presented)