Efficient chemical synthesis of a pyrimidine (6-4) pyrimidone photoproduct analog and its properties

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2175-2179

  Satou, Kousuke ^a   Komatsu, Yasuo ^a   Torizawa, Takuya ^b   Kato, Koichi ^b   Shimada, Ichio ^b   Nikaido, Osamu ^c   Ohtsuka, Eiko ^d  

^a HOKKAIDO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

^d HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

Antibodies; Antigens; Nucleic acid analogs; Nucleic acids; Photochemistry

Indexed keywords

ANTIBODY; ANTIGEN; NUCLEIC ACID; PYRIMIDINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; KINETICS; MOLECULAR INTERACTION; PHOTOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0034719710     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00127-1     Document Type: Article

References (14)

1. Gentil, A.; Le Page, F.; Margot, A.; Lawrence, C. W.; Borden, A.; Sarasin, A. Nucleic Acids Res. 1996, 24, 1837-1840.
2. Kamiya, H.; Iwai, S.; Kasai, H. Nucleic Acids Res. 1998, 26, 2611-2617.
3. Todo, T.; Takemori, H.; Ryo, H.; Ihara, M.; Matsunaga, T.; Nikaido, O.; Sato, K.; Nomura, T. Nature 1993, 361, 371-374.
4. Iwai, S.; Shimizu, M.; Kamiya, H.; Ohtsuka, E. J. Am. Chem. Soc. 1996, 118, 7642-7643.
5. Butenandt, J.; Burgdorf, L. T.; Carell, T. Angew. Chem., Int. Ed. 1999, 38, 708-711.
6. Matteucci, M. Tetrahedron Lett. 1990, 31, 2385-2388.
7. Veeneman, G. H.; Van Der Marel, G. A.; Van Den Elst, H.; Van Boom, J. H. Tetrahedron 1991, 47, 1547-1562.
8. Compounds 4 and 6 were each dissolved in a 20% aqueous acetonitrile solution. The 1 mM solutions containing 4 or 6 were irradiated with UV-light (254 nm). After aliquots were taken from the solutions at each UV dose, the generation of the (6-4) photoproducts was analyzed by HPLC using a reverse phase column (μ-Bondasphere, C-18, 3.9 mm i.d.×150 mm, Waters), and the gradient was 10-100% B buffer content over 20 min (A buffer, 5% aqueous acetonitrile, 0.1 M triethylammonium acetate (TEAA); B buffer, 60% aqueous acetonitrile, 0.1 M TEAA). The elution was monitored by a photodiode array detector (Waters TM 996). Since both 5 and 7 absorb UV-light at 325 nm efficiently, the concentrations of those products were calculated from the peak areas at 325 nm.
9. 2). Compound 5 (82 mg, 0.13 mmol) was isolated by silica gel column chromatography (Wakogel, C-300).
10. + 611.2745, found 611.2741.
11. 4 and were purified on a reverse phase column (μ-Bondasphere, 3.9 mm i.d.×150 mm, Waters). The gradient for T[6c4]T-4 and T[6c4]T-8, which were covalently connected with biotins, were 0-100% and 20-40% B buffer content, respectively, over 20 min (A buffer, 5% aqueous acetonitrile, 0.1 M TEAA; B buffer, 25% aqueous acetonitrile, 0.1 M TEAA). The overall yields of T[6c4]T-4 and T[6c4]T-8 were 31% and 14%, respectively.
12. Mori, T.; Nakane, M.; Hattori, T.; Matsunaga, T.; Ihara, M.; Nikaido, O. Photochem. Photobiol. 1991, 54, 225-232.
13. Kobayashi, H.; Morioka, H.; Torizawa, T.; Kato, K.; Shimada, I.; Nikaido, O.; Ohtsuka, E. J. Biochem. 1998, 123, 182-188.
14. Torizawa, T.; Kato, K.; Kato, J.; Kobayashi, H.; Komatsu, Y.; Morioka, H.; Nikaido, O.; Ohtsuka, E.; Shimada, I. J. Mol. Biol. 1999, 290, 731-740.