344
D. Prukała
Vol. 43
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Schultz, R. A. Lerner, K. D. Janda, Science, 290, 307 (2000).
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2481 (1983).
General Procedure for the Preparation of (E)-4-Chlorocarbonyl-
alkoxystilbenes 1-8.
A mixture of 0.015 mole of appropriate (E)-4-stilbenyl-
oxyalkylcarboxylic acids and thionyl chloride (6 mL, 0.075
mole) in dry benzene (20 mL) was heated under reflux for 1 hr.
Then the thionyl chloride and the solvent were evaporated in
vacuo. The solid isolated was suspended in dry benzene and fil-
tered trough silica gel (Merck 60 0.063-0.100mm). The solvent
was removed again. Compounds 1-8 were shown to be analyti-
cally pure and were used without any further purification.
4
General Procedure for the Preparation of N -(E)-stilbeny-
[7] N. K. Kochetkov, V. N. Shibaev and A. A. Kost,
Tetrahedron Letters, 1993 (1971)
loxyalkylcarbonyl-cytosines 9-16.
Cytosine (1.11 g, 0.01 mole) and DMAP (N,N-dimethyl-
aminopyridine 0.040 g 0.0003 mole) was suspended in dry pyri-
dine (20 mL) and boiled under reflux. Then the boiling mixture
was treated dropwise with the solution of 0.015 mole of appropri-
ate (E)-4-chlorocarbonylalkoxystilbene 1-8 in dry benzene (2
mL). The reaction mixture was then allowed to reflux for 6 hrs.
The solvent was then removed in vacuo and the solid was treated
with dry methanol and boiled. The precipitated solid was col-
lected by filtration from hot solvent. This procedure was repeated
three times. Solids 9-16 were collected and dried under vacuum
at room temperature. The physicochemical properties of 9-16 are
given in Table I.
[8] R. S. Hosmane and N. J. Leonard, J. Org. Chem., 46, 1457
(1981).
[9] N. J. Leonard and G. L. Tolman, Ann. N. Y. Acad. Sci.,
255, 43 (1975).
[10]
L. Brand and J. R. Gohlke, Annual Review of
Biochemistry, 41, 843 (1972).
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11, 454 (1998).
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Chem., 66, 763 (1992).
[13] K. Wüthrich , NMR of Proteins and Nucleic Acids, John
Wiley&Sons, New York, N.Y. 1986.
[14] J. N. S. Evans, Biomolecular NMR Spectroscopy; Oxford
University Press, New York, 1995.
4
General Procedure for the Preparation of N -(E)-Stilbenyloxy-
[15] C. E. Aun, T. Y. Clarkson and D. A. R. Happer, J. Chem.
Soc., Perkin Trans II, 645 (1990).
[16] E. Wyrzykiewicz J. Grzesiak and W. Prukała, Magn.
Reson. Chem., 26, 529 (1988).
[17] T. H. Fischer and P. T. Shultz, Magn. Reson. Chem., 29,
966 (1991).
[18] K. H. Galm, S. L. Eng, T. I. -Ho, and Y. -Ch. Liu, J. Chin.
Chem. Soc., 38, 591 (1991).
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Reson., 22, 237 (1984).
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[21] E. A. Braude, J. Chem. Soc., 1902 (1949).
[22] D. F. Detar and L. A. Carpino, J. Am. Chem. Soc., 78, 475
(1945).
[23] H. W. Thompson and P. Torkington, J. Chem. Soc., 640
(1945).
alkylcarbonyl-1-methyl Cytosines 17-24.
1-Methylcytosine (1.25 g 0.01 mole) and DMAP (N,N-
dimethylaminopyridine 0.040 g, 0.0003 mole) was suspended in
dry pyridine (20 mL) and boiled under reflux. Then the boiling
mixture was treated dropwise with the solution of 0.015 mole of
appropriate (E)-4-chlorocarbonylalkoxystilbene 1-8 in dry ben-
zene (2 mL). The reaction mixture was then reflux for 5 hrs. Then
the solvent was removed under vacuum, and the solid precipi-
tated was treated with dry methanol and boiled. The solid of 17,
19, and 21 was collected by filtration from hot solvent and puri-
fied like described above. The compounds 18, 20, 22, 23, 24 were
separated by column chromatography (silica gel Merck 60 0,063-
0,100mm, CHCl :CH OH 30:1). The physicochemical properties
3
3
of 17-24 are given in Table I.
[24] M. Oki and H. Kunimoto, Spectrochimica Acta, 19, 1463
(1963)
REFERENCES AND NOTES
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