Abstract
The method of modification of heterocyclic bases of nucleic acids with chloroacetaldehyde and other α-halo carbonyl compounds is examined in this review. The mechanism, kinetics, and scope of the reaction, the chemical properties of modified derivatives of adenine and cytosine, and the possibilities of the application of etheno derivatives of adenine and cytosine in biochemistry and molecular biology are discussed.
Similar content being viewed by others
Literature cited
N. K. Kochetkov, V. N. Shibaev, and A. A. Kost, Tetrahedron Lett., No. 22, 1993 (1971).
N. K. Kochetkov, V. N. Shibaev, and A. A. Kost, Dokl. Akad. Nauk SSSR,205, 100 (1972).
N. K. Kochetkov, V. N. Shibaev, and A. A. Kost, Dokl. Akad. Nauk SSSR,213, 1327 (1973).
N. J. Leonard and G. L. Tolman, Ann. New York Acad. Sci.,255, 43 (1975).
R. W. Thomas and N. J. Leonard, Heterocycles,5, 839 (1976).
J. R. Barrio, J. A. Secrist III, and N. J. Leonard, Biochem. Biophys. Res. Commun.,46, 597 (1972).
J. A. Secrist III, J. R. Barrio, N. J. Leonard, and G. Weber, Biochemistry,11, 3499 (1972).
J. A. Secrist III, J. R. Barrio, and N. J. Leonard, Fed. Proc.,31, 494 (1972).
J. A. Secrist III, J. R. Barrio, N. J. Leonard, C. Villar-Palasi, and A. G. Gilman, Science,177, 279 (1972).
R. D. Spencer, G. Weber, G. L. Tolman, J. R. Barrio, and N. J. Leonard, Eur. J. Biochem.,42, 425 (1974).
A. P. Razzhivin (Razjivin), A. A. Kost, and V. N. Shibaev, Stud. Biophys.,51, 29 (1975).
V. N. Shibaev, A. A. Kost, N. K. Kochetkov, A. P. Razzhivin (Razjivin), and S. V. Ermolin, Stud. Biophys.,69, 91 (1978).
S. V. Ermolin, A. A. Kost, M. V. Ivanov, and N. K. Nagradova, Dokl. Akad. Nauk SSSR,238. 245 (1978).
G. E. Dobretsov, Advances in Science. Molecular Biology [in Russian], Vol. 6, VINITI, Moscow (1975), p. 34.
J. A. Secrist III, J. R. Barrio, and N. J. Leonard, Science,175, 646 (1972).
N. J. Leonard, G. L. Tolman, and J. R. Barrio, Biochemistry,13, 4869 (1974).
R. K. Ledneva, A. P. Razzhivin (Razjivin), A. A. Kost, and A. A. Bogdanov, Nucleic Acids Res.,5, 4225 (1978).
R. F. Steiner, W. Kinnier, A. Lunasin, and J. Delac, Biochem. Biophys. Acta,294, 24 (1973).
S. D. Rose, Biochem. Biophys. Acta,361, 231 (1974).
D. A. Hilborn and G. G. Hammes, Biochemistry,12, 983 (1973).
L. V. Vorob'ev, A. I. Kotel'nikov, A. A. Kost, and R. I. Gvozdev, Bioorg. Khim.,1, 208 (1975).
J. R. Barrio, J. A. Secrist III, and N. J. Leonard, Proc. Nat. Acad. Sci. United States,69, 2039 (1972).
R. A. Harvey and S. Damble, FEBS Lett.,26, 341 (1972).
A. Måhlen, Eur. J. Biochem.,36, 342 (1973).
M. Moskophidis and W. Friedrich, Z. Naturforsch.,30, 460 (1975).
R. N. Prasad and D. L. Garmaise, US Patent No. 3830796 (1974); Chem. Abstr.,81, 63941a (1974).
G. H. Jones and J. G. Moffatt, US Patent No. 3872098 (1975); Chem. Abstr.,84, 150916b (1976).
R. N. Prasad and D. L. Gamaise, US Patent No. 3931401 (1976); Chem. Abstr.,85, 177891a (1976).
T. Kawanabe and M. Machida, West German Patent No. 2365720 (1976); Chem. Abstr.,84, 150920y (1976).
S. M. Zhenodarova, É. A. Sedel'nikova, O. A. Smolyaninova, V. N. Shibaev, and A. A. Kost, Bioorg. Khim.,1, 1345 (1975).
G. H. Jones, D. V. K. Murthy, D. Tegg, R. Golling, and J. G. Moffatt, Biochem. Biophys. Res. Commun.,53, 1338 (1973).
J. A. Secrist III, J. R. Barrio, N. J. Leonard, and L. G. Dammann, US Patent No. 3893998 (1975); Chem. Abstr.,85, 177890w (1976).
J. R. Barrio, L. G. Dammann, L. H. Kirkegaard, R. L. Switzer, and N. J. Leonard, J. Am. Chem. Soc.,95, 961 (1973).
J. C. Greenfield, N. J. Leonard, and R. I. Gumport, Biochemistry,14, 698 (1975).
J. R. Barrio, P. D. Sattsangi, B. A. Gruber, L. G. Dammann, and N. J. Leonard, J. Am. Chem. Soc.,98, 7408 (1976).
K. Senga, R. K. Robins, and D. E. O'Brien, J. Heterocycl. Chem.,12, 1043 (1975).
D. W. Jacobson, P. M. Digirolamo, and F. M. Huennekens, Mol. Pharmacol.,11, 174 (1975).
N. Yamaji and M. Kato, Chem. Lett., No. 4, 311 (1975).
J. D. Scarm and L. B. Townsend, Tetrahedron Lett., No. 14, 1345 (1974).
G. H. Jones and J. G. Moffatt, West German Patent No. 2350608 (1974); Chem. Abstr.,81, 13760v (1974).
W. L. Mosby, Heterocyclic Systems with Bridgehead Nitrogen Atoms, Vol. 2, Interscience, New York-London (1961), p. 540.
J. Biernat, J. Ciesiolka, P. Gornicki, R. W. Adamiak, W. J. Krzyzosiak, and M. Wiewiorowski, Nucleic Acids Res.,5, 789 (1978).
R. Shapiro, B. J. Cohen, S.-J. Shiney, and H. Maurer, Biochemistry,8, 238 (1969).
H. Kasai, M. Goto, K. Ikeda, M. Zama, Y. Mizuno, S. Takemura, S. Matsuura, T. Sugimoto, and T. Goto, Biochemistry,15, 898 (1976).
P. D. Sattsangi, N. J. Leonard, and C. R. Frihart, J. Org. Chem.,42, 3292 (1977).
N. K. Kochetkov, É. I. Budovskii, E. D. Sverdlov, N. A. Simukova, M. F. Turchinskii, and V. N. Shibaev, The Organic Chemistry of Nucleic Acids [in Russian], Khimiya, Moscow (1970), p. 414.
A. E. Chichibabin, Zh. Russ. Fiz.-Khim. Ova.,57, 421 (1925).
A. H.-J. Wang, L. G. Dammann, J. R. Barrio, and I. C. Paul, J. Am. Chem. Soc.,96, 1205 (1974).
N. K. Kochetkov, A. N. Kost, V. N. Shibaev, R. S. Sagitullin, A. A. Kost, and Yu. V. Zav'yalov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2766 (1975).
R. B. Meyr, D. A. Shuman, R. K. Robins, J. R. Miller, and L. N. Simon, J. Med. Chem.,16, 1319 (1973).
N. K. Kochetkov, V. N. Shibaev, A. A. Kost, A. P. Razzhivin, and S. V. Ermolin, Dokl. Akad. Nauk SSSR,234, 227 (1977).
A. A. Kost, and S. V. Ermolin, Nucleic Acids Res. Special Publ., No. 4, 197 (1978).
N. K. Kochetkov, V. N. Shibaev, A. A. Kost, A. P. Razzhivin (Razjivin), and A. Yu. Borisov, Nucleic Acids Res.,3, 1341 (1976).
M. Perk, H. Isemura, H. Yuki, and K. Takiura, Yakugaku Zasshi,95, 68 (1975).
E. Abignete, P. DeCaprariis, and F. Arena, Ann. Chim. (Rome),63, 619 (1973).
N. O. Saldabol, L. L. Zeligman, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 1, 137 (1973).
I. P. Rudakova, A. M. Yurkevich, and V. A. Yakovlev, Dokl. Akad. Nauk SSSR,218, 588 (1974).
E. Zbiral and E. Hugl, Tetrahedron Lett., No. 5, 439 (1972).
G. B. Chheda, S. P. Dutta, A. Mittelman, and L. Baczynskyj, Tetrahedron Lett., No. 5, 433 (1974).
N. K. Kochetkov, V. N. Shibaev, A. A. Kost, A. P. Razzhivin (Razjivin), and S. V. Ermolin, Dokl. Akad. Nauk SSSR,234, 1339 (1977).
K. Kimura, M. Nakanishi, T. Yamamoto, and M. Tsuboi, J. Biochem.,81, 1699 (1977).
P. Guerret, R. Jacquier, and G. Maury, J. Heterocycl. Chem.,8, 643 (1971).
B. S. Thyagarajan (ed.), Mechanisms of Molecular Migrations, Vol. 1, Interscience, New York-London-Sydney-Toronto (1968), p. 45.
B. G. Yasnitskii and Ts. I. Satanovskaya, Zh. Obshch. Khim.,34, 1034 (1964).
J. Biernet, J. Ciesolka, P. Gornicki, W. J. Krzyzosiak, and M. Wiewiorowski, Nucleic Acids Res. Special Publ., No. 4, 203 (1978).
E. M. Evleth and D. A. Lerner, Photochem. Photobiol.,26, 103 (1977).
A. A. Kost, Master's Dissertation, Moscow (1975).
K. F. Yip and K. C. Tsou, Tetrahedron Lett., No. 33, 3087 (1973).
K. C. Tsou, K. F. Yip, and K. W. Lo, Anal. Biochem.,60, 163 (1974).
K. F. Yip and K. C. Tsou, J. Org. Chem.,40, 1066 (1975).
R. Wetzel and F. Eckstein, J. Org. Chem.,40, 658 (1975).
N. Yamaji, Y. Yuasa, and M. Kato, Chem. Pharm. Bull. (Tokyo),24, 1561 (1976).
R. M. K. Dale, E. Martin, D. C. Livingston, and D. C. Ward, Biochemistry,14, 2447 (1975).
M. V. Ivanov and A. A. Kost, Usp. Biol. Khim.,21, 28 (1980).
W. Hoehne and P. Heitmann, Anal. Biochem.,69, 607 (1975).
C.-Yu Lee and J. Everse, Arch. Biochem. Biophys.,157, 83 (1973).
R. I. Gvozdev, A. I. Kotel'nikov, A. P. Pivovarov, A. P. Sadkov, and A. A. Kost, Bioorgan. Khim.,1, 1207 (1975).
I. A. Kozlov, M. V. Shalamberidze, I. Yu. Novikova, N. I. Sokolova, and Z. A. Shabarova, Biokhimiya,42, 1704 (1977).
G. Dreyfuss, K. Schwartz, E. R. Blout, J. R. Barrio, F.-T. Lin, and N. J. Leonard, Proc. Natl. Acad. Sci. USA,75, 1199 (1978).
J. J. Villafranca, S. G. Rhee, and P. B. Chock, Proc. Natl. Acad. Sci. USA,75, 1255 (1978).
N. J. Leonard, J. R. Barrio, and J. A. Secrist III, Biochem. Biophys. Acta,269, 531 (1972).
G. Avigad and S. Damle, Anal. Biochem.,50, 321 (1972).
K. Kimura, M. Nakanishi, T. Yamamoto, and M. Tuboi, Nucleic Acids Res. Special Publ., No. 2, 125 (1976).
A. P. Razzhivin (Razjivin), R. K. Ledneva, G. V. Terganova, A. Yu. Borisov, A. A. Bogdanovand A. A. Kost, Bioorg. Khim.,5, 691 (1979).
R. K. Ledneva, A. P. Razzhivin (Razjivin), A. A. Bogdanov, A. A. Kost, and I. V. Zlatkin, Bioorg. Khim.,5, 701 (1979).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 291–305, March, 1980.
Rights and permissions
About this article
Cite this article
Kost, A.A., Ivanov, M.V. Etheno derivatives of adenine and cytosine (review). Chem Heterocycl Compd 16, 209–221 (1980). https://doi.org/10.1007/BF00553878
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00553878