Biopolym. Cell. 1988; 4(6):298-302.
http://dx.doi.org/10.7124/bc.00023C
Cell Biology
Substrate specificity of uridine and purine nucleoside phosphorylases of the Escherichia coli whole cells
1Zintchenko A. I., 1Eroshevskaya L. A., 1Barai V. N., 2Mikhailopulo I. A.
  1. Institute of Microbiology, Academy of Sciences of the Byelorussian SSR
    Minsk, USSR
  2. Institute of Bioorganic Chemistry, Academy of Sciences of the Byelorussian SSR
    Minsk, USSR

Abstract

Substrate specificity of uridine and purine nucleoside phosphorylases of the whole cells of Escherichia coli BM-11 has been studied monitoring phosphorolysis of uridine and a series of its analogues modified in the carbohydrate moiety to uracil and pentofuranose-I-phosphate, and synthesis of corresponding adenine nucleosides. Both enzymes reveal similar requirements to the structure and stereochemistry of uracil nucleosides and of the pentofuranose-1-phosphates, respectively, namely: a) modifications at C-3' decrease the substrate activity to a greater extent as compared with the same modifications at C-2'; the order of substrate activity in the case of modifications at C-2' and C-3' is OH> H> NH2> OH-ara (xylo)» 2'(3')-C-methyl; b) substitution of a methyl group for one of the protons at carbon atom of 5'-CH?OH group does not lead to an essential alterations of the substrate activity in such analogues in comparison with the natural substrates — uridine and ribofuranose-1-phosphate, respectively.
Full text: (PDF, in Russian)

References

[1] Suhadolnik R. J. Nucleosides as biological probes. New York: Wiley-Interscience, 1980. 346 p.
[2] Krayevskiy AA, Kukhanova MK. DNA replication in eukaryotes. Results of science and technology. Moscow, VINITI, 1986; 5-164 (Bioorg. khimiya; Vol. 22).
[3] Preobrazhenskaya MP, Mel'nik SYa. Analogs components of nucleic acids - inhibitors of nucleic acid metabolism. Results of science and technology. Moscow, VINITI, 1984; 244 p. (Bioorg. khimiya; Vol. 1).
[4] De Clercq E. Chemotherapeutic approaches to the treatment of the acquired immune deficiency syndrome (AIDS). J Med Chem. 1986;29(9):1561-9.
[5] Kornberg A. DNA synthesis. Moscow, Mir, 1977; 360 p.
[6] Hammer-Jespersen K. Nucleoside catabolism. Metabolism of nucleotides, nucleosides and nucleobases in microorganisms. Ed. K. Hammer-Jespersen. New York; London: Acad, press, 1983:203-258.
[7] Morisawa H, Utagawa T, Miyoshi T, Yoshinaga F, Yamazaki A, Mitsugi K. A new method for the synthesis of some 9-β--arabinofuranosylpurines by a combination of chemical and enzymatic reactions. Tetrahedron Lett. 1980;21(5)479-482.
[8] Krenitsky TA, Koszalka GW, Tuttle JV. Purine nucleoside synthesis, an efficient method employing nucleoside phosphorylases. Biochemistry. 1981;20(12):3615-21.
[9] Utagawa T, Morisawa H, Yoshinaga F, YamazakicA, Mitsugi K, Hirose Y. Enzymatic synthesis of nucleoside antibiotics. Part I. Microbiological synthesis of adenine arabinoside. Agric Biol Chem. 1985; 49(4):1053-8.
[10] Utagawa T, Morisawa H, Yamanaka F, Yamazaki A, Hirose Y. Enzymatic synthesis of nucleoside antibiotics. Part IV. Microbial synthesis of purine 2'-amino-2'-deoxyribosides. Agric Biol Chem. 1985; 49(9):2711-7.
[11] Imazawa M, Eckstein F. Synthesis of 3'-azido-2',3'-dideoxyribofuranosylpurines. J Org Chem. 1978; 43(15):3044-48.
[12] Vorbruggen H. Methods of nucleoside synthesis. Nucleoside analogues. Chemistry, biology and medical applications. New York; London: Plenum press, 1979. V. 26:35-69.
[13] Huang MC, Hatfield K, Roetker AW, Montgomery JA, Blakley RL. Analogs of 2'-deoxyadenosine: facile enzymatic preparation and growth inhibitory effects on human cell lines. Biochem Pharmacol. 1981;30(19):2663-71.
[14] ERoshevskaia LA, Barai VN, Zinchenko AI, Kvasiuk EI, Mikhailopulo IA. Preparative synthesis of the antiviral nucleoside 9-beta-D-arabinofuranosyladenine by using bacterial cells. Antibiot Med Biotekhnol. 1986;31(3):174-8.
[15] Mikhailopulo IA, Kvasyuk EI, Lyakhovets VI et al. Synthesis of kinetin riboside and its 5'-monophosphate by immobilized bacterial cells. Nucl. Acids Symp. Ser. 1984. N 14:291.
[16] Jensen KF, Nygaard P. Purine nucleoside phosphorylase from Escherichia coli and Salmonella typhimurium. Purification and some properties. Eur J Biochem. 1975;51(1):253-65.
[17] Utagawa T, Morisawa H, Yamanaka S, Yamazaki A, Yoshinaga F, Hirose Y. Enzymatic synthesis of nucleoside antibiotics. Part V. Properties of nucleoside phosphorylase from Enterobacter aerogenes. Agric Biol Chem. 1985; 49(11):3239-46.
[18] Mikhailopulo IA, Wiedner H, Cramer F. Substrate specificity of adenosine deaminase: the role of the substituents at the 2'- and 3'-carbons of adenine nucleosides, of their configuration and of the conformation of the furanose ring. Biochem Pharmacol. 1981;30(9):1001-4.