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A rapid synthesis of a DNA fragment using an unprotected nucleoside and a phosphine derivative

Shimidzu, T.; Maikuma, S.; Yamana, K.; Yamoto, S.; Honda, K.

Nucleic Acids Symposium Series 16: 149-152

1985

ISSN/ISBN: 0261-3166
PMID: 4088860
Document Number: 250907
A rapid synthesis of DNA fragment from unprotected nucleoside and phosphine derivative, morpholinophosphordichloridite, has been studied, demonstrating a d(T-T) and its amino-phosphonate derivative syntheses. A high selectivity of this reagent eliminates the protection of nucleoside hydroxyl groups. The P-N bond in the resulting dinucleoside phosphite can readily be converted to a phosphite triester with alcohol and to the corresponding aminophosphonate by a non-aqueous oxidation with m-chlorobenzoic acid. The P-N bond in the phosphate link is very stable and so provides a protection for the phosphoryl group which has many potential uses. Deprotection can be achieved by a simple treatment with NH2OH.

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Mcelhinney, R.S.; Mccormick, J.E.; Bibby, M.C.; Double, J.A.; Atassi, G.; Dumont, P.; Pratesi, G.; Radacic, M. 1989: Nucleoside analogues. 9. Seco-nucleoside analogues of some 5-fluorouracil/nitrosourea molecular combinations having uracil as base: synthesis and anti-tumour activity Anti-Cancer Drug Design 4(3): 191-207
Goodman, M.G.; Weigle, W.O. 1982: Induction of immunoglobulin secretion by a simple nucleoside derivative Journal of Immunology 128(6): 2399-2404
Khalikov, S.Kh.; Ismoilov, M.I.; Shakhmatov, A.N. 1990: Synthesis of a 17-member peptide (143-159)--the VP(1) fragment of A(12) foot-and-mouth disease virus. I. Synthesis of fragments (143-145), (146-148), 149-152), (153-155), and (156-159) Bioorganicheskaia Khimiia 16(11): 1477-1487
Khropov, I.V.; Guliaev, N.N.; Severin, E.S. 1977: A new method for synthesis of some nucleoside 5'-phosphonate esters Biokhimiia 42(10): 1742-1746
Shirokova, E.A.; Shipitsyn, A.V.; Kuznetsova, E.V.; Viktorova, L.S.; Kraevskiĭ, A.A. 1993: 5'-S-nucleoside triphosphates. Synthesis and substrate properties in tests with DNA polymerases Bioorganicheskaia Khimiia 19(12): 1226-1233
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Antrazhev, A.M.; Diatkina, N.B.; Kraevskiĭ, A.A.; Kukhanova, M.K.; Chidzhavadze, Z.G. 1987: Ability of 3'-substituted nucleoside phosphothioates to terminate DNA synthesis catalyzed by various DNA-polymerases Bioorganicheskaia Khimiia 13(8): 1045-1052
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Hänsicke, A.; Krause, E.; Bienert, M.; Schmidt, M.; Kobert, S.; Schellenberger, V.; Jakubke, H.D.; Kaufmann, K.D. 1991: Chymotrypsin-catalyzed fragment coupling synthesis of GnRH-analogs Biomedica Biochimica Acta 50(10-11): S201-S204
Kilesso, T.I.; Shobukhov, V.M.; Papchikhin, A.V.; Galegov, G.A. 1987: Inhibitory effect of various analogs of nucleoside-5'-triphosphates on DNA synthesis catalyzed by DNA polymerase from herpes simplex virus type i Molekuliarnaia Genetika Mikrobiologiia i Virusologiia 10: 41-44
Kitamura, M.; Nimura, A.; Kunimoto, K.; Segawa, H.; Shimidzu, T. 1991: Synthesis and properties of oligonucleotide derivative with P(V) porphyrin Nucleic Acids Symposium Series 25: 13-14
Pal'keeva, M.E.; Sidorova, M.V.; Molokoedov, A.S.; Kuznetsova, T.V.; Tishchenko, V.A.; Kobylianskiĭ, A.G.; Bespalova, Z.D.; Nasonov, E.L.; Evstigneeva, R.P. 1998: Synthesis and biological properties of artificial antigens based on 280-289 fragment of beta2-gpi Bioorganicheskaia Khimiia 24(7): 502-508
Engel, J.; von Schlichtegroll, A.; Sheldrick, W.S. 1982: Synthesis and absolute configuration of a tinofedrine-oxazolidine derivative Arzneimittel-Forschung 32(5): 475-477
Efimov, V.A.; Buriakova, A.A.; Polushin, N.N.; Pashkova, I.N.; Dmitrakova, E.V. 1989: Synthesis and expression of an artificial gene of an IgG-binding fragment of protein A from Staphylococcus aureus Bioorganicheskaia Khimiia 15(4): 499-507
Semenov, A.N.; Lomonosova, I.V. 1993: Synthesis of a partially purified fragment of salmon calcitonin 1-16 using a phenylhydrazide protective group Bioorganicheskaia Khimiia 19(2): 182-189