Biopolym. Cell. 1992; 8(1):82-88.
Structure and Function of Biopolymers
A study of side-reactions in H-phosphonate DNA fragments synthesis
- Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine
1, Murmans'ka Str., Kyiv, Ukraine, 02094
Abstract
Possibe side-reactions during the internucleotide condensation in H-phosphonate oligonucleotide synthesis, such as OH-component and P–H bonds acylatiorr and base modification, and their kinetics in presence of some bases have been studied. Stable modifications of heterocyclic bases by pivaloyl chloride were observed. It has been shown that P–H bonds acylation leads to oligonucleotide chain cleavage at acylated sites. The side-reactions rates were found to be several times lower in quinoline than in more basic pyridine.
Full text: (PDF, in Russian)
References
[1]
Itakura K, Rossi JJ, Wallace RB. Synthesis and use of synthetic oligonucleotides. Annu Rev Biochem. 1984;53:323-56.
[2]
Ellis RW. The applications of synthetic oligonucleotides to molecular biology. Pharm Res. 1986;3(4):195-207.
[3]
Garegg PJ, Lindh I, Regberg T, Stawinski J, Strömberg R, Henrichson C. Nucleoside H-phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach. Tetrahedron Lett. 1986;27(34):4051–4.
[4]
Froehler BC, Ng PG, Matteucci MD. Synthesis of DNA via deoxynucleoside H-phosphonate intermediates. Nucleic Acids Res. 1986;14(13):5399-407.
[5]
Regberg T, Stawinski J, Ströberg R. Nucleoside h-phosphonates. IX. Possible side-reactions during hydrogen phosphonate diester formation. Nucleosides Nucleotides. 1988;7(1):23–35.
[6]
Kuyl-Yeheskiely E, Spierenburg M, van der Elst H et al. Reaction of pivaloyl chloride with internucleotidic H-phosphonate diesters. Reel. Trav. Chim. Pays-Bas. 1986.1-105(11): 505-506.
[7]
Oligonucleotide synthesis: a practical approach. Ed. M. J. Gait. Oxford; Washington DS: IRL press, 1985. 218 p.
[8]
Kalashnikov VV, Samukov VV, Shubina TN, Yamshchikov VF. Application of the reverse-phase chromatography in oligonucleotide synthesis. Bioorg Khim. 1983, 9(5):666-72.
[9]
Efimov VA, DubeÄ IIa. Modification of H-phosphonate method of oligonucleotide synthesis on polymer support. Bioorg Khim. 1990;16(2):211-8.
[10]
Dubey IYa, Lyapina TV, Fedoryak DM. An efficient variant of the solid phase H-phosphonate synthesis of oligodeoxyribonucleotides. Bioorg Khim. 1990; 16(11):1574-76
[11]
Efimov VA, Dubey IY, Chakhmakhcheva OG. NMR Study and Improvement of H-Phosphonate Oligonucleotide Synthesis. Nucleosides Nucleotides. 1990;9(3):473–7.
[12]
Andrus A, Efcavitch JW, McBride LJ, Giusti B. Novel activating and capping reagents for improved hydrogen-phosphonate DNA synthesis. Tetrahedron Let. 1988;29(8):861–4.
[13]
Reese CB, Skone PA. The protection of thymine and guanine residues in oligodeoxyribonucleotide synthesis. J Chem Soc Perkin 1. 1984;1263-71.
[14]
Adamiak RW, Biała E, Skalski B. New, ionic side-products in oligonucleotide synthesis: formation and reactivity of fluorescent N-/purin-6-yl/pyridinium salts. Nucleic Acids Res. 1985;13(8):2989-3003.
[15]
Batchikova NV, Skaptsova NV, Tvardovskaia SE, BesidskiÄ ES, Dan'kov IuV. Chemical synthesis and cloning of the human epidermal growth factor gene. Bioorg Khim. 1988;14(5):621-30.
[16]
Kamimura T, Tsuchiya M, Koura K, Sekine M, Hata T. Diphenylcarbamoyl and propionyl groups: a new combination of protecting groups for the guanine residue. Tetrahedron Lett. 1983;24(27):2775–8.
[17]
De Vroom E, Spierenburg ML, Dreef CE, van der Marel GA, van Boom JH. A general procedure to convert H-phosphonate mono- or diesters of nucleic acids into valuable phosphate di- or triesters. Recl Trav Chim Pays Bas 1987;106(2):65–6.
[18]
Sekine M, Satoh M, Yamagata H, Hata T. Acylphosphonates: phosphorus-carbon bond cleavage of dialkyl acylphosphonates by means of amines. Substituent and solvent effects for acylation of amines. J Org Chem. 1980;45(21):4162–7.
[19]
Kume A, Fujii M, Sekine M, Hata T. Acylphosphonates. 4. Synthesis of dithymidine phosphonate. A new method for generation of phosphonate function via aroylphosphonate intermediates. J Org Chem. 1984;49(12):2139–43.