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OPTIMIZATION OF SOLID-PHASE SYNTHESIS OF POLYAMIDE NUCLEIC ACID MIMETICS WITH APPLICATION OF MALDI-TOF MASS-SPECTROMETRY

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Abstract

The solid-phase synthesis of a tetrameric model sequence of polyamide nucleic acid mimetics (PANAM) incorporating terminal chiral and charged unit was performed. As a result during the synthesis and cleavage from the resin the tendency of PANAM with the N-terminal negatively charged monomer to cyclization with simultaneous N-acyl transfer of carboxyethyl base residue was found. Application of MALDI-TOF mass - spectrometry allowed us to find suitable conditions for obtaining PANAM oligomers without the significant amount of by-products.

About the Authors

M. V. Shirayeva
M.V. Lomonosov Moscow State University of Fine Chemical Technology
Russian Federation


Yu. G. Kirillova
M.V. Lomonosov Moscow State University of Fine Chemical Technology
Russian Federation


E. D. Nikol’Skaya
M.V. Lomonosov Moscow State University of Fine Chemical Technology
Russian Federation


D. I. Prokhorov
M.V. Lomonosov Moscow State University of Fine Chemical Technology
Russian Federation


I. P. Smirnov
Scientific Research Institute of Physical and Chemical Medicine
Russian Federation


G. E. Pozmogova
Scientific Research Institute of Physical and Chemical Medicine
Russian Federation


References

1. Lebedeva I., Stein C.A. Antisense oligonucleotides: Promise and reality // Annu. Rev. Pharmacol. Toxicol. 2001. V. 41. P. 403–419.

2. Mansoor M., Melendez A.J. Advances in antisense oligonucleotide development for target identification, validation, and as novel therapeutics // Gene Regulation & Systems Biology. 2008. V. 2. P. 275–295.

3. Nielsen P.E., Egholm M., Berg R.H., Buchardt O. Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide // Science. 1991. V. 254. P. 1497–1500.

4. Demidov V.V. New kids on the block: Emerging PNA-based DNA diagnostics // Expert Rev. Mol. Diagn. 2002. V. 2. P. 199–201.

5. Brandt O., Hoheisel J.D. Peptide nucleic acids on microarrays and other biosensors // Trends in Biotechnology. 2004. V. 22. P. 617–622.

6. Brandt O., Feldner J., Stephan A., Schroder M., Schnolzer M., Arlinghaus H.F., Hoheisel J.D., Jacob A. PNA microarrays for hybridisation of unlabelled DNA samples // Nucl. Acids Res. 2003. V. 31. №. 19. P. 119.

7. Orum H, Nielsen P.E., Jorgensen M., Larsson C., Stanley C., Koch T. Sequence-specific purification of nucleic acids by PNA-controlled hybrid selection // BioTechnique. 1995. V. 19. P. 472–480.

8. Kuhn H., Hu Y., Frank-Kamenetskii M.D., Demidov V.V. Artificial site-specific DNA-nicking system based on common restriction enzymes assisted by PNA openers // Biochemistry. 2003. V. 42. P. 4985–4992.

9. Tanemura K., Ogura A., Cheong C., Gotoh H., Matsumoto K., Sato E., Hayashi Y., Lee H., Kondo T. Dynamic rearrangement of telomeres during spermatogenesis in mice // Developmental. 2005. V. 281. P. 196–207.

10. Nielsen P.E. Structural and biological properties of peptide nucleic acid (PNA) // Pure Appl. Chem. 1998. V. 70. P. 105–110.

11. Betts L., Josey J.A., Veal J.M., Jordan S.R. A nucleic acid triple helix formed by a peptide nucleic acid–DNA complex // Science. 1995. V. 270. P. 1838–1841.

12. Wittung P., Eriksson M., Lyng R., Nielsen P. E. Induced chirality in PNA-PNA duplexes // J. Am. Chem. Soc. 1995 V. 41. P. 10167–10173.

13. Sforza S., Haaima G., Marchelli R., Nielsen P.E. Chiral peptide nucleic acids (PNAs): Helix handedness and DNA recognition // Eur. J. Org. Chem. 1999. P. 197–204.

14. Haaima G., Loshe A., Buchardt O., Nielsen P.E. Peptide nucleic acids (PNAs) containing thymine monomers derived from chiral amino acids: hybridization and solubility properties of D-lysine PNA // Angew. Chem. Int. Ed. Engl. 1996. V. 35. P. 1939–1942.

15. Dragulescu-Andrasi A., Rapireddy S., Frezza B. M., Gayathri C., Gil R. R., Ly D.H. Cell-permeable peptide nucleic acid designed to bind to the 5′-untranslated region of E-cadherin transcript induces potent and sequence-specific antisense effects // J. Am. Chem. Soc. 2006. V. 128. P. 10258–10267.

16. Боярская Н.П., Кириллова Ю. Г., Есипов Д.С., Швец В.И. Твердофазный синтез декамера отрицательно заряженных ПАНКМ с псевдопептидной связью GlyΨL-Glu // Вестник МИТХТ. 2007. Т. 2. № 5. С. 33–36.

17. Christensen L., Fitzpatrick R., Gildea B., Petersen K.H., Hansen H.F., Koch T., Egholm M., Buchardt O., Nielsen P.E. Solid-phase synthesis of peptide nucleic acids // J. Peptide Sci. 1995. V. 1. P. 185–183.

18. Dueholm K.L., Egholm M., Behrens C., Cristensen L., Hansen H.F., Vulpius T., Petersen K.H., Berg R.H., Nielsen P.E., Buchardt O. Synthesis of Peptide Nucleic Acid monomers containing the four natural nucleobases: Thymine, cytosine, adenine, and guanine and their oligomerization // J. Org. Chem. 1994. V. 59. P. 5767–5773.

19. Баранов А.В., Цвид Н.С., Лукьянченко В.И., Прохоров Д.И., Кириллова Ю.Г., Швец В.И. Исследование путей синтеза цитозинового мономера отрицательно заряженных пептидно-нуклеиновых кислот // Вестник МИТХТ. 2007. Т. 2. № 5. С. 28–32.

20. Ширяева М.В., Кириллова Ю.Г., Есипова О.В., Еремин С.В., Лукьянова Т.А., Швец В.И. Твердофазный синтез отрицательно заряженных олигомеров полиамидных миметиков нуклеиновых кислот // Вестник МИТХТ. 2011. Т. 6. № 2. С. 81–85.

21. Upert G., Mehiri M., Goddard M.-L., Di Giorgio A., Benhida R., Condom R., Patino N. The “fully protected backbone” approach as a versatile tool for a new solid-phase PNA synthesis strategy // Tetrahedron Lett. 2005. V. 46. P. 4081–4085.

22. Amant A.H.St., Hudson R.H.E. Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine // Org. Biomol. Chem. 2012. V. 10. P. 876–881.

23. Гершкович А.А., Кибирев В.К. Химический синтез пептидов. Киев: Наукова думка. 1992. 360 с.

24. Eriksson M, Christensen L, Schmidt J, Haaima G, Orgel L, Nielsen P.E. Sequence dependent N-terminal rearrangement and degradation of peptide nucleic acid (PNA) in aqueous solution // Nouv. J. Chim. 1998. V. 22. P. 1055–1059.

25. Прохоров Д.И., Кириллова Ю.Г., Боярская Н.П., Тевяшова А.Н., Есипова О.В., Звонкова Е.Н., Швец В.И. Синтез тиминсодержащего мономера отрицательно заряженных ПНК // Хим.-фарм. журн. 2005. Т. 39. № 6. С. 39–43.

26. Boyarskaya N.P., Prokhorov D.I., Kirillova Yu.G., Zvonkova E.N., Shvets V.I. Synthesis of protected pseudopeptides from dicarboxylic aminoacids by Mitsunobu condensation // Tetrahedron Lett. 2005. V.46. № 43. P. 7359–7362.


For citation:


Shirayeva M.V., Kirillova Yu.G., Nikol’Skaya E.D., Prokhorov D.I., Smirnov I.P., Pozmogova G.E. OPTIMIZATION OF SOLID-PHASE SYNTHESIS OF POLYAMIDE NUCLEIC ACID MIMETICS WITH APPLICATION OF MALDI-TOF MASS-SPECTROMETRY. Fine Chemical Technologies. 2013;8(1):87-95. (In Russ.)

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