Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1989 Sep 25;17(18):7149–7158. doi: 10.1093/nar/17.18.7149

Universal solid supports for the synthesis of oligonucleotides with terminal 3'-phosphates.

W T Markiewicz 1, T K Wyrzykiewicz 1
PMCID: PMC334794  PMID: 2798088

Abstract

The preparation of two types of supports based on controlled pore glass (CPG) is presented. These supports are compatible with established phosphoroamidite chemistry of oligonucleotides synthesis giving rise to an oligonucleotide with terminal 3'-phosphate function during final deprotection. CPG was modified with: (i) methacrylic acid derivatives and 2-mercaptoethanol (1) or (ii) aminoalkylsilane, succinic anhydride and benzidine (2). Support 2 can be also used for the synthesis of partially protected oligonucleotide 3'-phosphates.

Full text

PDF
7149

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bower M., Summers M. F., Kell B., Hoskins J., Zon G., Wilson W. D. Synthesis and characterization of oligodeoxyribonucleotides containing terminal phosphates. NMR, UV spectroscopic and thermodynamic analysis of duplex formation of [d(pGGAATTCC)]2, [d(GGAATTCCp)]2 and [d(pGGAATTCCp)]2. Nucleic Acids Res. 1987 Apr 24;15(8):3531–3547. doi: 10.1093/nar/15.8.3531. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Efimov V. A., Buryakova A. A., Reverdatto S. V., Chakhmakhcheva O. G., Ovchinnikov YuA Rapid synthesis of long-chain deoxyribooligonucleotides by the N-methylimidazolide phosphotriester method. Nucleic Acids Res. 1983 Dec 10;11(23):8369–8387. doi: 10.1093/nar/11.23.8369. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Kraszewski A., Norris K. E. Simple and rapid procedure for synthesis of deoxynucleoside 3'-2-cyanoethyl-N,N-diisopropyl-amino phosphites. Nucleic Acids Symp Ser. 1987;(18):177–180. [PubMed] [Google Scholar]
  4. Nadeau J. G., Singleton C. K., Kelly G. B., Weith H. L., Gough G. R. Use of ribonucleosides as protecting groups in synthesis of polynucleotides with phosphorylated terminals. Biochemistry. 1984 Dec 4;23(25):6153–6159. doi: 10.1021/bi00320a040. [DOI] [PubMed] [Google Scholar]
  5. Nielsen J., Taagaard M., Marugg J. E., van Boom J. H., Dahl O. Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides. Nucleic Acids Res. 1986 Sep 25;14(18):7391–7403. doi: 10.1093/nar/14.18.7391. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. OHTSUKA E., MOON M. W., KHORANA H. G. STUDIES ON POLYNUCLEOTIDES. 43. THE SYNTHESIS OF DEOXRIBOPOLYNUCLEOTIDES CONTAINING REPEATING DINUCLEOTIDE SEQUENCES. J Am Chem Soc. 1965 Jul 5;87:2956–2970. doi: 10.1021/ja01091a028. [DOI] [PubMed] [Google Scholar]
  7. Purmal' A. A., Drutsa V. L., Shabarova Z. A. Novyi tip modifikatsii DNK. Napravlennoe vvedenie 3'-5'-pirofosfatnykh mezhnukleotidnykh sviazei. Bioorg Khim. 1984 Mar;10(3):394–400. [PubMed] [Google Scholar]
  8. Shabarova Z. A., Dolinnaya N. G., Drutsa V. L., Melnikova N. P., Purmal A. A. DNA-like duplexes with repetitions. III. Efficient template-guided chemical polymerization of d(TGGCCAAGCTp). Nucleic Acids Res. 1981 Nov 11;9(21):5747–5761. doi: 10.1093/nar/9.21.5747. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Sinha N. D., Biernat J., McManus J., Köster H. Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucleic Acids Res. 1984 Jun 11;12(11):4539–4557. doi: 10.1093/nar/12.11.4539. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Sokolova N. I., Ashirbekova D. T., Dolinnaia N. G., Shabarova Z. A. Khimicheskie reaktsii v dvuspiral'nykh nukleinovykh kislotakh. IV. Bromtsian--vysokoéffektivnyi reagent pri kondensatsii oligodezoksiribonukleotidov. Bioorg Khim. 1987 Sep;13(9):1286–1288. [PubMed] [Google Scholar]
  11. Sokolova N. I., Ashirbekova D. T., Dolinnaya N. G., Shabarova Z. A. Chemical reactions within DNA duplexes. Cyanogen bromide as an effective oligodeoxyribonucleotide coupling agent. FEBS Lett. 1988 May 9;232(1):153–155. doi: 10.1016/0014-5793(88)80406-x. [DOI] [PubMed] [Google Scholar]
  12. Volkov E. M., Romanova E. A., Krug A., Oretskaia T. S., Potapov V. K. Avtomticheskii sintez oligodezoksiribonukleotidov s kontsevymi fosfatnymi gruppami. Bioorg Khim. 1988 Aug;14(8):1034–1039. [PubMed] [Google Scholar]
  13. van Boom J. H., Burgers P. M., Haasnoot C. A. Synthesis of 3'-phosphates of diribonucleoside monophosphates via phosphotriester intermediates. Nucleic Acids Res. 1976 Oct;3(10):2731–2747. doi: 10.1093/nar/3.10.2731. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES