Solid-phase Synthesis of Branched Oligoribonucleotides Related to Messenger RNA Splicing Intermediates

Overview

Journal Nucleic Acids Res

Publisher Oxford University Press

Specialty Biochemistry

Date 1992 Dec 25

PMID 1480476

Citations 16

Authors

M J Damha

K Ganeshan

R H Hudson

S V Zabarylo

Affiliations

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Abstract

The chemical synthesis of oligoribonucleotides containing vicinal (2'-5')- and (3'-5')-phosphodiester linkages is described. The solid-phase method, based on silyl-phosphoramidite chemistry, was applied to the synthesis of a series of branched RNA [(Xp)nA2' (pN)n3'(pN)n] related to the splicing intermediates derived from Saccharomyces cerevisiae rp51a pre-messenger RNA. The branched oligonucleotides have been thoroughly characterized by nucleoside and branched nucleotide composition analysis. Branched oligoribonucleotides will be useful in the study of messenger RNA splicing and in determining the biological role of RNA 'lariats' and 'forks' in vivo.

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References

de Rooij J, Burgers P, VAN Boom J . Neighbouring group participation in the unblocking of phosphotriesters of nucleic acids. Nucleic Acids Res. 1979; 6(6):2237-59. PMC: 327848. DOI: 10.1093/nar/6.6.2237. View

Wallace J, Edmonds M . Polyadenylylated nuclear RNA contains branches. Proc Natl Acad Sci U S A. 1983; 80(4):950-4. PMC: 393505. DOI: 10.1073/pnas.80.4.950. View

Scaringe S, Francklyn C, Usman N . Chemical synthesis of biologically active oligoribonucleotides using beta-cyanoethyl protected ribonucleoside phosphoramidites. Nucleic Acids Res. 1990; 18(18):5433-41. PMC: 332221. DOI: 10.1093/nar/18.18.5433. View

Damha M, Giannaris P, Zabarylo S . An improved procedure for derivatization of controlled-pore glass beads for solid-phase oligonucleotide synthesis. Nucleic Acids Res. 1990; 18(13):3813-21. PMC: 331081. DOI: 10.1093/nar/18.13.3813. View

Kierzek R, Kopp D, Edmonds M, Caruthers M . Chemical synthesis of branched RNA. Nucleic Acids Res. 1986; 14(12):4751-64. PMC: 311489. DOI: 10.1093/nar/14.12.4751. View

Damha M, Ogilvie K . Conformational properties of branched RNA fragments in aqueous solution. Biochemistry. 1988; 27(17):6403-16. DOI: 10.1021/bi00417a032. View

Laird P . Trans splicing in trypanosomes--archaism or adaptation?. Trends Genet. 1989; 5(7):204-8. PMC: 7134362. DOI: 10.1016/0168-9525(89)90082-6. View

Wu T, Ogilvie K, Pon R . Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides. Nucleic Acids Res. 1989; 17(9):3501-17. PMC: 317792. DOI: 10.1093/nar/17.9.3501. View

Hartmuth K, Barta A . Unusual branch point selection in processing of human growth hormone pre-mRNA. Mol Cell Biol. 1988; 8(5):2011-20. PMC: 363380. DOI: 10.1128/mcb.8.5.2011-2020.1988. View

10.

Vijayraghavan U, Parker R, TAMM J, Iimura Y, Rossi J, Abelson J . Mutations in conserved intron sequences affect multiple steps in the yeast splicing pathway, particularly assembly of the spliceosome. EMBO J. 1986; 5(7):1683-95. PMC: 1166995. DOI: 10.1002/j.1460-2075.1986.tb04412.x. View

11.

Pon R, Usman N, Ogilvie K . Derivatization of controlled pore glass beads for solid phase oligonucleotide synthesis. Biotechniques. 1988; 6(8):768-75. View

12.

Ogilvie K, Usman N, Nicoghosian K, Cedergren R . Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity. Proc Natl Acad Sci U S A. 1988; 85(16):5764-8. PMC: 281845. DOI: 10.1073/pnas.85.16.5764. View

13.

Fouser L, Friesen J . Mutations in a yeast intron demonstrate the importance of specific conserved nucleotides for the two stages of nuclear mRNA splicing. Cell. 1986; 45(1):81-93. DOI: 10.1016/0092-8674(86)90540-4. View

14.

Sharp P . Splicing of messenger RNA precursors. Science. 1987; 235(4790):766-71. DOI: 10.1126/science.3544217. View

15.

HORNIG H, Aebi M, Weissmann C . Effect of mutations at the lariat branch acceptor site on beta-globin pre-mRNA splicing in vitro. Nature. 1986; 324(6097):589-91. DOI: 10.1038/324589a0. View

16.

Pon R, Usman N, Damha M, Ogilvie K . Prevention of guanine modification and chain cleavage during the solid phase synthesis of oligonucleotides using phosphoramidite derivatives. Nucleic Acids Res. 1986; 14(16):6453-70. PMC: 311657. DOI: 10.1093/nar/14.16.6453. View

17.

Reese C, Skone P . Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions. Nucleic Acids Res. 1985; 13(14):5215-31. PMC: 321860. DOI: 10.1093/nar/13.14.5215. View

18.

REED R, Maniatis T . Intron sequences involved in lariat formation during pre-mRNA splicing. Cell. 1985; 41(1):95-105. DOI: 10.1016/0092-8674(85)90064-9. View

19.

Pon R, Damha M, Ogilvie K . Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides. Nucleic Acids Res. 1985; 13(18):6447-65. PMC: 321970. DOI: 10.1093/nar/13.18.6447. View

20.

Sund C, Foldesi A, Yamakage S, Chattopadhyaya J . Synthesis of branched nona and deca-RNA modelling the lariat formed in pre-mRNA processing reaction (splicing). Nucleic Acids Symp Ser. 1991; (24):9-12. View