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PMID: 6547529 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

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 research ·Vol. 12 ·No. 11 ·1984-06-11 ·Pages 4539-57

Sinha ND, Biernat J, McManus J, Köster H

Abstract

Various 5'O-N-protected deoxynucleoside-3'-O-beta-cyanoethyl-N,N-dialkylamino-/N- morpholinophosphoramidites were prepared from beta-cyanoethyl monochlorophosphoramidites of N,N-dimethylamine, N,N-diisopropylamine and N-morpholine. These active deoxynucleoside phosphates have successfully been used for oligodeoxynucleotide synthesis on controlled pore glass as polymer support and are very suitable for automated DNA-synthesis due to their stability in solution. The intermediate dichloro-beta- cyanoethoxyphosphine can easily be prepared free from any PC1(3) contamination. The active monomers obtained from beta-cyanoethyl monochloro N,N- diisopropylaminophosphoramidites are favoured. Cleavage of the oligonucleotide chain from the polymer support, N-deacylation and deprotection of beta-cyanoethyl group from the phosphate triester moiety can be performed in one step with concentrated aqueous ammonia. Mixed oligodeoxynucleotides are characterized by the sequencing method of Maxam and Gilbert.

MeSH Terms
DNA/chemical synthesis Dimethylamines Indicators and Reagents Magnetic Resonance Spectroscopy Morpholines Oligodeoxyribonucleotides/chemical synthesis,isolation & purification Oligonucleotides/chemical synthesis Organophosphorus Compounds Polymers Propylamines
Chemicals
Dimethylamines Indicators and Reagents Morpholines Oligodeoxyribonucleotides Oligonucleotides Organophosphorus Compounds Polymers Propylamines beta-cyanoethyl phosphorodichloridite morpholine DNA dimethylamine diisopropylamine
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Sinha N D
Biernat J
McManus J
Köster H
References (12)
12 references, click to expand
  1. Letter: Phosphite coupling procedure for generating internucleotide links.
    J Am Chem Soc. 1975 May 28;97(11):3278-9 PMID: 1133350
  2. Synthesis of thymidine oligonucleotides by phosphite triester intermediates.
    J Am Chem Soc. 1976 Jun 9;98(12):3655-61 PMID: 1270704
  3. High-pressure liquid chromatography in polynucleotide synthesis.
    Biochemistry. 1978 Apr 4;17(7):1257-67 PMID: 656387
  4. DNA chain length markers and the influence of base composition on electrophoretic mobility of oligodeoxyribonucleotides in polyacrylamide-gels.
    Nucleic Acids Res. 1979;6(6):2069-87 PMID: 461182
  5. Sequencing end-labeled DNA with base-specific chemical cleavages.
    Methods Enzymol. 1980;65(1):499-560 PMID: 6246368
  6. Rapid synthesis of oligodeoxyribonucleotides. V. Further studies in solid phase synthesis of oligodeoxyribonucleotides through phosphotriester intermediates.
    Nucleic Acids Symp Ser. 1980;(7):243-57 PMID: 7255172
  7. Synthesis of oligodeoxyribonucleotides on silica gel support.
    Nucleic Acids Res. 1981 Jun 25;9(12):2807-17 PMID: 6269061
  8. Automated synthesis of gene fragments.
    Science. 1981 Oct 16;214(4518):270-4 PMID: 6169150
  9. Synthesis of mixed oligodeoxyribonucleotides following the solid phase method.
    Nucleic Acids Res. 1982 May 25;10(10):3291-301 PMID: 7099964
  10. Solid phase synthesis of polynucleotides. VIII. Synthesis of mixed oligodeoxyribonucleotides by the phosphotriester solid phase method.
    Nucleic Acids Res. 1983 Jan 25;11(2):477-88 PMID: 6828376
  11. Further improvements on the phosphotriester synthesis of deoxyribooligonucleotides and the oligonucleotide directed site-specific mutagenesis of E. coli lipoprotein gene.
    Nucleic Acids Res. 1983 May 25;11(10):3227-39 PMID: 6344008
  12. Improvements in the phosphoramidite procedure for the synthesis of oligodeoxyribonucleotides.
    Nucleic Acids Res. 1983 May 11;11(9):2575-84 PMID: 6856470
Article Info
Journal
Nucleic acids research
Abbr.
Nucleic Acids Res
ISSN
0305-1048
Published
1984-06-11
Pages
4539-57
Language
English
Region
England
NLM ID
0411011
PMCID
PMC318857
Subset
IM
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