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
-
Letter: Phosphite coupling procedure for generating internucleotide links.
J Am Chem Soc. 1975 May 28;97(11):3278-9
PMID: 1133350
-
Synthesis of thymidine oligonucleotides by phosphite triester intermediates.
J Am Chem Soc. 1976 Jun 9;98(12):3655-61
PMID: 1270704
-
High-pressure liquid chromatography in polynucleotide synthesis.
Biochemistry. 1978 Apr 4;17(7):1257-67
PMID: 656387
-
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
-
Sequencing end-labeled DNA with base-specific chemical cleavages.
Methods Enzymol. 1980;65(1):499-560
PMID: 6246368
-
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
-
Synthesis of oligodeoxyribonucleotides on silica gel support.
Nucleic Acids Res. 1981 Jun 25;9(12):2807-17
PMID: 6269061
-
Automated synthesis of gene fragments.
Science. 1981 Oct 16;214(4518):270-4
PMID: 6169150
-
Synthesis of mixed oligodeoxyribonucleotides following the solid phase method.
Nucleic Acids Res. 1982 May 25;10(10):3291-301
PMID: 7099964
-
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
-
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
-
Improvements in the phosphoramidite procedure for the synthesis of oligodeoxyribonucleotides.
Nucleic Acids Res. 1983 May 11;11(9):2575-84
PMID: 6856470