Nucleic Acids Research, 1984, Vol. 12, No. 11 4539-4557
© 1984
CHEMISTRY |
Polymer support oligonucleotide synthesis XVIII1.2): use of ß-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product
Institut für Organische Chemie und Biochemie, Universität Hamburg Martin-Luther-King-Platz 6, D-2000 Hamburg 13, FRG
Received February 9, 1984. Revised April 10, 1984. Accepted May 9, 1984.
Various 5'-0-N-protected deoxynucleoside-3'-0-ß-cyanoethyl-N,N-dialkylamino-/N-morpholinophosphoramidites were prepared from ß-cyanoethyl monochlorophosphoramidites of N,N-dimethylamine, N,N-diisopropylamine and N-morpholine. These active deoxynucleoside phosphites have successfully been used for oligodeoxy-nucleotide synthessis on controlled pore glass as polymer support and are very suitable for automated DNA-synthesis due to their stability in solution. The intermediate dichloro-ß-cyanoethoxy-phosphine can easily be prepared free from any PCl3 contamination. The active monomers obtained from ß-cyanoethyl monochloro N,N-diisopropylaminophosphoramidites are favoured. Cleavage of the oligonucleotide chain from the polymer support, N-deacylation and deprotection of ß-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.
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