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.
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.
D004247:DNA / Q000138:chemical synthesis*; D004123:Dimethylamines; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009025:Morpholines; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000302:isolation & purification; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D011108:Polymers; D011437:Propylamines
D004123:Dimethylamines; D007202:Indicators and Reagents; D009025:Morpholines; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D011108:Polymers; D011437:Propylamines; C041753:beta-cyanoethyl phosphorodichloridite; C037574:morpholine; D004247:DNA; C034516:dimethylamine; C007442:diisopropylamine