Formation of N-branched oligonucleotides as by-products in solid-phase oligonucleotide synthesis.
During the synthesis of oligonucleotides by the standard phosphoramidite method using 2'-deoxycytidine- derivatized solid support, a side reaction was observed that gave rise to the formation of high molecular weight N-branched oligomers having two identical chains linked to the 3'-terminal 2'-deoxycytidine. Postsynthesis treatment with neat triethylamine trihydrofluoride selectively cleaved the phosphoramidate linkage and converted the N-branched oligomers back to the expected oligonucleotides.
Cazenave
Christian
C
INSERM U386; Université Victor Segalen-Bordeaux 2, 33076 Bordeaux Cedex, France.
Bathany
Katell
K
Rayner
Bernard
B
D001483:Base Sequence; D003841:Deoxycytidine / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011073:Polyamines / Q000737:chemistry*
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D011073:Polyamines; C434331:phosphoramidite; C005391:diethylenetriamine; D003841:Deoxycytidine