121058-82-0Relevant articles and documents
Methylamine Deprotection Provides Increased Yield of Oligoribonucleotides
Reddy, M. P.,Farooqui, Firdous,Hanna, Naeem B.
, p. 8929 - 8932 (1995)
Use of methylamine or methylamine/ammonium hydroxide as a cleavage and deprotection reagent for the solid phase synthesis of oligoribonucleotides has significantly increased the yield of the full length oligoribonucleotides as compared to the use of conventional ammonium hydroxide/ethanol.
A base-labile group for 2′-OH protection of ribonucleosides: A major challenge for RNA synthesis
Lavergne, Thomas,Bertrand, Jean-Remi,Vasseur, Jean-Jacques,Debart, Francoise
scheme or table, p. 9135 - 9138 (2009/10/01)
A base-labile group for 2'-OH protection of ribonucleosides was investigated. The solid support was dried by blowing argon through a DNA synthesizer and was first treated with 10% anhydrous piperidine in CH 3CN at room temperature for 15 minutes to eliminate cyanoethyl groups from phosphates. The piperidine solution was removed from the column and the solid support was washed with CH3CN. The three ammoniacal eluates were collected in a screw-capped glass vial and were left at room temperature for a further 1.5 hours to completely deprotect nucleobases and 2'-hydroxyl groups. The fully deprotected oligonucleotide was transferred to a 50 mL round-bottomed flask and isopropylamine was added to the solution before evaporation to dryness. It was observed that PivOM method provides highly pure RNA without any additional desalting step.
Reliable chemical synthesis of oligoribonucleotides (RNA) with 2′-O-[(triisopropylsilyl)oxy]methyl(2′-O-tom)-protected phosphoramidites
Pitsch, Stefan,Weiss, Patrick A.,Jenny, Luzi,Stutz, Alfred,Wu, Xiaolin
, p. 3773 - 3795 (2007/10/03)
A method for the introduction of the 2′-O-[(triisopropylsilyl)oxy]methyl (=tom) group into N-acetylated, 5′-O-dimethoxytritylated ribonucleosides is presented. The corresponding 2′-O-tom-protected phosphoramidite building blocks were obtained in pure form and were successfully employed for the routine synthesis of oligoribonucleotides on DNA synthesizers. Under DNA coupling conditions (2.5 min coupling time for a 1.5-μmol synthesis scale) and with 5-(benzylthio)-1H-tetrazole (BTT) as activator, 2′-O-tom-protected phosphoramidites exhibited average coupling yields >99.4%. The combination of N-acetyl and 2′-O-tom protecting groups allowed a reliable and complete two-step deprotection, first with MeNH2 in EtOH/H2O and then with Bu4NF in THF, without concomitant destruction of the product RNA sequences.