5864-33-5Relevant academic research and scientific papers
Solid-Phase Oligodeoxynucleotide Synthesis: A Two-Step Cycle Using Peroxy Anion Deprotection
Sierzchala, Agnieszka B.,Dellinger, Douglas J.,Betley, Jason R.,Wyrzykiewicz, Tadeusz K.,Yamada, Christina M.,Caruthers, Marvin H.
, p. 13427 - 13441 (2007/10/03)
A novel solid-phase phosphoramidite based oligodeoxynucleotide two-step synthesis method has been developed. Keys to this method are replacement of the 5′-dimethoxytrityl blocking group with an aryloxycarbonyl and the use of N-dimethoxytrityl protection for the exocyclic amines of adenine and cytosine. With these modifications, coupling of each 2′-deoxynucleoside 3′-phosphoramidite to the growing oligodeoxynucleotide on the solid support can be followed by treatment with an aqueous mixture of peroxy anions buffered at pH 9.6. This reagent effectively removes the carbonate protecting group and simultaneously oxidizes the phosphite internucleotide linkage. As a consequence a new two-step synthesis cycle is possible. Oligodeoxynucleotides synthesized using this approach are identical to authentic samples when tested by a variety of analytical techniques.
Synthesis of purine and pyrimidine 3′-amino-3′-deoxy- and 3′-amino-2′,3′-dideoxyxylonucleosides
Garcia-Alles, Luis F.,Magdalena, Julia,Gotor, Vicente
, p. 6980 - 6986 (2007/10/03)
A general procedure to obtain the 3′-aminoxylonucleosides 13a,b and 17a,b is presented. The synthetic scheme is based on the 5′ directed intramolecular nucleophilic substitution at the 3′-activated position of the nucleoside. The approach of the incoming group to this position takes place regio- and stereoselectively from the most hindered face of the nucleoside. The methodology presented is applicable to ribonucleosides and 2′-deoxyribonucleosides, regardless of their nitrogenated base.
