Details

Autor(en) / Beteiligte

• Seio, Kohji
• Shiraishi, Miyuki
• Utagawa, Eri
• Ohkubo, Akihiro
• Sekine, Mitsuo

Titel

Synthesis of oligodeoxynucleotides using the oxidatively cleavable 4-methoxytritylthio (MMTrS) group for protection of the 5′-hydroxyl groupThis article is part of a themed issue on Biophosphates.Electronic supplementary information (ESI) available: Further experimental data. See DOI: 10.1039/b9nj00678h

Erscheinungsjahr

2010-05

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• We examined the synthesis of oligodeoxynucleotides containing all four nucleobases using the 4-methoxytritylthio (MMTrS) group for protection of the 5′-hydroxyl group. The MMTrS group could be introduced into 3′- O -TBDMS-deoxycytidine, -deoxyadenosine and -deoxyguanosine with the appropriate base protecting groups using strong bases such as n -butyl lithium and lithium hexamethyldisilazide. Because the MMTrS group could be removed by oxidation with an aqueous I 2 solution, the oxidation of internucleotidic phosphite intermediates could be performed simultaneously. Thus, the nucleotide chain could be extended in a three-step protocol that comprised coupling, capping and oxidation/deprotection. Oligodeoxynucleotides with 10 and 20 mixed-base sequences could be synthesized using this protocol. Oligodeoxynucleotides were synthesized without any acid treatment by using the oxidatively-cleavable MMTrS group.