Photocleavable Protecting Groups as Nucleobase Protections Allowed the Solid-Phase Synthesis of Base-Sensitive SATE-Prooligonucleotides
1999; American Chemical Society; Volume: 64; Issue: 17 Linguagem: Inglês
10.1021/jo990479h
ISSN1520-6904
AutoresKarine Alvarez, Jean‐Jacques Vasseur, Thierry Beltran, Jean‐Louis Imbach,
Tópico(s)Click Chemistry and Applications
ResumoThe first synthesis of oligodeoxynucleotide heteropolymers carrying base-sensitive S-pivaloylthioethyl (t-Bu-SATE) phosphotriester linkages has been performed. It is based on the use of 6-nitroveratryloxycarbonyl (NVOC) and 2,2'-bis(2-nitrophenyl)ethoxycarbonyl (diNPEOC) groups as nucleobase protections in combination with photolysis deprotection. The synthesis was realized using the phosphoramidite approach on solid support bearing a 1-(o-nitrophenyl)-1,3-propanediol linker. The removal of the protecting groups and the cleavage of the oligonucleotides from the solid support were accomplished in a single photolysis procedure upon UV irradiation at wavelengths >300 nm. Faster deprotection rates were observed for diNPEOC-protected nucleosides and oligomers than with NVOC-protected ones. The synthesis of pentanucleoside t-Bu-SATE-phosphotriesters d(5'TpCpCpCpTp3'), d(5'TpApApApAp3'), and d(5'TpGpGpGpTp3') and of dodecanucleoside t-Bu-SATE-phosphotriesters and -phosphorothioate d(5'ApCpApCpCpCpApApTpTpCpTp3') and d(5'ApGpApApTpTpGpGpGpTpGpTp3') demonstrated the efficiency of the method.
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