Synthesis of novel C4-linked imidazole ribonucleoside phosphoramidites for probing general acid and base catalysis in ribozyme |
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Authors: | Lisa Araki Maho Yamaguchi Natsumi Taniguchi Zheng-yun Zhao |
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Affiliation: | a Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan b Department of Biochemistry, MSI/WTB Complex, University of Dundee, Dundee DD1 5EH, UK |
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Abstract: | We describe the synthesis of novel C4-linked imidazole ribonucleoside phosphoramidite (PA) 1a by which the imidazole moiety is incorporated into VS ribozyme to study its role in general acid and base catalysis. Investigation of protecting groups for the imidazole-N first indicated that pivaloyloxymethyl (POM) was adequate as an N-protecting group for the imidazole nucleoside, which could be readily removed under mild basic conditions. Further, the synthetic method was extended to synthesis of 2′-deoxy- and 2′-O-allyl nucleoside PAs 1b and 1c. |
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Keywords: | Imidazole Phosphoramidite Ribozyme POM RNA |
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