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Synlett
DOI: 10.1055/a-2322-3741
letter

Evaluation of Transiently O-6 Protected Guanosine Morpholino Nucleosides in PMO Synthesis

Md Qasim
1   School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata, India (Ringgold ID: RIN62397)
,
Atanu Ghosh
1   School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata, India (Ringgold ID: RIN62397)
,
Arnab Das
1   School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata, India (Ringgold ID: RIN62397)
,
Surajit Sinha
1   School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata, India (Ringgold ID: RIN62397)
› Author AffiliationsSupported by: Department of Science and Technology New Delhi DST/TDT/TC/RARE/2022/10c2
Supported by: Science and Engineering Research Board TTR/2021/000044
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Here we present a novel strategy to synthesize O-6 protected morpholino guanosine monomers by trimethylsilylethyl group, 1-(4-azido-phenyl) ethan-1-ol and para methoxy benzyl alcohol, respectively. The introduction of this protecting group increases the solubility of the morpholino nucleoside which is crucial during PMO synthesis. HPLC analysis shows trimethylsilylethyl protected monomer gives better coupling efficiency in PMO synthesis compared to regular one. Moreover the nonpolar nature of the O-6 protected monomer facilitated the guanosine rich PMO block in solution.



Publication History

Received: 26 February 2024

Accepted: 08 May 2024

Accepted Manuscript online:
08 May 2024

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