An expeditious synthesis of novel DNA nucleobase mimics of (+)-anisomycin.

Umesh K Mishra, Yogesh S Sanghvi, R Abhiraj, Srinivasa-Gopalan Sampathkumar, Namakkal G Ramesh

Carbohydrate research 2022 Oct

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A glycal based expeditious synthesis of novel nucleoside analogues of (+)-anisomycin is reported. Readily available tri-O-benzyl-D-glucal was converted to a partially protected trihydroxypyrrolidine that is used as a common scaffold for the introduction of various nucleobases at the primary hydroxyl centre. Nucleoside analogues possessing all four DNA bases have been synthesized. Selective acetylation at C3 position was carried out with two of these unnatural nucleosides in order to mimic the structure of (+)-anisomycin. Cytotoxicity studies of some of these nucleosides showed that they display weaker activity on HeLa cells than Ara-C. Copyright © 2022 Elsevier Ltd. All rights reserved.

Citation

Umesh K Mishra, Yogesh S Sanghvi, R Abhiraj, Srinivasa-Gopalan Sampathkumar, Namakkal G Ramesh. An expeditious synthesis of novel DNA nucleobase mimics of (+)-anisomycin. Carbohydrate research. 2022 Oct;520:108645