An efficient protection-free chemical synthesis of inosine 5'-nucleotides. (2nd June 2020)

• Record Type: Journal Article
• Authors: Senthilvelan, Annamalai; Shanmugasundaram, Muthian; Kore, Anilkumar R.
• Is Part Of: Nucleosides, nucleotides & nucleic acids. Volume 39:Number 6(2020)
• Page Start: 829
• Page End: 837
• Publication Date: 2020-06-02
• Subjects: Regioselective -- inosine -- non-canonical nucleotides -- one-pot synthesis; Nucleosides -- Periodicals; Nucleotides -- Periodicals; Nucleic acids -- Periodicals; 572.8
• DOI: 10.1080/15257770.2019.1708388
• Languages: English
• ISSNs: 1525-7770

Abstract

Abstract: A facile, straightforward, reliable, and efficient chemical synthesis of inosine nucleotides such as inosine-5′-monophosphate, inosine-5′-diphosphate, and inosine-5′-triphosphate, starting from inosine is delineated. The inosine-5′-monophosphate is achieved by the highly regioselective monophosphorylation of inosine using the Yoshikawa procedure. The inosine-5′-diphosphate is obtained by the coupling reaction of tributylammonium phosphate with an activated inosine-5′-monophosphate using zinc chloride as a catalyst. The inosine-5′-triphosphate is efficiently achieved by the improved "one-pot, three-step" Ludwig synthetic strategy. In all the cases, the resulting final product is isolated in good yields with high purity (>99.5%).