Chemical Synthesis of a Locked Nucleic Acid–Substituted Dinucleotide Cap Analog. Issue 1 (20th January 2021)

• Record Type: Journal Article
• Authors: Shanmugasundaram, Muthian; Senthilvelan, Annamalai; Kore, Anilkumar R.
• Is Part Of: Current protocols. Volume 1:Issue 1(2021)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-01-20
• Subjects: 7‐methylguanosine -- anti‐reverse cap analog -- eukaryotic mRNA -- locked nucleic acid -- regioselective; Life sciences -- Laboratory manuals -- Periodicals; Biology -- Laboratory manuals -- Periodicals; Life sciences -- Technique -- Periodicals; Biology -- Technique -- Periodicals; 570.028
• DOI: 10.1002/cpz1.22
• Languages: English
• ISSNs: 2691-1299

Abstract

Abstract: This article describes a reliable and efficient method for synthesis of the dinucleotide cap analog m 7(LNA) G[5′]ppp[5′]G containing a locked nucleic acid moiety. The required LNA intermediate for the final coupling reaction, m 7(LNA) GDP, is prepared in six steps starting from 5′‐DMTr‐ N ‐DMF LNA guanosine. The overall reaction involves removal of DMTr and DMF groups, 5′ monophosphorylation, imidazolide formation, diphosphorylation, and regioselective m 7 methylation. The final coupling reaction of m 7(LNA) GDP with ImGMP in the presence of zinc chloride as a catalyst affords m 7(LNA) G[5′]ppp[5′]G in 59% yield. © 2021 Wiley Periodicals LLC. Basic Protocol : Synthesis of an LNA‐substituted dinucleotide cap analog Support Protocol : Preparation of the tris(tributylammonium) phosphate linker