Straightforward Ball‐Milling Access to Dinucleoside 5′, 5′‐Polyphosphates via Phosphorimidazolide Intermediates. Issue 10 (21st January 2019)

• Record Type: Journal Article
• Authors: Appy, Lucie; Depaix, Anaïs; Bantreil, Xavier; Lamaty, Frédéric; Peyrottes, Suzanne; Roy, Béatrice
• Is Part Of: Chemistry. Volume 25:Issue 10(2019)
• Page Start: 2477
• Page End: 2481
• Publication Date: 2019-01-21
• Subjects: 1, 1′-carbonyldiimidazole -- green chemistry -- mechanochemistry -- nucleotides -- pyrophosphate; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201805924
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A solvent‐assisted mechanochemical approach to access symmetrical and mixed dinucleoside 5, 5′‐polyphosphates is reported. Under ball‐milling conditions, nucleoside 5′‐monophosphates were quantitatively activated using 1, 1′‐carbonyldiimidazole, forming their phosphorimidazolide derivatives. The addition of a nucleoside 5′‐mono‐, di‐ or triphosphate directly led to the formation of the corresponding dinucleotides. Benefits of the reported one‐pot method include the use of unprotected nucleotides in their sodium or acid form, activation by the eco‐friendly 1, 1′‐carbonyldiimidazole, non‐dry conditions, short reaction time, high conversion rates, and easy setup and purification. This work offers new perspectives for the synthesis of nucleotide conjugates and analogues, combining the phosphorimidazolide approach and milling conditions. Abstract : A sustainable, practical, eco‐friendly approach to provide access to symmetrical and mixed dinucleoside 5′, 5′‐polyphosphates is reported. Under ball‐milling conditions, nucleoside 5′‐monophosphates were quantitatively transformed into their phosphorimidazolide derivatives through activation with 1, 1 ′ ‐carbonyldiimidazole. The addition of a nucleoside 5′‐mono‐, di‐, or triphosphate directly led to the formation of the corresponding dinucleotides.