One‐Pot Synthesis of Nucleotides and Conjugates in Aqueous Medium. Issue 2 (14th December 2016)

• Record Type: Journal Article
• Authors: Depaix, Anaïs; Peyrottes, Suzanne; Roy, Béatrice
• Is Part Of: European journal of organic chemistry. Issue 2(2017)
• Page Start: 241
• Page End: 245
• Publication Date: 2016-12-14
• Subjects: Nucleosides -- Nucleotides -- Phosphorylation -- Synthetic methods -- Water chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601299
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Herein, we describe a one‐pot synthesis, in a mixture of water/acetonitrile, of nucleoside 5′‐polyphosphates and some derivatives starting from their corresponding nucleoside 5′‐monophosphates. Phosphorimidazolide intermediates are formed in the presence of imidazole and 2‐chloro‐1, 3‐dimethylimidazolinium hexafluorophosphate. Under these mild conditions, nucleoside 5′‐di‐ and 5′‐triphosphates, dinucleoside 5′, 5′‐polyphosphates, as well as some nucleotide analogues modified either on the nucleoside or on the phosphate moieties are obtained in moderate to high yields. Abstract : A two‐step reaction sequence for the preparation of nucleoside 5′‐polyphosphates in a mixture of water/acetonitrile is developed. This method also provides access to nucleotide analogues, modified either on the nucleoside or on the phosphate moieties. NDP = nucleoside 5′‐diphosphate, NTP = nucleoside 5′‐triphosphate, DNP = dinucleoside 5′, 5′‐polyphosphate, CDP = cytidine 5′‐diphosphate.