Synlett 2017; 28(01): 78-83
DOI: 10.1055/s-0036-1588626
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© Georg Thieme Verlag Stuttgart · New York

Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water

Christian Fernández-García, Matthew W. Powner*
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Publication History

Received: 03 August 2016

Accepted after revision: 20 September 2016

Publication Date:
11 October 2016 (eFirst)

Abstract

A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.

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