Dehydration promotes phosphoramidate-linked amino acidyl and peptido adenosine conjugates

Cyclic nucleoside phosphates have been shown previously to be adequately activated to oligomerise under dry conditions. Herein, it is demonstrated that 3′,5′-cyclic adenosine monophosphate (3′,5′-cAMP) and glycine when subjected to dehydration under alkaline conditions form phosphoramidate-linked co...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-10, Vol.6 (83), p.1192-11923
Main Authors: Deckel, Yaam, Brown, Joshua J, Senthilkumar, Tejaswi, Fahrenbach, Albert C
Format: Article
Language:English
Subjects:
Adenosine monophosphate
Conjugates
Dehydration
Glycine
Phosphates
Reaction mechanisms
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Summary:Cyclic nucleoside phosphates have been shown previously to be adequately activated to oligomerise under dry conditions. Herein, it is demonstrated that 3′,5′-cyclic adenosine monophosphate (3′,5′-cAMP) and glycine when subjected to dehydration under alkaline conditions form phosphoramidate-linked conjugates. Solid-state reaction mechanisms investigated by DFT suggest why the reaction does not occur efficiently in the aqueous phase. 3′,5′-Cyclic adenosine monophosphate (3′,5′-cAMP) and glycine subjected to alkaline dehydration yield phosphoramidate-linked conjugates.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc03602f