Synlett 2017; 28(01): 64-67
DOI: 10.1055/s-0036-1589414
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© Georg Thieme Verlag Stuttgart · New York

Thiophosphate – A Versatile Prebiotic Reagent?

Dougal J. Ritson*, Jiangfeng Xu, John D. Sutherland*
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Publication History

Received: 01 August 2016

Accepted after revision: 11 October 2016

Publication Date:
27 October 2016 (eFirst)

Abstract

Described are our preliminary studies on the reactivity of thiophosphate in a setting which correlates with the cyanosulfidic systems chemistry we have previously reported. Thiophosphate adds to various nitrile groups giving the corresponding thioamides in a highly efficient manner and the mechanistic implications are briefly discussed. Thiophosphate can also act as a phosphorylating agent, which was demonstrated with adenosine. The prebiotic availability of thiophosphate must be questioned, but if a plausible synthesis can be found, the advantages it would bring to the field of prebiotic chemistry appear to be highly beneficial.

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