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

Thiophosphate – A Versatile Prebiotic Reagent?

Dougal J. Ritson*
MRC – Laboratory of Molecular Biology, Francis Crick Avenue, Cambridge Biomedical Campus, Cambridge, CB2 0QH, UK   Email: johns@mrc-lmb.cam.ac.uk   Email: dritson@mrc-lmb.cam.ac.uk
,
Jiangfeng Xu
MRC – Laboratory of Molecular Biology, Francis Crick Avenue, Cambridge Biomedical Campus, Cambridge, CB2 0QH, UK   Email: johns@mrc-lmb.cam.ac.uk   Email: dritson@mrc-lmb.cam.ac.uk
,
John D. Sutherland*
MRC – Laboratory of Molecular Biology, Francis Crick Avenue, Cambridge Biomedical Campus, Cambridge, CB2 0QH, UK   Email: johns@mrc-lmb.cam.ac.uk   Email: dritson@mrc-lmb.cam.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 01 August 2016

Accepted after revision: 11 October 2016

Publication Date:
27 October 2016 (online)


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.

Supporting Information

 
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