Selective phosphonylation of 5′-adenosine monophosphate (5′-AMP) via pyrophosphite [PPi(III)]

Kaye, K., Bryant, D. E., Marriott, K. E.R., Ohara, S., Fishwick, C. W.G. and Kee, T. P. (2016) Selective phosphonylation of 5′-adenosine monophosphate (5′-AMP) via pyrophosphite [PPi(III)]. Origins of Life and Evolution of Biospheres, 46(4), pp. 425-434. (doi: 10.1007/s11084-016-9497-y) (PMID:27220497) (PMCID:PMC5050244)

[img]
Preview
Text
141565.pdf - Published Version
Available under License Creative Commons Attribution.

1MB

Abstract

We describe here experiments which demonstrate the selective phospho-transfer from a plausibly prebiotic condensed phosphorus (P) salt, pyrophosphite [H2P2O52−; PPi(III)], to the phosphate group of 5′-adenosine mono phosphate (5′-AMP). We show further that this P-transfer process is accelerated both by divalent metal ions (M2+) and by organic co-factors such as acetate (AcO−). In this specific case of P-transfer from PPi(III) to 5′-AMP, we show a synergistic enhancement of transfer in the combined presence of M2+ & AcO−. Isotopic labelling studies demonstrate that hydrolysis of the phosphonylated 5′-AMP, [P(III)P(V)-5′-AMP], proceeds via nuceophilic attack of water at the Pi(III) terminus.

Item Type:Articles
Additional Information:The authors thank the EPSRC (grant EP/F042558/1), the Leverhulme Trust (grant F07112AA) and the UK Space Agency (Aurora Fellowship to TPK, 2009-12) for financial support of this work. This work was also supported by COST Action TD 1308 ORIGINS (life-origins.com).
Keywords:Astrobiology, phosphorus, prebiotic chemistry, origin of life, nucleotides.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Marriott, Miss Katie
Authors: Kaye, K., Bryant, D. E., Marriott, K. E.R., Ohara, S., Fishwick, C. W.G., and Kee, T. P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Origins of Life and Evolution of Biospheres
Publisher:Springer
ISSN:0169-6149
ISSN (Online):1573-0875
Published Online:24 May 2016
Copyright Holders:Copyright © 2016 The Authors
First Published:First published in Origins of Life and Evolution of Biospheres 46(4): 425-434
Publisher Policy:Reproduced under a Creative Commons License

University Staff: Request a correction | Enlighten Editors: Update this record