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A Simple Complex on the Verge of Breakdown: Isolation of the Elusive Cyanoformate Ion

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Murphy, L. J., Robertson, K. N., Harroun, S. G., Brosseau, C. L., Werner-Zwanziger, U., Moilanen, J., Tuononen, H., & Clyburne, J. A. C. (2014). A Simple Complex on the Verge of Breakdown: Isolation of the Elusive Cyanoformate Ion. Science, 344(6179), 75-78. https://doi.org/10.1126/science.1250808
Published in
Science
Authors
Murphy, Luke J. |
Robertson, Katherine N. |
Harroun, Scott G. |
Brosseau, Christa L. |
Werner-Zwanziger, Ulrike |
Moilanen, Jani |
Tuononen, Heikki |
Clyburne, Jason A. C.
Date
2014
Discipline
Epäorgaaninen ja analyyttinen kemiaInorganic and Analytical Chemistry
Copyright
© 2014 American Association for the Advancement of Science. This is a final draft version of an article whose final and definitive form has been published by AAAS. Published in this repository with the kind permission of the publisher.

 
Why does cyanide not react destructively with the proximal iron center at the active site of 1-aminocyclopropane-1-carboxylic acid (ACC) oxidase, an enzyme central to the biosynthesis of ethylene in plants? It has long been postulated that the cyanoformate anion, [NCCO2]–, forms and then decomposes to carbon dioxide and cyanide during this process. We have now isolated and crystallographically characterized this elusive anion as its tetraphenylphosphonium salt. Theoretical calculations show that cyanoformate has a very weak C–C bond and that it is thermodynamically stable only in low dielectric media. Solution stability studies have substantiated the latter result. We propose that cyanoformate shuttles the potentially toxic cyanide away from the low dielectric active site of ACC oxidase before breaking down in the higher dielectric medium of the cell.
Publisher
American Association for the Advancement of Science
ISSN Search the Publication Forum
0036-8075
Keywords
syanoformaatti kiderakenne kemiallinen sitoutuminen cyanofrmate crystal structure chemical bonding
DOI
https://doi.org/10.1126/science.1250808
URI

http://urn.fi/URN:NBN:fi:jyu-201511263834

Publication in research information system

https://converis.jyu.fi/converis/portal/detail/Publication/23790869

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