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Science-P - DOI 10.1126/science.2434996 1173(1987 235...

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Unformatted text preview: DOI: 10.1126/science.2434996 , 1173 (1987); 235 Science et al. FH Westheimer, Why nature chose phosphates www.sciencemag.org (this information is current as of January 8, 2007 ): The following resources related to this article are available online at http://www.sciencemag.org version of this article at: including high-resolution figures, can be found in the online Updated information and services, http://www.sciencemag.org#otherarticles , 7 of which can be accessed for free: cites 29 articles This article http://www.sciencemag.org#otherarticles 15 articles hosted by HighWire Press; see: cited by This article has been http://www.sciencemag.org/help/about/permissions.dtl in whole or in part can be found at: this article permission to reproduce of this article or about obtaining reprints Information about obtaining registered trademark of AAAS. c 2006 by the American Association for the Advancement of Science; all rights reserved. The title SCIENCE is a Copyright American Association for the Advancement of Science, 1200 New York Avenue NW, Washington, DC 20005. Science (print ISSN 0036-8075; online ISSN 1095-9203) is published weekly, except the last week in December, by the on January 8, 2007 www.sciencemag.org Downloaded from Why Nature Chose Phosphates F. H. WESTHEIMER Phosphate esters and anhydrides dominate the living world but are seldom used as intermediates by organic chemists. Phosphoric acid is specially adapted for its role in nucleic acids because it can link two nucleotides and still ionize; the resulting negative charge serves both to stabilize the diesters against hydrolysis and to retain the molecules witin a lipid membrane. A similar explanation for stability and retention also holds for phosphates that are intermediary metabolites and for phosphates that serve as energy sources. Phosphates with multiple nega- tive charges can react by way ofthe monomeric metaphos- phate ion P03 as an intermediate. No other residue appears to fulfill the multiple roles of phosphate .in biochemistry. Stable, negatively charged phosphates. react under catalysis by enzymes; organic chemists, who can only rarely use enzymatic catalysis for their reactions, need more highly reactive intermediates than phosphates. P HOSPHATE ESTERSANDANHYDRIDES DOMINATETHE LIV- ing world. The genetic materials DNA and RNA are phos- phodiesters. Most of the coenzymes are esters of phosphoric or pyrophosphoric acid. The principal reservoirs of biochemical energy [adenosine triphosphate (ATP), creatine phosphate; and phosphoenolpyruvate] are phosphates. Many intermediary metabo- lites are phosphate esters, and phosphates or pyrophosphates are essential intermediates in biochemical syntheses and degradations....
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Science-P - DOI 10.1126/science.2434996 1173(1987 235...

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