Cited by 1,711Physical Organic Chemistry and Reaction KineticsOrganophosphorus compounds synthesisOrigins and Evolution of Life

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Why Nature Chose Phosphates

Westheimer, F. H.·1987·Science

DOI 10.1126/science.2434996

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Abstract

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 within 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 negative charges can react by way of the monomeric metaphosphate ion PO 3 - 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.

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Lee, O., Yang, K., Kang, K., et al. (2004) · Journal of Computational Chemistry · doi:10.1002/jcc.20104 · Cited by 10
DNA binding, docking studies, artificial nuclease activity and in vitro cytotoxicity of newly synthesized steroidal 1H–pyrimidines
Shamsuzzaman, Dar, A. M., Tabassum, S., et al. (2013) · Comptes Rendus Chimie · doi:10.1016/j.crci.2013.07.001 · Cited by 10
Synthesis of Various Schiff Bases Containing Isoxazole Ring and Their Applications with Thioglycollic Acid and Diverse Phosphorus Reagents
Shaddy, A. A., Abu‐Bakr, S. M., & Khidre, M. D. (2015) · Journal of Heterocyclic Chemistry · doi:10.1002/jhet.2541 · Cited by 10
Excretion by Benthic Invertebrates as Important Source of Phosphorus in Oligotrophic Ecosystem (Lake Krivoe, Northern Russia)
Александровна, Б. Н., Maximov, A. A., Umnova, L. P., et al. (2017) · Journal of Siberian Federal University Biology · doi:10.17516/1997-1389-0046 · Cited by 10
Use of synchrotron radiation X‐ray fluorescence and X‐ray absorption spectroscopy to investigate bioaccumulation, molecular target, and biotransformation of volcanic elements
Lamela, P. A., Perez, R. D., Perez, C. A., et al. (2018) · X-Ray Spectrometry · doi:10.1002/xrs.2843 · Cited by 10
The Zn(II)-1,4,7-Trimethyl-1,4,7-Triazacyclononane Complex: A Monometallic Catalyst Active in Two Protonation States
Diez‐Castellnou, M., Salassa, G., Mancin, F., et al. (2019) · Frontiers in Chemistry · doi:10.3389/fchem.2019.00469 · Cited by 10
“Still, the hydrolytic processing of nucleic acids occurs in living organism in few milliseconds, thanks to the enzymes devoted to this task, as nucleases and phosphatases (Westheimer, 1987; Kamerlin et al., 2013).”
Background
Specific acclimations to phosphorus limitation in the marine diatom Phaeodactylum tricornutum
Dell’Aquila, G., & Maier, U. G. (2020) · Biological Chemistry · doi:10.1515/hsz-2020-0197 · Cited by 10
A2BBi2(PO4)2(P2O7) (A = K, Rb, B = Pb, Cd): the Effect of Cation Sizes on Structural Evolution
Qi, L., Chen, Z., Li, L., et al. (2020) · European Journal of Inorganic Chemistry · doi:10.1002/ejic.202000716 · Cited by 10
Cellular and mitochondrial calcium communication in obstructive lung disorders
Sagar, S., Kapoor, H., Chaudhary, N., & Roy, S. S. (2021) · Mitochondrion · doi:10.1016/j.mito.2021.03.005 · Cited by 12
The phosphorus cycle and biological pump in Earth’s middle age: Reappraisal of the “Boring Billion”
Huang, T., Wang, R., & Shen, B. (2022) · Chinese Science Bulletin (Chinese Version) · doi:10.1360/tb-2021-1168 · Cited by 10
A Phosphoramidite Analogue of Cyclotriphosphate Enables Iterative Polyphosphorylations
Singh, J., Steck, N., De, D., et al. (2019) · Angewandte Chemie · doi:10.1002/ange.201814366 · Cited by 10
Arsenic. Can This Toxic Metalloid Sustain Life?
Wilcox, D. E. (2013) · Metal ions in life sciences · doi:10.1007/978-94-007-7500-8_15 · Cited by 10
Gas-phase reactions of sulfides, mercaptans, and dimethyl methylphosphonate with ionic species derived from argon and water
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Hydration of biological molecules: Lipids versus nucleic acids
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Mechanistic Investigation into the Cleavage of a Phosphomonoester Mediated by a Symmetrical Oxyimine‐Based Macrocyclic Zinc(II) Complex
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Synthesis and characterization of novel phosphoramidates containing benzimidazole moiety
Yılmaz, Ü., & Küçükbay, H. (2015) · Phosphorus, sulfur, and silicon and the related elements · doi:10.1080/10426507.2015.1067209 · Cited by 10
Phosphoryl group differentiating α‐amino acids from β‐ and γ‐amino acids in prebiotic peptide formation
Jiang, Y., Tan, B., Chen, Z., et al. (2003) · International Journal of Quantum Chemistry · doi:10.1002/qua.10562 · Cited by 10
Chemistry and Enzymology of Phosphatases
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Efficiency of phosphorus resource use in Africa as defined by soil chemistry and the impact on crop production
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“At the simplest conceptual level two pools can be considered [1–3]: firstly a labile pool from which plants can uptake P [8,9], and secondly a stable pool which is unavailable to the plants [10].”
Ag(I)-catalyzed cyclization reaction of ethyl o-hydroxyphenylethynylphosphinates to phosphachromones
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Artificial Hydrolytic Metalloenzymes
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Search for the Most Primitive Membranes: Some Remaining Problems
Nakatani, Y., Ribeiro, N., Streiff, S., Désaubry, L., & Ourisson, G. (2012) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-012-9313-2 · Cited by 11
“The indispensable role of phosphates in many aspects of biochemistry is attributed to the specific properties of this group (Westheimer 1987).”
Background

Authors: Westheimer, F. H.
Affiliations: Harvard University (US)
Corresponding author: Westheimer, F. H.
Venue: Science
Publisher: American Association for the Advancement of Science (AAAS)
Published: 1987-03-06
Volume: 235
Issue: 4793
Pages: 1173-1178
ISSN: 0036-8075 (ISSN-L)
1095-9203
DOI: 10.1126/science.2434996
OpenAlex: W2064761203
Semantic Scholar: 5ca074c6259fad7d448fb8587c394e507dd3ee19
Cited by: 1,711
References: 60
Citations by year: 2026: 68 · 2025: 75 · 2024: 96 · 2023: 89 · 2022: 90 · 2021: 80 · 2020: 77 · 2019: 71 · 2018: 68 · 2017: 71 · 2016: 54 · 2015: 84 · 2014: 69 · 2013: 62 · 2012: 65
FWCI: 14.06
Type: journal article
Language: en
Open access: closed
Locations: Science (publishedVersion)
PubMed (publishedVersion)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Physical Organic Chemistry and Reaction Kinetics
Physical Sciences › Chemistry › Organic Chemistry › Organophosphorus compounds synthesis
Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
Keywords: phosphate, phosphoric acid, nucleic acids, energy storage, enzyme catalysis
MeSH terms: Amides, Animals, Arsenates, Chemistry, Citrates, Electrochemistry, Humans, Hydrolysis, Ions, Nucleic Acids, Phosphates, RNA, Silicic Acid, Citric Acid, Chemical Phenomena

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