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

The DOI matches its Crossref record; 60 of the 60 references it cites were found in a registry or an index.

Why Nature Chose Phosphates

Westheimer, F. H.·1987·Science

DOI 10.1126/science.2434996

Open this paper in CoChat — free account

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.

Integrity signals

Registry

Crossref · 10.1126/science.2434996

Cites

60 of 60 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

The RNA moiety of ribonuclease P is the catalytic subunit of the enzyme
Guerrier-Takada, C., Gardiner, K., Marsh, T., Pace, N., & Altman, S. (1983) · Cell · doi:10.1016/0092-8674(83)90117-4 · Cited by 2,684
Reduction of Ribonucleotides
Thelander, L., & Reichard, P. A. (1979) · Annual Review of Biochemistry · doi:10.1146/annurev.bi.48.070179.001025 · Cited by 1,160
Enzyme-Catalyzed Phosphoryl Transfer Reactions
Knowles, J. R. (1980) · Annual Review of Biochemistry · doi:10.1146/annurev.bi.49.070180.004305 · Cited by 1,145
Evolution of the genetic apparatus
Orgel, L. E. (1968) · Journal of Molecular Biology · doi:10.1016/0022-2836(68)90393-8 · Cited by 996
Pseudo-rotation in the hydrolysis of phosphate esters
Westheimer, F. H. (1968) · Accounts of Chemical Research · doi:10.1021/ar50003a002 · Cited by 772
Self-citation
Effective Molarities for Intramolecular Reactions
Kirby, A. J. (1980) · Advances in physical organic chemistry · doi:10.1016/s0065-3160(08)60129-x · Cited by 579
The Intervening Sequence RNA of Tetrahymena Is an Enzyme
Zaug, A. J., & Cech, T. R. (1986) · Science · doi:10.1126/science.3941911 · Cited by 507
Coenzymes as fossils of an earlier metabolic state
White, H. B. (1976) · Journal of Molecular Evolution · doi:10.1007/bf01732468 · Cited by 493
24 Bovine Pancreatic Ribonuclease
Richards, F. M., & Wyckoff, H. W. (1971) · The Enzymes · doi:10.1016/s1874-6047(08)60384-4 · Cited by 441
The Electrostatic Influence of Substituents on the Dissociation Constants of Organic Acids. I
Kirkwood, J. G., & Westheimer, F. H. (1938) · The Journal of Chemical Physics · doi:10.1063/1.1750302 · Cited by 414
Self-citation

Flagged first, then by citations

Show all 60 references

Research works printed but not linked: 14

BAILLY, M.C., BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE 9: 314 (1942).
BARBY, D, SPEC PUBL CHEM SOC 31: 320 (1977).
BARNARD, PWC, THE HYDROLYSIS OF ORGANIC PHOSPHATES, CHEMISTRY & INDUSTRY: 760 (1955).
BELSKII, V.E., B ACAD SCI USSR: 2427 (1967).
BJERRUM, N, Dissociation constants of very basic acids and use of this for the evaluation of molecular dimensions., ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE--STOCHIOMETRIE UND VERWANDTSCHAFTSLEHRE 106: 219 (1923).
BLOCH, K, CIBA FDN S BIOS TERP: 4 (1959).
CRAFTS, J.M., BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE 14: 99 (1870).
EBELMAN, JUSTUS LIEBIGS ANNALEN DER CHEMIE 57: 334 (1846).
KIRBY, A.J., ADVANCES IN PHYSICAL ORGANIC CHEMISTRY 17: 183 (1980).
KIRBY, A.J., COMPREHENSIVE CHEM K 10: 153 (1972).
LIPPMANN, F, PHOSPHORUS METABOLIS 1: 521 (1951).
PINNOW, J, ZEITSCHRIFT FUR ELEKTROCHEMIE 24: 21 (1918).
POULTER, C.D., BIOSYNTHESIS ISOPREN 1: 161 (1981).
STRYER, L, BIOCHEMISTRY: 499 (1981).

Sorted by citations

Items 601–700 of 1,000

At the Intersection of Chemistry, Biology, and Medicine
Walsh, C. T. (2017) · Annual Review of Biochemistry · doi:10.1146/annurev-biochem-110716-121241 · Cited by 25
Oligonucleotide analogues with cationic backbone linkages
Meng, M., & Ducho, C. (2018) · Beilstein Journal of Organic Chemistry · doi:10.3762/bjoc.14.111 · Cited by 25
Prebiotic Pathway from Ribose to RNA Formation
Bánfalvi, G. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22083857 · Cited by 26
“Phosphate is specifically adapted for its role to protect nucleic acids because by connecting two ribose diesters against hydrolysis and still ionizes resulting in negative charge and stabilizes phosphomonoesters even more [58].”
Background
Prodrugs of pyrophosphates and bisphosphonates: disguising phosphorus oxyanions
Rudge, E. S., Chan, A. H. Y., & Leeper, F. J. (2022) · RSC Medicinal Chemistry · doi:10.1039/d1md00297j · Cited by 26
Spiro- and substituted tetrahydrobenzo[b]thiophene-triazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies
Abdou, W. M., Ganoub, N. A., & Sabry, E. (2015) · Monatshefte für Chemie - Chemical Monthly · doi:10.1007/s00706-015-1542-4 · Cited by 25
Synthesis and biological studies of steroidal pyran based derivatives
SHAMSUZZAMAN, Dar, A. M., Khan, Y., et al. (2013) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2013.09.004 · Cited by 25
Crystal structure of the phosphate-binding protein (PBP-1) of an ABC-type phosphate transporter from Clostridium perfringens
Gonzalez, D., Richez, M., Bergonzi, C., et al. (2014) · Scientific Reports · doi:10.1038/srep06636 · Cited by 25
“The gene was cloned into a pET22b (1) plasmid, using NcoI and NotI as cloning sites.”
BackgroundMethod
Divalent and Multivalent Activation in Phosphate Triesters: A Versatile Method for the Synthesis of Advanced Polyol Synthons
Thomas, C. D., McParland, J. P., & Hanson, P. R. (2009) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200900560 · Cited by 25
The Role of Biota in Shaping the Phosphorus Cycle in Lakes
Istvánovics, V. (2008) · Freshwater Reviews · doi:10.1608/frj-1.2.2 · Cited by 25
“Simultaneously, the charged phosphoesters can be retained within the lipid membrane (Westheimer, 1987).”
Background
Did Cyclic Metaphosphates Have a Role in the Origin of Life?
Glonek, T. (2021) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-021-09604-5 · Cited by 27
“2004; Kulaev and Vagabov 1983; Lazcano and Miller 1996; Locker 1973; Oró 1994; Westheimer 1987 Archaen, Eoarchaen Karki et al.”
Background
Esterification of Carboxylic Acids with (β-Diazo-α,α-difluoroethyl)phosphonates under Photochemical Conditions
Liu, J., Xu, J., Pajkert, R., et al. (2021) · 化学学报 · doi:10.6023/a21030096 · Cited by 25
Search for the Most ‘primitive’ Membranes and Their Reinforcers: A Review of the Polyprenyl Phosphates Theory
Nakatani, Y., Ribeiro, N., Streiff, S., Gotoh, M., Pozzi, G., Désaubry, L., & Milon, A. (2014) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-014-9365-6 · Cited by 27
Growth of Organic Microspherules in Sugar-Ammonia Reactions
Weber, A. L. (2005) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-005-0234-1 · Cited by 25
Ab Initio Study of the Thiolysis of Trimethyl Phosphate Ester in the Gas Phase
Menegon, G., Loos, M., & Chaimovich, H. (2002) · The Journal of Physical Chemistry A · doi:10.1021/jp026083i · Cited by 25
Intermolecular Phosphoryl Transfer of N‐Phosphoryl Amino Acids
Gao, X., Deng, H., Tang, G., Liu, Y., Xu, P., & Zhao, Y. (2011) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201100234 · Cited by 27
Comment on “A Bacterium That Can Grow by Using Arsenic Instead of Phosphorus”
Borhani, D. W. (2011) · Science · doi:10.1126/science.1201255 · Cited by 25
On the aqueous origins of the condensation polymers of life
Whitaker, D. E., & Powner, M. W. (2024) · Nature Reviews Chemistry · doi:10.1038/s41570-024-00648-5 · Cited by 27
“ATP is thermodynamically unstable towards hydrolysis in water, but it is kinetically stable 25,26 .”
A Path toward SARS-CoV-2 Attenuation: Metabolic Pressure on CTP Synthesis Rules the Virus Evolution
Ou, Z., Ouzounis, C., Wang, D., Sun, W., Li, J., Chen, W., Marlière, P., & Danchin, A. (2020) · Genome Biology and Evolution · doi:10.1093/gbe/evaa229 · Cited by 24
Stable Isotope Phosphate Labelling of Diverse Metabolites is Enabled by a Family of 18 O‐Phosphoramidites**
Haas, T., Mundinger, S., Qiu, D., et al. (2021) · Angewandte Chemie International Edition · doi:10.1002/anie.202112457 · Cited by 24
RNA-inspired intramolecular transesterification accelerates the hydrolysis of polyethylene-like polyphosphoesters
Haider, T. P., Suraeva, O., Lieberwirth, I., Paneth, P., & Wurm, F. R. (2021) · Chemical Science · doi:10.1039/d1sc05509g · Cited by 24
EUTROPHICATION AND PREDATION RISK INTERACT TO AFFECT SEXUAL TRAIT EXPRESSION AND MATING SUCCESS
Cothran, R. D., Stiff, A. R., Jeyasingh, P. D., & Relyea, R. A. (2011) · Evolution · doi:10.1111/j.1558-5646.2011.01475.x · Cited by 26
Synthesis and biological evaluation of copper( ii ) pyrenethiosemicarbazone
Ingle, S. A., Kate, A. N., Kumbhar, A. A., et al. (2015) · RSC Advances · doi:10.1039/c5ra00020c · Cited by 24
Straightforward approach to efficient oxidative DNA cleaving agents based on Cu(ii) complexes of heterosubstituted cyclens
Hormann, J., Perera-Bobusch, C., Deibel, N., Lentz, D., Sarkar, B., & Kulak, N. (2013) · Dalton Transactions · doi:10.1039/c3dt32857k · Cited by 25
In vitro and in vivo degradation studies of a novel linear copolymer of lactide and ethylphosphate
Chaubal, M. V., Su, G., Spicer, E., Dang, W., Branham, K. E., English, J. P., & Zhao, Z. (2003) · Journal of Biomaterials Science Polymer Edition · doi:10.1163/15685620360511137 · Cited by 24
Deciphering the Mechanism of RNase T1
Loverix, S., & Steyaert, J. (2001) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/s0076-6879(01)41160-8 · Cited by 24
Phosphorylated aminosugars; synthesis, properties, and reactivity in enzymic reactions
Sem, D. S., & Cleland, W. W. (1991) · Biochemistry · doi:10.1021/bi00234a020 · Cited by 24
Metallomicellar catalysis: accelerated hydrolysis of BNPP by copper(II), zinc(II), and nickel(II) complexes of long alkanol–imidazole in CTAB micellar solution
Fubin, J., Du, J., Xiaoqi, Y., et al. (2004) · Journal of Colloid and Interface Science · doi:10.1016/j.jcis.2004.01.078 · Cited by 24
Catalytic Hydrolysis of Adenosine 2‘,3‘-Cyclic Monophosphate by CuII Terpyridine
Jenkins, L. A., Bashkin, J. K., Pennock, J. D., et al. (1999) · Inorganic Chemistry · doi:10.1021/ic990228r · Cited by 24
Double-strand hydrolysis of DNA by a magnesium(II) complex with diethylenetriamine
Yang, P., Ren, R., Guo, M., Song, A., Meng, X., Yuan, C., Zhou, Q., Chen, H., Xiong, Z., & Gao, X. (2004) · JBIC Journal of Biological Inorganic Chemistry · doi:10.1007/s00775-004-0548-x · Cited by 24
Antibody‐Catalyzed Phosphate Triester Hydrolysis
Rosenblum, J. S., Lo, L., Li, T., et al. (1995) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199522751 · Cited by 24
ATP Synthases in the Year 2000: Defining the Different Levels of Mechanism and Getting a Grip on Each
Pedersen, P. L., Ko, Y. H., & Hong, S. (2000) · Journal of Bioenergetics and Biomembranes · doi:10.1023/a:1005652605340 · Cited by 24
Iterative Synthese von Nukleosidoligophosphaten mit Phosphoramiditen
Cremosnik, G. S., Hofer, A., & Jessen, H. J. (2013) · Angewandte Chemie · doi:10.1002/ange.201306265 · Cited by 23
Prebiotically Plausible “Patching” of RNA Backbone Cleavage through a 3′–5′ Pyrophosphate Linkage
Wright, T. H., Giurgiu, C., Zhang, W., Radakovic, A., O’Flaherty, D. K., Zhou, L., & Szostak, J. W. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.9b08237 · Cited by 23
Balanced Polarizable Drude Force Field Parameters for Molecular Anions: Phosphates, Sulfates, Sulfamates and Oxides
Kognole, A., Aytenfisu, A. H., & MacKerell, A. D. J. (2020) · Journal of Molecular Modeling · doi:10.1007/s00894-020-04399-0 · Cited by 21
The McKenna reaction – avoiding side reactions in phosphonate deprotection
Justyna, K., Małolepsza, J., Kusy, D., Maniukiewicz, W., & Błażewska, K. M. (2020) · Beilstein Journal of Organic Chemistry · doi:10.3762/bjoc.16.119 · Cited by 25
Effect of Environmental Stress on the Nutrient Stoichiometry of the Clonal Plant Phragmites australis in Inland Riparian Wetlands of Northwest China
Zhou, Y., Jiao, L., Qin, H., & Li, F. (2021) · Frontiers in Plant Science · doi:10.3389/fpls.2021.705319 · Cited by 24
“This finding conforms to the growth restriction hypothesis, which states that the plant growth rate is adjusted to adapt to changes in the external environment by adjusting the stoichiometric ratio of elements during plant growth, and development (Wu et al., 2021).”
Result
Understanding the complete bioluminescence cycle from a multiscale computational perspective: A review
Liu, Y. (2022) · Journal of Photochemistry and Photobiology C Photochemistry Reviews · doi:10.1016/j.jphotochemrev.2022.100537 · Cited by 23
Synthesis and reactivity of a C3-symmetric trinuclear zinc(ii) hydroxide catalyst efficient at phosphate diester transesterification
Mitra, R., Peters, M. W., & Scott, M. J. (2007) · Dalton Transactions · doi:10.1039/b706386e · Cited by 23
Mixed‐Ligand Copper(II)–Phenanthroline–Dipeptide Complexes: Synthesis, Characterization, and DNA‐Cleavage Properties
Reddy, P. R., & Manjula, P. (2007) · Chemistry & Biodiversity · doi:10.1002/cbdv.200790039 · Cited by 24
Diastereoselective Synthesis of Glycosyl Phosphates by Using a Phosphorylase–Phosphatase Combination Catalyst
Wildberger, P., Pfeiffer, M., Brecker, L., et al. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201507710 · Cited by 23
Synthesis of Dihydrophosphaisocoumarins through a Palladium‐Catalyzed Oxidative Cyclization of Arylphosphonic Acid Monoethyl Esters with 1,3‐Dienes
Son, J., Kim, H., Jeon, W. H., et al. (2017) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201700742 · Cited by 23
Pd(0)-Catalyzed Cyclizative Phosphorylation of (Z)-1-Iodo-1,6-diene: Synthesis of Alkylphosphonate and Alkylthionophosphonate
Hong, Y., Liu, W., Dong, M., et al. (2019) · Organic Letters · doi:10.1021/acs.orglett.9b02149 · Cited by 23
Controlling O2 Reactivity in Synthetic Analogues of [NiFeS]- and [NiFeSe]-Hydrogenase Active Sites
Yang, X., Elrod, L. C., Le, T., et al. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.9b07448 · Cited by 23
Synthesis of new steroidal imidazo [1,2-a] pyridines: DNA binding studies, cleavage activity and in vitro cytotoxicity
Dar, A. M., Shamsuzzaman, & Gatoo, M. A. (2015) · Steroids · doi:10.1016/j.steroids.2015.09.010 · Cited by 23
“Under the uncatalyzed physiological conditions, the phosphodiester bonds of DNA are extremely stable and the half life of DNA for hydrolysis is estimated to be around 200 million years [19].”
Infrared Spectrum of Phosphoenol Pyruvate: Computational and Experimental Studies
Rudbeck, M. E., Kumar, S., Mroginski, M. A., Lill, S. O. N., Blomberg, M. R. A., & Barth, A. (2009) · The Journal of Physical Chemistry A · doi:10.1021/jp809638u · Cited by 23
Tetranuclear Copper(II) Complex with Glucose-1-phosphate and Its Phosphate Ester Exchange with ATP
Kato, M., & Tanase, T. (2004) · Inorganic Chemistry · doi:10.1021/ic0487631 · Cited by 23
High-performance liquid chromatographic determination of pyrophosphate in the presence of a 20,000-fold excess of orthophosphate
Yoza, N., Akazaki, I., Nakazato, T., et al. (1991) · Analytical Biochemistry · doi:10.1016/0003-2697(91)90102-y · Cited by 23
Supramolecular Chemistry, 62. Ligand and Cosubstrate Effects on the Hydrolysis of Phosphate Esters and DNA with Lanthanoids
Rammo, J., & Schneider, H. (1996) · Liebigs Annalen · doi:10.1002/jlac.199619961109 · Cited by 23
Observation of slow dynamic exchange processes in RAS protein crystals by 31P solid state NMR spectroscopy
Stumber, M., Geyer, M., Graf, R., Robert Kalbitzer, H., Scheffzek, K., & Haeberlen, U. (2002) · Journal of Molecular Biology · doi:10.1016/s0022-2836(02)01010-0 · Cited by 22
A greener protocol for the synthesis of phosphorochalcogenoates: Antioxidant and free radical scavenging activities
Mailahn, D. H., Iarocz, L. E. B., Nobre, P. C., et al. (2020) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2020.113052 · Cited by 22
Ab Initio Molecular Dynamics Simulation of the Phosphate Ion in Water: Insights into Solvation Shell Structure, Dynamics, and Kosmotropic Activity
Sharma, B., & Chandra, A. (2017) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.7b06091 · Cited by 22
Selective detection of phospholipids in human blood plasma and single cells for cancer differentiation using dispersed solid-phase microextraction combined with extractive electrospray ionization mass spectrometry
Zhang, H., Lu, H., Huang, K., Li, J., Wei, F., Liú, À., Chingin, K., & Chen, H. (2020) · The Analyst · doi:10.1039/d0an01204a · Cited by 22
Darwin's Warm Little Pond: A One‐Pot Reaction for Prebiotic Phosphorylation and the Mobilization of Phosphate from Minerals in a Urea‐Based Solvent
Burcar, B. T., Pasek, M. A., Gull, M., Cafferty, B. J., Velasco, F., Hud, N. V., & Menor-Salván, C. A. (2016) · Angewandte Chemie · doi:10.1002/ange.201606239 · Cited by 22
Quantum Chemical Modeling of the Cardiolipin Headgroup
Dahlberg, M., Marini, A., Mennucci, B., & Maliniak, A. (2010) · The Journal of Physical Chemistry A · doi:10.1021/jp9110019 · Cited by 21
Supramolecular catalytic systems based on dimeric pyrimidinic surfactants and polyethyleneimine
Zakharov, L. Y., Semenov, V. E., Voronin, M. A., et al. (2008) · Mendeleev Communications · doi:10.1016/j.mencom.2008.05.016 · Cited by 22
Selective site controlled nucleophilic attacks in 5-membered ring phosphate esters: unusual C–O vs. common P–O bond cleavage
Ashkenazi, N., Zade, S. S., Segall, Y., et al. (2005) · Chemical Communications · doi:10.1039/b512117e · Cited by 22
11 Metal Ion Binding and Function in Natural and Artificial Small RNA Enzymes from a Structural Perspective
Wedekind, J. E. (2011) · Royal Society of Chemistry eBooks · doi:10.1039/9781849732512-00299 · Cited by 22
Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels
Pol, M. D., Dai, K., Thomann, R., et al. (2024) · Angewandte Chemie International Edition · doi:10.1002/anie.202404360 · Cited by 21
Multiphosphorylated peptides: importance, synthetic strategies, and applications for studying biological mechanisms.
Samarasimhareddy, M., Mayer, G., Hurevich, M., & Friedler, A. (2020) · Organic and biomolecular chemistry · doi:10.1039/d0ob00499e · Cited by 10
Biomolecular Painstaking Utilization and Assimilation of Phosphorus Under Indigent Stage in Agricultural Crops
Ahmed, S., Choudhury, A. R., Roy, S. K., et al. (2021) · Springer eBooks · doi:10.1007/978-981-16-1350-0_26 · Cited by 21
Common Mechanism of Activated Catalysis in P-loop Fold Nucleoside Triphosphatases—United in Diversity
Kozlova, M. I., Shalaeva, D. N., Dibrova, D. V., & Mulkidjanian, A. Y. (2022) · Biomolecules · doi:10.3390/biom12101345 · Cited by 29
Phosphate availability and implications for life on ocean worlds
Randolph‐Flagg, N. G., Ely, T., Som, S. M., Shock, E. L., German, C. R., & Hoehler, T. M. (2023) · Nature Communications · doi:10.1038/s41467-023-37770-9 · Cited by 26
“It is theorized that phosphate may be required for information-carrying molecules in any form of life 17 due to its ability to form multiple bonds while retaining charge 18 .”
Phosphates as Assisting Groups in Glycan Synthesis
Sletten, E. T., Fittolani, G., Hribernik, N., et al. (2023) · ACS Central Science · doi:10.1021/acscentsci.3c00896 · Cited by 21
Genetically enabling phosphorus fluoride exchange click chemistry in proteins
Cao, L., Yu, B., Li, S., Zhang, P., Li, Q., & Wang, L. (2024) · Chem · doi:10.1016/j.chempr.2024.02.010 · Cited by 21
Phosphogenesis in the 2460 and 2728 million‐year‐old banded iron formations as evidence for biological cycling of phosphate in the early biosphere
Li, Y., Sun, S., & Chan, L. S. (2012) · Ecology and Evolution · doi:10.1002/ece3.443 · Cited by 21
“Phosphorus is a vital nutrient element for the whole living world for making genetic materials, most of coenzymes and biochemical energy carriers (Westheimer 1987).”
Background
Comparison of Cu(II)-Promoted Leaving Group Stabilization of the Cleavage of a Homologous Set of Phosphate Mono-, Di-, and Triesters in Water, Methanol, and Ethanol
Raycroft, M. A. R., Liu, C. T., & Brown, R. S. (2012) · Inorganic Chemistry · doi:10.1021/ic300059e · Cited by 21
The effect of magnesium ions on triphosphate hydrolysis
Barrozo, A. H., Blaha-Nelson, D., Williams, N. H., & Kamerlin, S. C. L. (2017) · Pure and Applied Chemistry · doi:10.1515/pac-2016-1125 · Cited by 21
From chemical metabolism to life: the origin of the genetic coding process
Danchin, A. (2017) · Beilstein Journal of Organic Chemistry · doi:10.3762/bjoc.13.111 · Cited by 21
Aqueous solutions of NMA, Na2HPO4, and NaH2PO4 as models for interaction studies in phosphate–protein systems
Biernacki, K. A., Kaczkowska, E., & Bruździak, P. (2018) · Journal of Molecular Liquids · doi:10.1016/j.molliq.2018.05.104 · Cited by 21
The oxygen isotope composition of bioavailable phosphate in soil reflects the oxygen isotope composition in soil water driven by plant diversity effects on evaporation
Hacker, N., Wilcke, W., & Oelmann, Y. (2019) · Geochimica et Cosmochimica Acta · doi:10.1016/j.gca.2018.11.023 · Cited by 24
Origin of alkylphosphonic acids in the interstellar medium
Turner, A., Abplanalp, M., Bergantini, A., Frigge, R., Zhu, C., Sun, B.-J., Hsiao, C.-T., Chang, A., Meinert, C., & Kaiser, R. (2019) · Science Advances · doi:10.1126/sciadv.aaw4307 · Cited by 19
Sequence isomerism in uniform polyphosphoesters programmes self-assembly and folding
Appukutti, N., Jones, J. R., & Serpell, C. J. (2020) · Chemical Communications · doi:10.1039/d0cc01319f · Cited by 21
Efficient and Convenient One‐Pot Synthesis of Phosphoramidates and Phosphates
Gupta, A. K., Acharya, J., Dubey, D. K., et al. (2007) · Synthetic Communications · doi:10.1080/00397910701483662 · Cited by 21
Electronic Structure of Third-Row Elements in Different Local Symmetries Studied by Valence-to-Core X-ray Emission Spectroscopy
Petrič, M., Bohinc, R., Bučar, K., Nowak, S., Žitnik, M., & Kavčič, M. (2016) · Inorganic Chemistry · doi:10.1021/acs.inorgchem.6b00237 · Cited by 20
Brown Dwarf Atmospheres as the Potentially Most Detectable and Abundant Sites for Life
Lingam, M., & Loeb, A. (2019) · The Astrophysical Journal · doi:10.3847/1538-4357/ab3f35 · Cited by 23
“The last major bioessential element that needs to be addressed is phosphorus (Westheimer 1987).”
Background
Synthesis of 1,2-dihydroisoquinolin-1-ylphosphonates via three-component reactions of 2-(2-formylphenyl)ethanone, amine, and diethyl phosphite
Ye, S., Zhou, H., & Wu, J. (2008) · Tetrahedron · doi:10.1016/j.tet.2008.12.038 · Cited by 21
Archaeal phosphoproteins. Identification of a hexosephosphate mutase and the α‐subunit of succinyl‐CoA synthetase in the extreme acidothermophile Sulfolobus solfataricus
Solow, B. T., Bischoff, K. M., Zylka, M. J., et al. (1998) · Protein Science · doi:10.1002/pro.5560070111 · Cited by 21
Structural and Chemical Properties of ATP and Its Metal Complexes in Solution
Cohn, M. (1990) · Annals of the New York Academy of Sciences · doi:10.1111/j.1749-6632.1990.tb37669.x · Cited by 21
Causes and Consequences of Eukaryotization Through Mutualistic Endosymbiosis and Compartmentalization
Hengeveld, R., & Fedonkin, M. A. (2004) · Acta Biotheoretica · doi:10.1023/b:acbi.0000043439.34470.29 · Cited by 21
“…of the various chemical elements and compounds in the spatial temporal setting of a geologically dynamic environment; ultimately having given rise to the origin and further development of life (e.g. Pullman, 1972; Wald, 1962; Westheimer, 1987; Williams, 1981; Williams and Frausto da Silva, 1996).”
BackgroundInfluential
Biological Polymers: Evolution, Function, and Significance
Matange, K., Marland, E., Frenkel‐Pinter, M., & Williams, L. D. (2025) · Accounts of Chemical Research · doi:10.1021/acs.accounts.4c00546 · Cited by 20
“Evolution produced fragile polymers 41 − 48 that, paradoxically, dominate much of Earth’s chemistry.”
Spontane Bildung von RNA‐Strängen, Peptidyl‐RNA und Cofaktoren
Jauker, M., Griesser, H., & Richert, C. (2015) · Angewandte Chemie · doi:10.1002/ange.201506593 · Cited by 20
Lead ion induced chemodosimeter approach of a tripodal hydroxyl-quinoline based phospho-ester through P–O bond cleavage
Sain, D., Kumari, C., Kumar, A., Nayek, H. P., & Dey, S. (2016) · Dalton Transactions · doi:10.1039/c6dt00941g · Cited by 20
Monolithic Integration of Vertical Thin-Film Transistors in Nanopores for Charge Sensing of Single Biomolecules
Zhu, X., Li, X., Gu, C., et al. (2021) · ACS Nano · doi:10.1021/acsnano.1c01042 · Cited by 20
Exonucleases: Degrading DNA to Deal with Genome Damage, Cell Death, Inflammation and Cancer
Manils, J., Marruecos, L., & Soler, C. (2022) · Cells · doi:10.3390/cells11142157 · Cited by 20
“Phosphodiester (P-O) bonds are among the most versatile and stable biochemical bridges between biomolecules [2].”
Background
Friedel-Crafts-Type Acylation and Amidation Reactions in Strong Brønsted Acid: Taming Superelectrophiles
Sumita, A., & Ohwada, T. (2022) · Molecules · doi:10.3390/molecules27185984 · Cited by 20
Cyclen-based artificial nucleases: Three decades of development (1989–2022). Part a – Hydrolysis of phosphate esters
Tomczyk, M. D., Kuźnik, N., & Walczak, K. (2023) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2023.215047 · Cited by 20
Kopieren von RNA‐Sequenzen ohne Voraktivierung
Jauker, M., Griesser, H., & Richert, C. (2015) · Angewandte Chemie · doi:10.1002/ange.201506592 · Cited by 19
Spectroscopic and theoretical investigations of adenosine 5′-diphosphate and adenosine 5′-triphosphate dianions in the gas phase
Schinle, F., Crider, P. E., Vonderach, M., Weis, P., Hampe, O., & Kappes, M. M. (2012) · Physical Chemistry Chemical Physics · doi:10.1039/c2cp43808a · Cited by 21
Hydrolytic cleavage of DNA by urea-bridged macrocyclic polyamines
Li, J., Zhang, J., Lu, Q., Yue, Y., Huang, Y., Zhang, D., Lin, H., Chen, S., & Yu, X. (2009) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2009.06.030 · Cited by 20
Review of computer simulations of isotope effects on biochemical reactions: From the Bigeleisen equation to Feynman's path integral
Wong, K. Y., Xu, Y., & Xu, L. (2015) · Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics · doi:10.1016/j.bbapap.2015.04.021 · Cited by 20
HOW MANY KINDS OF PHOSPHORUS—PHOSPHORUS BONDS ARE POSSIBLE? REVIEW AND PERSPECTIVES
Christmann‐Lamande, L., Dillon, K. B., & Wolf, R. (1995) · Phosphorus, sulfur, and silicon and the related elements · doi:10.1080/10426509508027362 · Cited by 20
Experimental and Computational Evidence for a Loose Transition State in Phosphoroimidazolide Hydrolysis
Li, L., Lelyveld, V. S., Prywes, N., & Szostak, J. W. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b00784 · Cited by 21
Chemomimesis and Molecular Darwinism in Action: From Abiotic Generation of Nucleobases to Nucleosides and RNA
Saladino, R., Šponer, J. E., Šponer, J., Costanzo, G., Pino, S., & Mauro, E. D. (2018) · Life · doi:10.3390/life8020024 · Cited by 21
“The reasons why nature chose phosphate as the link to hold and maneuver genetic information have been conclusively reviewed [83].”
Background
Analysis of Phosphoryl-Transfer Enzymes with QM/MM Free Energy Simulations
Roston, D., Lu, X., Fang, D., Demapan, D., & Cui, Q. (2018) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/bs.mie.2018.05.005 · Cited by 23
“INTRODUCTION Phosphoryl transfer represents arguably one of the most important classes of biological transformations (Alberts et al., 1994; Cleland & Hengge, 2006; Kamerlin, Sharma, Prasad, & Warshel, 2013; Knowles, 1980; Lassila, Zalatan, & Herschlag, 2011; Westheimer, 1987).”
Background
Synthesis of novel aminophosphonic acids with hydantoin structure
Todorov, P., Naydenova, E. D., & Troev, K. D. (2009) · Heteroatom Chemistry · doi:10.1002/hc.20515 · Cited by 20
Escapement mechanisms: Efficient free energy transduction by reciprocally‐coupled gating
Carter, C. W. (2019) · Proteins Structure Function and Bioinformatics · doi:10.1002/prot.25856 · Cited by 20
Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds
Xu, K., Liu, L., Li, Z., et al. (2020) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.0c01557 · Cited by 20
Ground state structures of sulfate monoesters and sulfamates reveal similar reaction coordinates for sulfuryl and sulfamyl transfer
Denehy, E., White, J. M., & Williams, S. J. (2005) · Chemical Communications · doi:10.1039/b513712h · Cited by 20
Metal Ion-Catalyzed Nucleic Acid Alkylation and Fragmentation
Browne, K. A. (2002) · Journal of the American Chemical Society · doi:10.1021/ja017746x · Cited by 20
DNA cleavage promoted by Cu2+ complex of cyclen containing pyridine subunit
Li, Y., Lu, X., Sheng, X., Lu, G., Shao, Y., & Xu, Q. (2007) · Journal of Inclusion Phenomena and Macrocyclic Chemistry · doi:10.1007/s10847-007-9299-y · Cited by 20

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

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Why Nature Chose Phosphates

Abstract

Overview

Integrity signals

Verification

Claims the paper makes

Claims other papers make about this one

Citations

Cites

Cited by

Related

Metadata

Record

About these checks