Literature DB >> 7334525

Formation of pyrophosphate, tripolyphosphate, and phosphorylimidazole with the thioester, n, s-diacetyl-cysteamine, as the condensing agent.

A L Weber.   

Abstract

Reaction of 0.20M orthophosphate with 0.20M N,S-diacetylcysteamine in 0.40M imidazole at pH 7.0 or 8.0 under drying conditions at 50 degree C for 6 days yields pyrophosphate and tripolyphosphate in the presence and absence of 0.10M divalent metal ion. The efficiency of utilization of N,S-diacetylcysteamine in the formation of pyrophosphate linkages ranges from 3 - 8% under the above conditions. The thioester, N,S-diacetylcysteamine, and imidazole are required for phosphoanhydride formation. Reaction of 0.40M orthophosphate with 0.20M N,S-diacetylcysteamine in 0.40M orthophosphate with 0.20M N,S-diacetylcysteamine in 0.40M imidazole at ambient temperature for 6 days yields phosphorylimidazole in the absence or presence of 0.50M MgCl2. Phosphorylimidazole and pyrophosphate are formed in the presence of 0.05M CaCl2; pyrophosphate and tripolyphosphate are formed with 0.15M CaCl2. The efficiency of utilization of N,S-diacetylcysteamine in the formation of pyrophosphate linkages is roughly 7% at 6 days of reaction with 0.15M CaCl2. The thioester, N,S-diacetylcysteamine and imidazole are required for the formation of phosphoanhydrides. The significance of these reactions to molecular evolution is discussed.

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Year:  1981        PMID: 7334525     DOI: 10.1007/bf01733208

Source DB:  PubMed          Journal:  J Mol Evol        ISSN: 0022-2844            Impact factor:   2.395


  33 in total

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Authors:  G STEINMAN; R M LEMMON; M CALVIN
Journal:  Proc Natl Acad Sci U S A       Date:  1964-07       Impact factor: 11.205

2.  Imidazole catalysis. II. Acyl transfer and the reactions of acetyl imidazole with water and oxygen anions.

Authors:  W P JENCKS; J CARRIUOLO
Journal:  J Biol Chem       Date:  1959-05       Impact factor: 5.157

3.  THE FORMATION OF CONDENSED PHOSPHATE IN AQUEOUS SOLUTION.

Authors:  A Beck; L E Orgel
Journal:  Proc Natl Acad Sci U S A       Date:  1965-09       Impact factor: 11.205

4.  Nucleophilic attack by zinc(II)-pyridine-2-carbaldoxime anion on phosphorylimidazole. A model for enzymatic phosphate transfer.

Authors:  G J Lloyd; B S Cooperman
Journal:  J Am Chem Soc       Date:  1971-09       Impact factor: 15.419

5.  Phosphorylation by way of inorganic phosphate as a potential prebiotic process.

Authors:  J Rabinowitz; S Chang; C Ponnamperuma
Journal:  Nature       Date:  1968-05-04       Impact factor: 49.962

6.  Intramolecular catalysis of acylation and deacylation in peptides containing cysteine and histidine.

Authors:  M J Heller; J A Walder; I M Klotz
Journal:  J Am Chem Soc       Date:  1977-04-13       Impact factor: 15.419

7.  Formation of the imidazolides of dinucleotides under potentially prebiotic conditions.

Authors:  H L Sleeper; R Lohrmann; L E Orgel
Journal:  J Mol Evol       Date:  1978-06-20       Impact factor: 2.395

8.  Phosphorus, a key to life on the primitive Earth.

Authors:  E J Griffith; C Ponnamperuma; N W Gabel
Journal:  Orig Life       Date:  1977-08

9.  Prebiotic condensation reactions in an aqueous medium: a review of condensing agents.

Authors:  J Hulshof; C Ponnamperuma
Journal:  Orig Life       Date:  1976-08

10.  Formation of nucleoside 5'-phosphoramidates under potentially prebiological conditions.

Authors:  R Lohrmann
Journal:  J Mol Evol       Date:  1977-11-25       Impact factor: 2.395

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  29 in total

1.  Origin of fatty acid synthesis: thermodynamics and kinetics of reaction pathways.

Authors:  A L Weber
Journal:  J Mol Evol       Date:  1991       Impact factor: 2.395

2.  Oligoglyceric acid synthesis by autocondensation of glyceroyl thioester.

Authors:  A L Weber
Journal:  J Mol Evol       Date:  1987       Impact factor: 2.395

3.  Prebiotic formation of 'energy-rich' thioesters from glyceraldehyde and N-acetylcysteine.

Authors:  A L Weber
Journal:  Orig Life Evol Biosph       Date:  1984       Impact factor: 1.950

4.  Alanine synthesis from glyceraldehyde and ammonium ion in aqueous solution.

Authors:  A L Weber
Journal:  J Mol Evol       Date:  1985       Impact factor: 2.395

5.  Chemical constraints governing the origin of metabolism: the thermodynamic landscape of carbon group transformations under mild aqueous conditions.

Authors:  Arthur L Weber
Journal:  Orig Life Evol Biosph       Date:  2002-08       Impact factor: 1.950

Review 6.  On the origin of biochemistry at an alkaline hydrothermal vent.

Authors:  William Martin; Michael J Russell
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2007-10-29       Impact factor: 6.237

7.  Adsorption of 5'-adenosine monophosphate onto precipitated calcium phosphate: effects of inorganic polyphosphates and carbamyl phosphate.

Authors:  M Hermes-Lima; A C Tessis; A Vieyra
Journal:  Orig Life Evol Biosph       Date:  1990       Impact factor: 1.950

8.  The triose model: glyceraldehyde as a source of energy and monomers for prebiotic condensation reactions.

Authors:  A L Weber
Journal:  Orig Life Evol Biosph       Date:  1987       Impact factor: 1.950

9.  Nonenzymatic formation of "energy-rich" lactoyl and glyceroyl thioesters from glyceraldehyde and a thiol.

Authors:  A L Weber
Journal:  J Mol Evol       Date:  1984       Impact factor: 2.395

10.  Thiol-catalyzed formation of lactate and glycerate from glyceraldehyde.

Authors:  A L Weber
Journal:  J Mol Evol       Date:  1983       Impact factor: 2.395

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