Peptide Formation in the Presence of Linear or Cyclic Polyphosphates

Rabinowitz, J.; Flores, José Juan Alvarado; Kresbach, R; Rogers, Glenn E.

doi:10.1038/224795a0

Cited by 118 publications

(45 citation statements)

References 18 publications

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“…However, it seems more likely to us that the chemical evolution might have taken place in the primitive oceans as a more universal place where peptides were formed from amino acids with an aid of various condensing agents and were accumulated gradually against their hydrolysis under mild conditions. Several simulation experiments were performed from such a viewpoint in aqueous solutions containing condensing agents (Steinman et al, t964, 1966;Rabinowitz et al, 1969;Chung et al, 1971;Rabinowitz and Hampei, 1978;Hawker and Oro, 1981;Sakurai and Yanagawa, 1984;Yamanaka et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

Diketopiperazine-mediated peptide formation in aqueous solution

Nagayama

Takaoka

Inomata

et al. 1990

Origins Life Evol Biosphere

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Though diketopiperazines (DKP) are formed in most experiments concerning the prebiotic peptide formation, the molecules have not been paid attention in the studies of chemical evolution. We have found that triglycine, tetraglycine or pentaglycine are formed in aqueous solution of glycine anhydride (DKP) and glycine, diglycine or triglycine, respectively. A reaction of alanine with DKP resulted in the formation of glycylglycylalanine under the same conditions. These results indicate that the formation of the peptide bonds proceeds through the nucleophilic attack of an amino group of the amino acids or the oligoglycines on the DKP accompanied by the ring-opening. The formation of glycine anhydride, di-, tri- and tetraglycine was also observed in a mixed aqueous solution of urea and glycine in an open system to allow the evaporation of ammonia. A probable pathway is proposed for prebiotic peptide formation through diketopiperazine on the primitive Earth.

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Section: Introductionmentioning

confidence: 99%

Diketopiperazine-mediated peptide formation in aqueous solution

Nagayama

Takaoka

Inomata

et al. 1990

Origins Life Evol Biosphere

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“…Another idea to form peptides is the use of condensation agents such as cyanamides [78,79], cyanates [80], trimetaphosphate [81], ATP [82], GTP, CTP, UTP [83], linear [84] and cyclic [85] inorganic polyphosphates [86], and imidazoles [87][88][89]13]. Since the reaction medium is aqueous though, these condensation agents would hydrolyze or decompose quickly, especially at the elevated temperatures prevailing in the prebiotic "soup".…”

Section: Peptidesmentioning

confidence: 99%

Prebiotic Chemistry: The Amino Acid and Peptide World

Plankensteiner¹,

Reiner²,

Rode

2005

COC

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In this review the idea of a "Peptide/Protein World" preceding the widely rooted idea of the "RNA world" is presented and elaborated. To support this idea, the formation of the building blocks of nucleic acids and peptides and their assembly to biopolymers in a primordial earth scenario is discussed. Furthermore, chemical stability problems of the building blocks and the assembled biomolecules are presented, and finally their ability to efficiently replicate and chemically evolve is argued. Taking into account various problems in all these areas for nucleic acids and nucleotides, the idea of the "Peptide/Protein World" is brought up, stating that peptides and proteins would have come first in chemical evolution with an "RNA world" appearing only later with the protective help of protein shells.

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“…Rabinowitz et al first reported that diglycine is formed in good yield, when glycine is maintained in alkaline solution in the presence of a high concentration of sodium trimetaphosphate [2]. The reaction was subsequently shown to proceed via diglycine Nphosphate (Scheme 1).…”

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confidence: 96%

Trimetaphosphate‐Induced Addition of Aspartic Acid to Oligo(glutamic acid)s

Hill

Orgel

2002

Helvetica Chimica Acta

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Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday When a solution containing 0.01m decaglutamic acid, 0.1 ± 1.0m aspartic acid, 1.0m MgCl 2 , and 0.5m sodium trimetaphosphate is allowed to stand at temperatures in the range 0 ± 508, addition products containing up to ten aspartic acid residues are formed. Addition occurs to the side-chain carboxy moieties, not to the terminal amine of the decaglutamic acid. A number of other amino acids including glutamic acid, glycine, and histidine fail to react with decaglutamic acid under the same conditions. We believe that the activation of aspartic acid leads to the formation of a cyclic anhydride that is the key intermediate in the reaction.

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Peptide Formation in the Presence of Linear or Cyclic Polyphosphates

Cited by 118 publications

References 18 publications

Diketopiperazine-mediated peptide formation in aqueous solution

Diketopiperazine-mediated peptide formation in aqueous solution

Prebiotic Chemistry: The Amino Acid and Peptide World

Trimetaphosphate‐Induced Addition of Aspartic Acid to Oligo(glutamic acid)s

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