Recherches sur la formation et la transformation des esters LXXXIII [1]. Réactions de condensation et/ou de phosphorylation, en solution aqueuse, de divers composés organiques à fonctions OH, COOH, NH2, ou autres, à l'aide de polyphosphates linéaires ou cycliques
Abstract
Amino acids and other derivatives are condensed in aqueous solutions in the presence of linear or cyclic polyphosphates (or other anhydrides of P acids). The best results are obtained in slightly alkaline media (pH 7.5 to 9.5). The reaction, which has been studied at 70°C and at room temperature, proceeds with relative ease even at room temperature. In the case of the cyclic polyphosphates, trimetaphosphate gave the best results as compared with tetra‐ and hexametaphosphate, and among the linear polyphosphates used the yields grew with the average length of the chain.
The significance of this method of condensation as a general method and also in the context of chemical evolution is discussed.
The author suggests that one of the pathways leading to the peptide bond formation involves the intermediate formation of aminoacyl phosphates or polyphosphates by the nucleophilic attack of the carboxylate group of the amino acid on the phosphorus of a linear or cyclic POP bond, giving rise to the labile mixed anhydride, and subsequent nucleophilic attack of the amino nitrogen of a molecule of the amino acid, or of the aminoacyl phosphate already produced, on the C of the mixed anhydride with displacement of phosphate or polyphosphate and formation of a peptide bond. Other pathways may also involve the intermediate formation of phosphoramidates which may result from the reaction of amino groups (or ammonia) with trimetaphosphate in alkaline medium.
Linear and cyclic polyphosphates (which are known to be phosphorylating agents of the OH (alcoholic) function in aqueous solutions at pH's above 7) phosphorylate serine, ethanolamine and threonine in aqueous solutions at pH 8–10 with yields up to 25%.
Number of times cited: 24
- Christian Fernández-García, Adam J. Coggins and Matthew W. Powner, A Chemist’s Perspective on the Role of Phosphorus at the Origins of Life, Life, 7, 3, (31), (2017).
- Hideko Maeda, Mako Katsushiro, Hiroyuki Nariai and Hirokazu Nakayama, INTRODUCTION OF PHOSPHATE GROUP INTO β-ARBUTIN BY CYCLO-TRIPHOSPHATE, Phosphorus Research Bulletin, 33, 0, (21), (2017).
- Yanchun Cao, Shuxia Cao, Yali Xie, Xiangkun Zong and Yufen Zhao, Investigation of Reaction Mechanism of Amino Acids and Phosphorus Trichloride by 31P NMR and ESI‐MS/MS, Chinese Journal of Chemistry, 29, 6, (1173-1179), (2011).
- Yang Jiang, Bo Tan, Zhong‐Zhou Chen, Tong Liu, Ru‐Gang Zhong, Yan‐Mei Li, David Jeremy Stewart, Yu‐Fen Zhao and Hua‐Liang Jiang, Phosphoryl group differentiating α‐amino acids from β‐ and γ‐amino acids in prebiotic peptide formation, International Journal of Quantum Chemistry, 94, 4, (232-241), (2003).
- Yang Jiang, Ru-Gang Zhong, Bo Tan, Yan-Mei Li and Yu-Fen Zhao, Recognition of α-Amino Acid from β- and γ-Amino Acid by N -Phosphorylation, Phosphorus, Sulfur, and Silicon and the Related Elements, 10.1080/10426500307806, 178, 4, (831-837), (2003).
- Junpei Yamanaka, Katsuhiko Inomata and Yukio Yamagata, Condensation of oligoglycines with trimeta- and tetrametaphosphate in aqueous solutions, Origins of Life and Evolution of the Biosphere, 18, 3, (165), (1988).
- Mitsutomo Tsuhako, Chiyoko Sueyoshi, Yoshinobu Baba, Tohoru Miyajima, Shigeru Ohashi and Hiroyuki Nariai, Phosphorylation of Glucose withcyclo-Triphosphate, Chemistry Letters, 16, 7, (1431), (1987).
- Mitsutomo Tsuhako, Chiyoko Sueyoshi, Tohru Miyajima, Shigeru Ohashi, Hiroyuki Nariai and Itaru Motooka, The Reaction ofcyclo-Triphosphate with Ethanolamines, Bulletin of the Chemical Society of Japan, 59, 10, (3091), (1986).
- Mitsutomo Tsuhako, Akemi Nakajima, Tohru Miyajima, Shigeru Ohashi, Hiroyuki Nariai and Itaru Motooka, The Reaction ofcyclo-Triphosphate with L-α- or β-Alanine, Bulletin of the Chemical Society of Japan, 58, 11, (3092), (1985).
- Mitsutomo Tsuhako, Akiko Nakahama, Shigeru Ohashi, Hiroyuki Nariai and Itaru Motooka, The Reaction ofcyclo-Triphosphate with Ethylenediamine, Bulletin of the Chemical Society of Japan, 56, 5, (1372), (1983).
- Joseph Rabinowitz and Aioub Hampai, , Helvetica Chimica Acta, 63, 4, (962-966), (2004).
- Joseph Rabinowitz and Aioub Hampai, Influence of Imidazole and Hydrocyanic Acid Derivatives on the ‘Possible Prebiotic’ polyphosphate induced peptide synthesis in aqueous solution, Helvetica Chimica Acta, 61, 5, (1842-1847), (2004).
- Jos�e Hulshof and Cyril Ponnamperuma, Prebiotic condensation reactions in an aqueous medium: A review of condensing agents, Origins of Life, 7, 3, (197), (1976).
- J. Or� and E. Stephen-Sherwood, Abiotic origin of biopolymers, Origins of Life, 7, 1, (37), (1976).
- H. Sawai and L. E. Orgel, Prebiotic peptide-formation in the solid state, Journal of Molecular Evolution, 6, 3, (185), (1975).
- E. Stephen-Sherwood and J. Oró, Chemical evolution, recent syntheses of bioorganic molecules, Space Life Sciences, 4, 1, (5), (1973).
- R. LOHRMANN and L. E. ORGEL, Prebiotic Activation Processes, Nature, 244, 5416, (418), (1973).
- Joseph Rabinowitz, Note on the rôle of cyanides and polyphosphates in the formation of peptides in aqueous solutions of amino acids, at room temperature, as a possible prebiotic process, Helvetica Chimica Acta, 54, 5, (1483-1485), (2004).
- N.M. Chung, R. Lohrmann, L.E. Orgel and J. Rabinowitz, The mechanism of the trimetaphosphate-induced peptide synthesis, Tetrahedron, 27, 6, (1205), (1971).
- Joseph Rabinowitz, , Helvetica Chimica Acta, 53, 1, (53-63), (2004).
- Joseph Rabinowitz, Peptide and Amide Bond Formation in Aqueous Solutions of Cyclic or Linear Polyphosphates as a possible prebiotic process, Helvetica Chimica Acta, 53, 6, (1350-1355), (2004).
- JOSEPH RABINOWITZ, ChemInform Abstract: DARST. UND UMLAGERUNG VON ESTERN 83. MITT. KONDENSATIONSRK. UND/ODER PHOSPHORYLIERUNG VON ORGANISCHEN VERBINDUNGEN MIT OH-, COOH-, NH2- ODER ANDEREN FUNKTIONEN MITTELS LINEARER ODER CYCLISCHER POLYPHOSPHATE IN WAESSRIGER LOESUNG, Chemischer Informationsdienst. Organische Chemie, 1, 10, (no), (1970).
- E. Cherbuliez, Br. Baehler, J. Marszalek, G. Weber and J. Rabinowitz, , Helvetica Chimica Acta, 52, 8, (2676-2679), (2004).
- Megha Karki, Clémentine Gibard, Subhendu Bhowmik and Ramanarayanan Krishnamurthy, Nitrogenous Derivatives of Phosphorus and the Origins of Life: Plausible Prebiotic Phosphorylating Agents in Water, Life, 10.3390/life7030032, 7, 3, (32), (2017).
