Formation of pyrophosphate, tripolyphosphate, and phosphorylimidazole with the thioester, N, S-diacetylcysteamine, as the condensing agent
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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Weber reported the non-enzymatic synthesis of acyl phosphates from a thioester in the presence of phosphate during the synthesis of pyrophosphate from thioesters.
“Weber [81] reported the non-enzymatic synthesis of acyl phosphates from a thioester in the presence of phosphate during the synthesis of pyrophosphate from thioesters, although the acyl phosphate itself was not isolated.”
From Early bioenergetic evolution (2013) · cites this paper as [81]
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- Authors
- Weber, A. L.
- Affiliations
- Salk Institute for Biological Studies (US)
- Corresponding author
- Weber, Arthur L.
- Venue
- Journal of Molecular Evolution
- Published
- 1981-01
- Volume
- 18
- Issue
- 1
- Pages
- 24-29
- ISSN
- 0022-2844 (ISSN-L)
- 1432-1432
- OpenAlex
- W2022124456
- Cited by
- 61
- References
- 56
- Citations by year
- 2025: 3 · 2024: 2 · 2023: 1 · 2022: 1 · 2021: 3 · 2020: 4 · 2018: 1 · 2017: 3 · 2013: 4 · 2012: 1
- FWCI
- 3.68
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Journal of Molecular Evolution (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Organophosphorus compounds synthesis
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biochemical and Molecular Research
- Keywords
- pyrophosphate formation, tripolyphosphate, orthophosphate, imidazole, divalent metal ions, magnesium, calcium, phosphorus metabolism, origin of life, molecular evolution
- MeSH terms
- Cations, Divalent, Chromatography, Paper, Cysteamine, Biological Evolution, Imidazoles, Polyphosphates, Time Factors
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