Summary
Adenosine 5′-phosphoramidates form when solutions containing adenosine 5′-polyphosphates pnA (n ≧ 3) or P1, P2-diadenosine 5′-diphosphate and amines are allowed to dry out. Mg ions catalyze these reactions. We have studied systems containing ammonia, imidazole, glycine, ethylenediamine and histamine. The yields of adenosine 5′-phosphoramidates range from 10–50 % based on the nucleotide. The prebiotic significance of the reactions is discussed.
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Abbreviations
- Im:
-
imidazole
- hist:
-
histamine
- gly:
-
glycine
- en:
-
ethylenediamine
- CDI:
-
1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride
- EDTA:
-
ethylenediaminetetraacetic acid
- A:
-
adenosine
- Pn (n = 1, 2 ⋯):
-
linear polyphosphate containing n phosphate residues
- pnA:
-
adenosine 5′-polyphosphate containing n phosphate residues
- ADP:
-
adenosine 5′-diphosphate
- ATP:
-
adenosine 5′-triphosphate
- AppA:
-
P1, P2-diadenosine 5′-diphosphate
- gly-pA:
-
adenylyl-(5′→N)-glycine
- ImpA:
-
adenosine 5′-phosphorimidazolide
- NH2-pA:
-
adenosine 5′-phosphoramidate
- en-pA:
-
adenylyl-(5′→N)-ethylenediamine
- hist (NH) - pA:
-
adenosine 5′-phospho-[2-(4-imidazolyl)-ethylamide]
- hist(Im)-pA:
-
adenosine 5′-phospho-[4-(2-aminoethyl)-imidazolide]
- enP1,2 :
-
phosphoramidates of ethylenediamine derived from H3PO4 and H4P2O7
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Lohrmann, R. Formation of nucleoside 5′-phosphoramidates under potentially prebiological conditions. J Mol Evol 10, 137–154 (1977). https://doi.org/10.1007/BF01751807
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DOI: https://doi.org/10.1007/BF01751807