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Amino acid activation with adenosine 5′-phosphorimidazolide

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Summary

Amino acids are activated by reaction with adenosine 5′-phosphorimidazolide in aqueous imidazole buffers. If adenosine 5′-(O-methylphosphate), an analogue of the 3′-terminus of t-RNA is present, 2′(3′)-O-aminoacyladenosine 5′-(O-methylphosphate) is formed. Fifteen percent of this compound accumulated at pH 5.8, but less was formed at higher pHs. The highest efficiency of utilization of ImpA attained in our experiments was about 24%. Analogous reactions occured with several other amino acids, including a number that have functional side-chains.

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Abbreviations

pA:

adenosine 5′-monophosphate

MepA:

adenosine-5′-(O-methylphosphate)

ImpA:

adenosine-5′-phosphorimidazolide

A:

adenosine

MepA-ala:

2′(3′)-O-alanyl-adenosine-5′-(O-methylphosphate)

ala-N-pA:

adenylyl-(5′ → N)-alanine

ImH:

imidazole

DKP:

diketopiperazine

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Weber, A.L., Orgel, L.E. Amino acid activation with adenosine 5′-phosphorimidazolide. J Mol Evol 11, 9–16 (1978). https://doi.org/10.1007/BF01768020

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  • DOI: https://doi.org/10.1007/BF01768020

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