Abstract
We have used gel electrophoresis to study the primary covalent addition of amino acids to oligonucleotides or their analogs and the subsequent addition of further molecules of the amino acids to generate peptides covalently linked to the oligonucleotides. We have surveyed the reactions of a variety of amino acids with the phosphoramidates derived from oligonucleotide 5′-phosphates and ethylenediamine. We find that arginine and amino acids that can interact with oligonucleotides through stacking interactions react most efficiently. D-and L-amino acids give indistinguishable families of products.
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Ben Cheikh A, Orgel LE (1990) Polymerization of amino acids containing nucleotide bases. J Mol Evol 30:315–321
Chu BCF, Orgel LE (1985) Detection of specific DNA sequences with short biotin-labeled probes. DNA 4(4):327–331
Ehler KW (1976) Reactions of carbamylimidazoles with nucleophiles-an example of an intramolecular acyl transfer reaction. J Org Chem 41(18):3041–3042
Ehler KW, Orgel LE (1976) N,N′-carbonyldiimidazole-induced peptide formation in aqueous solution. Biochim Biophys Acta 434: 233–243
Lacey Jr JC, Wickramasinghe NSMD, Cook GW (1992) Experimental studies on the origin of the genetic code and the process of protein synthesis: a review update. Orig Life Evol Biosph 22(5):243–275
Maniatis T, Fritsch EF, Sambrook J (1982) Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York
Pinck M, Schuber F (1971) Reaction of tris-(hydroxymethyl)-aminomethane with valyl-TYMV-RNA. Biochimie 53:887–891
Weber AL, Orgel LE (1980) Poly(U)-directed peptide-bond formation from the 2′(3′)-glycyl esters of adenosine derivatives. J Mol Evol 16(1):1–10
Wolfenden R (1963) The mechanism of hydrolysis of amino acyl RNA. Biochemistry 2(5):1090–1092
Zachau HG, Feldmann H (1965) Amino acid esters of RNA, nucleosides and related compounds. Prog Nucleic Acid Res Mol Biol 4:217–230
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Correspondence to: L.E. Orgel 1444
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Zieboll, G., Orgel, L.E. The use of gel electrophoresis to study the reactions of activated amino acids with oligonucleotides. J Mol Evol 38, 561–565 (1994). https://doi.org/10.1007/BF00175875
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DOI: https://doi.org/10.1007/BF00175875