Abstract
We have studied the oligomerization of an activated, achiral nucleotide analogue related to the pyrimidine barbituric acid in the absence and in the presence of a complementary, pyrophosphate-linked oligomer. Although no template-directed catalysis of the oligomerization was observed with water as solvent, catalysis of the oligomerization was demonstrated in a mixture of dimethylformamide with water. Poly(U) also stimulated the oligomerization, but was less effective than the analogue. Environments in which similar effects may be observed, and some potential implications for prebiotic chemistry, are discussed.
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References
Branda N, Wyler R, Rebek Jr J (1994) Encapsulation of methane and other small molecules in a self-assembling superstructure. Science 263:1267–1268
Chang S-K, Van Engen D, Fan E, Hamilton AD (1991) Hydrogen bonding and molecular recognition: synthetic, complexation, and structural studies on barbiturate binding to an artificial receptor. J Am Chem Soc 113:7640–7645
Deamer DW, Pashley RM (1989) Amphiphilic components of the Murchison carbonaceous chondrite: surface properties and membrane formation. Origins Life 19:21–38
Eigen M, Gardiner W, Schuster P, Winkler-Oswatitsch R (1981) The origin of genetic information. Sci Am 244:88–108
Fox SW, Dose K (1972) Molecular evolution and the origin of life. Marcel Dekker, New York
Huang WM, Tsò POP (1966) Physiochemical basis of the recognition process in nucleic acid interactions. I. Interactions of polyuridylic acid and nucleosides. J Mol Biol 16:523–543
Hill AR Jr, Orgel LE, Wu T (1993) The limits of template-directed synthesis with nucleoside-5′-phosphoro(2-methyl)imidazolides. Origins Life 23:285–290
Inoue T, Orgel LE (1982) Oligomerization of (guanosine 5′-phosphor)-2-methylimidazolide on poly(C). An RNA polymerase model. J Mol Biol 162:201–217
Jorgensen WL, Severance DL (1991) Chemical chameleons: hydrogen bonding with imides and lactams in chloroform. J Am Chem Soc 113:209–216
Joyce GF, Orgel LE (1993) Prospects for understanding the origin of the RNA world. In: Gesteland RF, Atkins JF (eds) The RNA world. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
Kelly TR, Zhao C, Bridger GJ (1989) A bisubstrate reaction template. J Am Chem Soc 111:3744–3745
Kurihara K, Ohto K, Honda Y, Kunitake T (1991) Efficient, complementary binding of nucleic acid bases to diaminotriazinefunctionalized monolayers on water. J Am Chem Soc 113:5077–5079
Lehn J-M, Mascal M, DeCian A, Fischer J (1990) Molecular recognition directed self-assembly of ordered supramolecular strands by cocrystallization of complementary molecular components. J Chem Soc Chem Commun 1990:479–481
Miles HT, Frazier J (1982) Infrared study of G · C complex formation in template-dependent oligo(G) synthesis. J Mol Evol 162:219–230
Murray TJ, Zimmerman SC (1992) New triply hydrogen bonded complexes with highly variable stabilities. J Am Chem Soc 114:4010–4011
Nowick JS, Chen JS, Noronha G (1993) Molecular recognition in micelles: the roles of hydrogen bonding and hydrophobicity in adenine-thymine base-pairing in SDS micelles. J Am Chem Soc 115:7636–7644
Oparin Al (1957) The origin of life on the earth. Oliver and Boyd, London
Petersen SB, Led JJ (1981) Watson-Crick base pairing between guanosine and cytidine studied by13C nuclear magnetic resonance. J Am Chem Soc 103:5308–5313
Seto CT, Whitesides GM (1990) Self-assembly based on the cyanuric acid-melamine lattice. J Am Chem Soc 112:6409–6411
Stribling R, Miller SL (1991) Attempted nonenzymatic template-directed oligomerizations on a polyadenylic acid template: implications for the nature of the first genetic material. J Mol Evol 32:282–288
Terfort A, Kiedrowski GV (1992) Selbstreplikation bei der Kondensation von 3-Aminobenzamidinen mit 2-Formylphenoxessigsaeuren. Angew Chem 104:626–627
Tjivikua T, Ballester P, Rebek J Jr (1990) A self-replicating system. J Am Chem Soc 112:1249–1250
Van Vliet MJ, Visscher J, Schwartz AW (1994a) Achiral nucleoside analogs: 5,5-disubstituted pyrimidines related to barbituric acid. Nucleosides Nucleotides 13:2113–2124
Van Vliet MJ, Visscher J, Schwartz AW (1994b) An achiral (oligo) nucleotide analog. J Mol Evol 38:438–442
Visscher J, Schwartz AW (1988) Template-directed synthesis of acyclic oligonucleotide analogs. J Mol Evol 28:3–6
Walde P, Goto A, Monnard P-A, Wessicken M, Luisi PL (1994) Oparin's reactions revisited: enzymatic synthesis of poly(adenylic acid) in micelles and self-reproducing vesicles. J Am Chem Soc 116:7541–7547
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Correspondence to: A.W. Schwartz.
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van Vliet, M.J., Visscher, J. & Schwartz, A.W. Hydrogen bonding in the template-directed oligomerization of a pyrimidine nucleotide analogue. J Mol Evol 41, 257–261 (1995). https://doi.org/10.1007/BF01215172
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DOI: https://doi.org/10.1007/BF01215172