Spontaneous formation and base pairing of plausible prebiotic nucleotides in water.
The RNA World hypothesis presupposes that abiotic reactions originally produced nucleotides, the monomers of RNA and universal constituents of metabolism. However, compatible prebiotic reactions for the synthesis of complementary (that is, base pairing) nucleotides and mechanisms for their mutual selection within a complex chemical environment have not been reported. Here we show that two plausible prebiotic heterocycles, melamine and barbituric acid, form glycosidic linkages with ribose and ribose-5-phosphate in water to produce nucleosides and nucleotides in good yields. Even without purification, these nucleotides base pair in aqueous solution to create linear supramolecular assemblies containing thousands of ordered nucleotides. Nucleotide anomerization and supramolecular assemblies favour the biologically relevant β-anomer form of these ribonucleotides, revealing abiotic mechanisms by which nucleotide structure and configuration could have been originally favoured. These findings indicate that nucleotide formation and selection may have been robust processes on the prebiotic Earth, if other nucleobases preceded those of extant life.
School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, Georgia 30332, USA.|NSF-NASA Center for Chemical Evolution, Atlanta, Georgia 30332, USA.
Brian J
BJ
Cafferty
School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, Georgia 30332, USA.|NSF-NASA Center for Chemical Evolution, Atlanta, Georgia 30332, USA.
David M
DM
Fialho
School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, Georgia 30332, USA.|NSF-NASA Center for Chemical Evolution, Atlanta, Georgia 30332, USA.
Jaheda
J
Khanam
NSF-NASA Center for Chemical Evolution, Atlanta, Georgia 30332, USA.|Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
Ramanarayanan
0000-0001-5238-610X
R
Krishnamurthy
School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, Georgia 30332, USA.|NSF-NASA Center for Chemical Evolution, Atlanta, Georgia 30332, USA.
Nicholas V
NV
Hud
D001463:Barbiturates / Q000737:chemistry*; D020029:Base Pairing; D019418:Evolution, Chemical; D006031:Glycosylation; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D009711:Nucleotides / Q000737:chemistry*; D000069497:Origin of Life; D056692:Prebiotics; D012313:RNA / Q000737:chemistry; D012265:Ribonucleotides / Q000737:chemistry; D012267:Ribosemonophosphates / Q000737:chemistry; D014227:Triazines / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D001463:Barbiturates; D009705:Nucleosides; D009711:Nucleotides; D056692:Prebiotics; D012265:Ribonucleotides; D012267:Ribosemonophosphates; D014227:Triazines; D014867:Water; C031626:ribose-5-phosphate; D012313:RNA; C011907:melamine; C032232:barbituric acid