The role of the formamide/zirconia system in the synthesis of nucleobases and biogenic carboxylic acid derivatives.
We describe the one-pot synthesis of a large variety of nucleic acid bases and related compounds from formamide in the presence of zirconium minerals as catalysts. The major products observed are: purine, 2-hydroxy pyrimidine, 5-hydroxy pyrimidine, isocytosine, adenine, urea, and carbodiimide. The synthesis of low molecular weight amides and carboxylic acid derivatives (intermediates of extant metabolism) was also observed: glyoxylamide, glycolic-, lactic-, succinic-, oxalic-, fumaric-, and maleic acids. As the major problem in the origin of informational polymers is the instability of their precursors, we also investigated the effects of zirconia minerals on the stability of ribooligonucleotides in formamide and in water. The relevance of these findings with respect to the origin of informational polymers and primordial metabolism is discussed.
Saladino
Raffaele
R
Dipartimento A.B.A.C., Università della Tuscia, Via San Camillo De Lellis, 01100, Viterbo, Italy. saladino@unitus.it
Neri
Veronica
V
Crestini
Claudia
C
Costanzo
Giovanna
G
Graciotti
Michele
M
Di Mauro
Ernesto
E
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004355:Drug Stability; D005559:Formamides / Q000494:pharmacology*; D008954:Models, Biological; D008970:Molecular Weight; D009696:Nucleic Acids / Q000138:chemical synthesis; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000737:chemistry; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D020871:RNA Stability / Q000187:drug effects; D014867:Water / Q000494:pharmacology; D015040:Zirconium / Q000494:pharmacology*
D000577:Amides; D002264:Carboxylic Acids; D005559:Formamides; D009696:Nucleic Acids; D009930:Organic Chemicals; D011687:Purines; D011743:Pyrimidines; D014867:Water; C031066:formamide; D015040:Zirconium; C030986:pyrimidine; C028541:zirconium oxide