Abstract
We have recently shown that 2-aminoimidazole is a superior nucleotide activating group for nonenzymatic RNA copying. Here we describe a prebiotic synthesis of 2-aminoimidazole that shares a common mechanistic pathway with that of 2-aminooxazole, a previously described key intermediate in prebiotic nucleotide synthesis. In the presence of glycolaldehyde, cyanamide, phosphate and ammonium ion, both 2-aminoimidazole and 2-aminooxazole are produced, with higher concentrations of ammonium ion and acidic pH favoring the former. Given a 1:1 mixture of 2-aminoimidazole and 2-aminooxazole, glyceraldehyde preferentially reacts and cyclizes with the latter, forming a mixture of pentose aminooxazolines, and leaving free 2-aminoimidazole available for nucleotide activation. The common synthetic origin of 2-aminoimidazole and 2-aminooxazole and their distinct reactivities are suggestive of a reaction network that could lead to both the synthesis of RNA monomers and to their subsequent chemical activation.
| Original language | English |
|---|---|
| Pages (from-to) | 8780-8783 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 139 |
| Issue number | 26 |
| DOIs | |
| Publication status | Published - 2017 Jul 5 |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Common and Potentially Prebiotic Origin for Precursors of Nucleotide Synthesis and Activation. / Fahrenbach, Albert C.; Giurgiu, Constantin; Tam, Chun Pong; Li, Li; Hongo, Yayoi; Aono, Masashi; Szostak, Jack W.
In: Journal of the American Chemical Society, Vol. 139, No. 26, 05.07.2017, p. 8780-8783.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Common and Potentially Prebiotic Origin for Precursors of Nucleotide Synthesis and Activation
AU - Fahrenbach, Albert C.
AU - Giurgiu, Constantin
AU - Tam, Chun Pong
AU - Li, Li
AU - Hongo, Yayoi
AU - Aono, Masashi
AU - Szostak, Jack W.
PY - 2017/7/5
Y1 - 2017/7/5
N2 - We have recently shown that 2-aminoimidazole is a superior nucleotide activating group for nonenzymatic RNA copying. Here we describe a prebiotic synthesis of 2-aminoimidazole that shares a common mechanistic pathway with that of 2-aminooxazole, a previously described key intermediate in prebiotic nucleotide synthesis. In the presence of glycolaldehyde, cyanamide, phosphate and ammonium ion, both 2-aminoimidazole and 2-aminooxazole are produced, with higher concentrations of ammonium ion and acidic pH favoring the former. Given a 1:1 mixture of 2-aminoimidazole and 2-aminooxazole, glyceraldehyde preferentially reacts and cyclizes with the latter, forming a mixture of pentose aminooxazolines, and leaving free 2-aminoimidazole available for nucleotide activation. The common synthetic origin of 2-aminoimidazole and 2-aminooxazole and their distinct reactivities are suggestive of a reaction network that could lead to both the synthesis of RNA monomers and to their subsequent chemical activation.
AB - We have recently shown that 2-aminoimidazole is a superior nucleotide activating group for nonenzymatic RNA copying. Here we describe a prebiotic synthesis of 2-aminoimidazole that shares a common mechanistic pathway with that of 2-aminooxazole, a previously described key intermediate in prebiotic nucleotide synthesis. In the presence of glycolaldehyde, cyanamide, phosphate and ammonium ion, both 2-aminoimidazole and 2-aminooxazole are produced, with higher concentrations of ammonium ion and acidic pH favoring the former. Given a 1:1 mixture of 2-aminoimidazole and 2-aminooxazole, glyceraldehyde preferentially reacts and cyclizes with the latter, forming a mixture of pentose aminooxazolines, and leaving free 2-aminoimidazole available for nucleotide activation. The common synthetic origin of 2-aminoimidazole and 2-aminooxazole and their distinct reactivities are suggestive of a reaction network that could lead to both the synthesis of RNA monomers and to their subsequent chemical activation.
UR - http://www.scopus.com/inward/record.url?scp=85021993795&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85021993795&partnerID=8YFLogxK
U2 - 10.1021/jacs.7b01562
DO - 10.1021/jacs.7b01562
M3 - Article
C2 - 28640999
AN - SCOPUS:85021993795
VL - 139
SP - 8780
EP - 8783
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 26
ER -