New Catalytic Asymmetric Formation of Oxygen Heterocycles Bearing Nucleoside Bases at the Anomeric Carbon

2019 ◽  
Vol 141 (26) ◽  
pp. 10199-10204 ◽  
Author(s):  
Barry M. Trost ◽  
Shiyan Xu ◽  
Ehesan U. Sharif
Keyword(s):  
Oxygen Heterocycles ◽  
Anomeric Carbon ◽  
Catalytic Asymmetric

A common precursor to both prebiotic and biological pathways to RNA nucleotides

2018 ◽  
Author(s):  
Andrea Pérez-Villa ◽  
Thomas Georgelin ◽  
Jean-François Lambert ◽  
Marie-Christine Maurel ◽  
François Guyot ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
De Novo ◽  
Life Forms ◽  
Hydrothermal Conditions ◽  
Modern Life ◽  
Ab Initio Simulations ◽  
Spontaneous Formation ◽  
Common Precursor ◽  
Open Issue ◽  
Anomeric Carbon

Understanding the mechanism of spontaneous formation of ribonucleotides under realistic prebiotic conditions is a key open issue of origins-of-life research. In cells, <i>de novo</i> and salvage nucleotide enzymatic synthesis combines 5-phospho-α -D-ribose-1-diphosphate ( α-PRPP) and nucleobases. Interestingly, these reactants are also known as prebiotically plausible compounds. Combining ab initio simulations with mass spectrometry experiments, we compellingly demonstrate that nucleobases and α -PRPP spontaneously combine, through the same facile mechanism, forming both purine and pyrimidine ribonucleotides, under mild hydrothermal conditions. Surprisingly, this mechanism is very similar to the biological one, and yields ribonucleotides with the same anomeric carbon chirality as in biological systems. These results suggest that natural selection might have optimized – through enzymes – a pre-existing ribonucleotide formation mechanism, carrying it forward to modern life forms.

A common precursor to both prebiotic and biological pathways to RNA nucleotides

2017 ◽  
Author(s):  
Andrea Pérez-Villa ◽  
Thomas Georgelin ◽  
Jean-François Lambert ◽  
Marie-Christine Maurel ◽  
François Guyot ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
De Novo ◽  
Life Forms ◽  
Hydrothermal Conditions ◽  
Modern Life ◽  
Ab Initio Simulations ◽  
Spontaneous Formation ◽  
Common Precursor ◽  
Open Issue ◽  
Anomeric Carbon

Understanding the mechanism of spontaneous formation of ribonucleotides under realistic prebiotic conditions is a key open issue of origins-of-life research. In cells, <i>de novo</i> and salvage nucleotide enzymatic synthesis combines 5-phospho-α -D-ribose-1-diphosphate ( α-PRPP) and nucleobases. Interestingly, these reactants are also known as prebiotically plausible compounds. Combining ab initio simulations with mass spectrometry experiments, we compellingly demonstrate that nucleobases and α -PRPP spontaneously combine, through the same facile mechanism, forming both purine and pyrimidine ribonucleotides, under mild hydrothermal conditions. Surprisingly, this mechanism is very similar to the biological one, and yields ribonucleotides with the same anomeric carbon chirality as in biological systems. These results suggest that natural selection might have optimized – through enzymes – a pre-existing ribonucleotide formation mechanism, carrying it forward to modern life forms.

ChemInform Abstract: Catalytic Asymmetric Cyanation Reactions

ChemInform ◽  
2016 ◽  
Vol 47 (15) ◽  
pp. no-no
Author(s):  
Nobuhito Kurono ◽  
Takeshi Ohkuma
Keyword(s):  
Catalytic Asymmetric
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