34980-66-0Relevant articles and documents
Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation
Fernández-García,Grefenstette,Powner
supporting information, p. 4919 - 4921 (2017/07/11)
RNA is essential to all life on Earth and is the leading candidate for the first biopolymer of life. Aminooxazolines have recently emerged as key prebiotic ribonucleotide precursors, and here we develop a novel strategy for aminooxazoline-5′-phosphate synthesis in water from prebiotic feedstocks. Oxidation of acrolein delivers glycidaldehyde (90%), which directs a regioselective phosphorylation in water and specifically affords 5′-phosphorylated nucleotide precursors in upto 36% yield. We also demonstrated a generational link between proteinogenic amino acids (Met, Glu, Gln) and nucleotide synthesis.
FURANOSE RING ANOMERIZATION: A KINETIC STUDY OF THE 5-DEOXYPENTOSES AND 5-O-METHYLPENTOSES
Snyder, Joseph R.,Serianni, Anthony S.
, p. 13 - 26 (2007/10/02)
The anomerzation of 5-deoxy-L-pentoses (1-4) and 5-O-methyl-D-pentoses (5-8) in aqueous solution has been studied by (13)C saturation-transfer n.m.r. (s.t.-n.m.r.) spectroscopy, using compounds substituted with (13)C at the anomeric carbon atom.Unidirectional rate-constants of ring-opening (kopen) and ring closing (kclose) have been obtained for these compounds under identical solution conditions (50mM acetate buffer, pH 4.0 at 60 deg C), and have been compared to those measured for the D-tetroses (9 and 10) and four D-pentose 5-phosphates (11-14).Based on these comparisons, several correlations between furanose structure and reactivity have been revealed, and models have been proposed to explain the observed kinetic behavior of compounds 1-10.The effect of exocyclic structure on acid-catalyzed rate-constants was also examined by comparing the behavior of 5-deoxy-L-lyxose and 5-O-methyl-D-lyxose.Some consideration has been given to identifying the factors (enthalpic and entropic) that may play roles in determining the effect of structure on anomerization reactivity.