28047-05-4Relevant articles and documents
Mixed Anhydride Intermediates in the Reaction of 5(4H)-Oxazolones with Phosphate Esters and Nucleotides
Liu, Ziwei,Rigger, Lukas,Rossi, Jean-Christophe,Sutherland, John D.,Pascal, Robert
, p. 14940 - 14949 (2016)
5(4H)-Oxazolones can be formed through the activation of acylated α-amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic-phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the results of a study aimed at investigating the chemistry that can be built through this interaction. As a matter of fact, the formation of mixed anhydrides with mononucleotides and nucleic acid models is shown to take place at positions involving a mono-substituted phosphate group at the 3’- or 5’-terminus but not at the internal phosphodiester linkages. In addition to the formation of mixed anhydrides, the subsequent intramolecular acyl or phosphoryl transfers taking place at the 3’-terminus are considered to be particularly relevant to the common prebiotic chemistry of α-amino acids and nucleotides.
Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings
Beaufils, Damien,Danger, Gregoire,Boiteau, Laurent,Rossi, Jean-Christophe,Pascal, Robert
supporting information, p. 3100 - 3102 (2014/03/21)
A stereochemical study of a potentially prebiotic peptide-forming reaction was carried out as the first part of a systems chemistry investigation of potential paths for symmetry breaking. Substantial diastereomeric excesses result from a fast epimerization of the 5(4H)-oxazolone intermediate in aqueous solution. The Royal Society of Chemistry.
Synthesis and application of peripherally alkyl-functionalized dendritic pyrphos ligands: Homogeneous-supported catalysts for enantioselective hydrogenation
Yi, Bing,He, Hua-Ping,Fan, Qing-Hua
experimental part, p. 82 - 85 (2010/04/25)
A new series of dendritic ligands with a chiral diphosphine located at the focal point have been synthesized through coupling of (R,R)-3,4-bis(biphenylphosphino)pyrrolidine (pyrphos) with peripherally alkyl-functionalized benzoic acid dendrons. These ligands were employed in the Rh-catalyzed asymmetric hydrogenation of prochiral dehydroamino acids, exhibiting excellent catalytic activities and enantioselectivities. The second-generation dendritic catalyst could be recovered by simple liquid-liquid biphasic separation and reused four times without serious loss of its activity and selectivity.