Phosphoryl Promotion and Differentiation Effect on Amino Acids and Prebiotic Synthesis of Protein

Nitrogenous Derivatives of Phosphorus and the Origins of Life: Plausible Prebiotic Phosphorylating Agents in Water

“… Derivatives of CAPA 44 , 46 and acyclic N -alkylated phosphoryl amino acids intermediates 47, 48 and hexa-coordinated P–N intermediate 49 observed during the formation of small peptide mediated by phosphate species as explained by Yu et al [ 49 ]. …”

“…The reactivity of dual electrophilic centers present in α-CAPAs as determined by isotopic analysis ( 18 O, 15 N) was highlighted in another publication by Zhao et al [ 47 ]. The corresponding penta-coordinated N -dialkyl amino acid cyclic phosphates (P5-CAPAs) 46 could react both at the carbonyl and phosphorus center depending on the nature of the substrate [ 47 , 49 , 50 ]. The pathway involving the attack of a nucleophilic amine at the activated carbonyl center has already been shown (Orgel and Rabinowitz [ 44 ]) to produce short peptides.…”

From the Prebiotic Synthesis of α-Amino Acids Towards a Primitive Translation Apparatus for the Synthesis of Peptides

“…The possibilities of N-(dialkylphosphoryl)amino acids for the prebiotic syntheses of peptides and polynucleotides have been studied in a series of papers [24,[116][117][118][119][120][121][122]. However, it must be emphasized that the phosphoryl group does not behave as an amino-activating group, the hydrolysis of which would be coupled to peptide bond formation.…”

Investigation of Reaction Mechanism of Amino Acids and Phosphorus Trichloride by 31 P NMR and ESI-MS/MS

“…[4][5][6][7][8] Moreover, it was discovered that N-phosphoryl-α-amino acids and N,O-bis(trimethylsilyl)-α-amino acids could self-activate to produce peptides, and the reaction underwent a five-member cyclic pentacoordinated phosphoriccarboxylic mixed anhydride intermediate. [9][10][11] Recent studies showed that α-amino acids could assemble into homopeptide libraries with the assistance of inorganic phosphorus reagents, [12][13][14] and the oligopeptide libraries constructed by this method could be transformed to conjugated and phosphoryl oligopeptide libraries. 15,16 Further studies of our group showed that α-amino acids could assemble into not only linear polypeptides but also cyclic dipeptide with the assistance of phosphorus trichloride.…”