Phosphoryl group differentiating ?-amino acids from ?- and ?-amino acids in prebiotic peptide formation

2003 ◽  
Vol 94 (4) ◽  
pp. 232-241 ◽  
Author(s):  
Yang Jiang ◽  
Bo Tan ◽  
Zhong-Zhou Chen ◽  
Tong Liu ◽  
Ru-Gang Zhong ◽  
...  
Keyword(s):  
Amino Acids ◽  
Phosphoryl Group ◽  
Peptide Formation ◽  
Prebiotic Peptide Formation

On the possible role of montmorillonites in prebiotic peptide formation

1994 ◽  
Vol 125 (10) ◽  
pp. 1033-1039 ◽  
Author(s):  
J. Bujdak ◽  
H. Slosiarikova ◽  
N. Texler ◽  
M. Schwendinger ◽  
B. M. Rode
Keyword(s):  
Peptide Formation ◽  
Prebiotic Peptide Formation

Prebiotic peptide-formation in the solid state

1975 ◽  
Vol 6 (3) ◽  
pp. 165-184 ◽  
Author(s):  
H. Sawai ◽  
R. Lohrmann ◽  
L. E. Orgel
Keyword(s):  
Solid State ◽  
Peptide Formation ◽  
Prebiotic Peptide Formation

A COMPARISON OF THE STEREOISOMERIC PENTA-COORDINATED PHOSPHORUS INTERMEDIATES FORMED FROM 19 DIMETHOXYL N-PHOSPHORYL AMINO ACIDS BY DFT CALCULATIONS

2011 ◽  
Vol 10 (02) ◽  
pp. 217-229
Author(s):  
LIJIAO ZHAO ◽  
TINGTING LIU ◽  
RUGANG ZHONG
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Density Functional ◽  
Molecular Structures ◽  
Phosphoryl Group ◽  
Hydroxyl Groups ◽  
Functional Theory ◽  
Important Species ◽  
Ester Exchange ◽  
Two Sides

N-phosphoryl amino acids (PAAs) are important species in the origin of life that self-catalyze and self-assemble into polypeptides and polynucleotides under mild conditions. Both experimental and theoretical studies have shown that a penta-coordinated phosphorus intermolecular mixed carboxylic-phosphoric anhydride (IMCPA) is formed as the common intermediate in these reactions. In this work, the mechanism for the formation of stereoisomeric IMCPAs from PAAs is investigated using density functional theory (DFT) calculations at the B3LYP/6-311+G(d,p) theoretical level. The molecular structures of the cis- and the trans-IMCPAs, as well as the transition states of the two stereochemical reaction pathways, were characterized in detail. The results showed that the hydroxyl groups of PAAs were situated in favorable positions for attacking the phosphorus atom from two sides of the phosphoryl group, resulting in the formation of the cis-IMCPA and the trans-IMCPA, respectively. The trans-isomers were predicted to be more likely to undergo a further reaction involving an ester exchange on the phosphorus than the cis-isomers. By comparing the relative energies of the IMCPAs and the activation energies, the trans-IMCPAs were computed to be more stable than the cis-IMCPAs, but the energy barriers for the formation of the trans- and the cis-isomers were similar. This work is expected to shed light on the stereochemical effect involved in the chemical evolution of biomolecules.

scholarly journals From amino acid mixtures to peptides in liquid sulphur dioxide on early Earth

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Fabian Sauer ◽  
Maren Haas ◽  
Constanze Sydow ◽  
Alexander F. Siegle ◽  
Christoph A. Lauer ◽  
...  
Keyword(s):  
Amino Acids ◽  
Sulphur Dioxide ◽  
Room Temperature ◽  
Early Earth ◽  
Peptide Bonds ◽  
Initial Reactant ◽  
Peptide Formation ◽  
Liquid Sulphur ◽  
Catalytically Active ◽  
Amino Acid Mixtures

AbstractThe formation of peptide bonds is one of the most important biochemical reaction steps. Without the development of structurally and catalytically active polymers, there would be no life on our planet. However, the formation of large, complex oligomer systems is prevented by the high thermodynamic barrier of peptide condensation in aqueous solution. Liquid sulphur dioxide proves to be a superior alternative for copper-catalyzed peptide condensations. Compared to water, amino acids are activated in sulphur dioxide, leading to the incorporation of all 20 proteinogenic amino acids into proteins. Strikingly, even extremely low initial reactant concentrations of only 50 mM are sufficient for extensive peptide formation, yielding up to 2.9% of dialanine in 7 days. The reactions carried out at room temperature and the successful use of the Hadean mineral covellite (CuS) as a catalyst, suggest a volcanic environment for the formation of the peptide world on early Earth.

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