Development of homochiral peptides in the chemical evolutionary process: Separation of homochiral and heterochiral oligopeptides

Living organisms have one‐handed structures of L‐amino acids in proteins and D‐sugars in nucleic acids. Although the origins of each one‐handed structure (or homochirality) have been discussed for many years, these discussions have been restricted to monomeric compounds, such as amino acids and mono...

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Published in:Chirality (New York, N.Y.) N.Y.), 2003, Vol.15 (S1), p.S108-S115
Main Authors: Munegumi, Toratane, Shimoyama, Akira
Format: Article
Language:English
Subjects:
Alanine - chemistry
calculation
Chromatography, High Pressure Liquid
homochirality
hydrophobicity
log P
Models, Chemical
Oligopeptides - chemistry
Peptides - chemistry
Stereoisomerism
Time Factors
water-solubility
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Summary:Living organisms have one‐handed structures of L‐amino acids in proteins and D‐sugars in nucleic acids. Although the origins of each one‐handed structure (or homochirality) have been discussed for many years, these discussions have been restricted to monomeric compounds, such as amino acids and monosaccharides, or their stereospecific condensation reactions. Oligomers of these compounds have to be considered in the accumulation processes of homochirality because of the differences in physical properties of the diastereomers. High‐performance liquid chromatography (HPLC) and the calculation of the partition coefficient values showed that the peptides having heterochiral sequences like L‐Ala‐D‐Ala or D‐Ala‐L‐Ala were more hydrophobic than the peptides having homochiral ones (L‐Ala‐L‐Ala and D‐Ala‐D‐Ala). Similar results were given from the calculation of most linear dipeptides and all cyclic ones composed of Gly, Ala, Val, or Asp. In addition, longer homo‐oligopeptides composed of Ala, Val, or Asp also gave similar results. This general tendency would be useful for the separation of diastereomeric oligopeptides in water. The results also suggest that the separation of the homochiral peptides from the heterochiral ones by their solubility in water could have progressed in a primitive hydrosphere. Chirality 15:S108–S115, 2003. © 2003 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.10256