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Cited by 31Origins and Evolution of LifeEvolution and Genetic DynamicsAsymmetric Synthesis and Catalysis

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Spontaneous Onset of Homochirality in Oligopeptide Chains Generated in the Polymerization of N-Carboxyanhydride Amino Acids in Water

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Hitz, Thomas H., Luisi, Pier L.·2004·Origins of life and evolution of the biosphere
DOI 10.1023/b:orig.0000009831.85557.25
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Abstract

This article is concerned with the spontaneous onset of homochiral oligopeptide sequences. We will show that the polymerization of hydrophobic NCA (N-carboxyanhydride = cyclic anhydride)-amino acid racemates (i.e. tryptophane, leucine and isoleucine) in aqueous solution yields oligopeptides that are characterized by a high degree of homochiral sequences. Furthermore we will show that quartz enhances efficiently the mole fraction of oligopeptides with homochiral sequence by selectively adsorbing the more stereoregular oligopeptides from an aqueous solution of oligo-D,L-leucine. We find in particular that the mole fraction of the adsorbed homochiral 7mers is 17 times larger than the mole fraction calculated for a theoretical, random process. Experimentally the stereoisomer distribution for each oligomer length can be determined by the use of enantio-labeling and LC-MS (Liquid Chromatography-Mass Spectrometry). Furthermore, if we start the polymerization with an enantiomeric excess (e.e.) of 20% of L-leucine (L-amino acid: D-amino acid = 6:4, molar ratio) we observe a chiral amplification in the enantiomeric homochiral oligopeptides. We think that such processes are relevant to the chemical evolution of single handedness.

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Research works printed but not linked: 22

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Metadata

Authors
Hitz, T. H., & Luisi, P. L.
Affiliations
ETH Zurich (CH)
Corresponding author
Luisi, Pier L.
Venue
Origins of life and evolution of the biosphere
Publisher
Springer Science and Business Media LLC
Published
2004-02
Volume
34
Issue
1-2
Pages
93-110
ISSN
  • 0169-6149 (ISSN-L)
  • 1573-0875
DOI
10.1023/b:orig.0000009831.85557.25
OpenAlex
W1984595210
Cited by
31
References
4
Citations by year
2023: 1 · 2022: 2 · 2020: 2 · 2019: 1 · 2018: 3 · 2017: 1 · 2014: 3 · 2013: 1 · 2012: 1
FWCI
1.54
Type
journal article
Language
en
Open access
Licence
Locations
  • Origins of Life and Evolution of Biospheres (publishedVersion)
  • PubMed (publishedVersion)
  • reroDoc Digital Library (submittedVersion)
  • Iris (Roma Tre University) (submittedVersion)
  • Repository for Publications and Research Data (ETH Zurich) (submittedVersion, other-oa)
  • ETH Zürich Research Collection
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Evolution and Genetic Dynamics
  • Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
Keywords
homochirality, oligopeptides, N-carboxyanhydride ring-opening polymerization, aqueous polymerization, tacticity, chiral amplification, enantiomeric excess, origin of homochirality, tryptophan, leucine, isoleucine
MeSH terms
Amino Acids, Anhydrides, Biopolymers, Oligopeptides, Stereoisomerism

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