Cited by 18Origins and Evolution of LifeChemical Synthesis and AnalysisAsymmetric Synthesis and Catalysis

Homochiral oligopeptides via surface recognition and enantiomeric cross impediment in the polymerization of racemic phenylalanine N‐carboxyanhydride crystals suspended in water

Nery, Jose Geraldo, Eliash, Ran, Bolbach, Gerard, Weissbuch, Isabelle, Lahav, Meir·2007·Chirality

Abstract

As part of our program on the search of possible prebiotic routes for the formation of oligopeptides of homochiral sequence (isotactic) from racemic precursors in aqueous environment, we report the polymerization of racemic crystals of phenylalanine N-carboxyanhydrides, enantioselectively tagged with five deuterium atoms, suspended in water containing various amine initiators. Racemic mixtures of isotactic oligopeptides, comprising up to 25 repeat units of the same handedness, as the dominant component for each length, were observed in a MALDI-TOF mass spectrometry analysis. The racemic mixtures of the peptides could be desymmetrized by initiating the polymerization reaction with water-soluble methyl esters of either enantiopure alpha-amino acids or dipeptides. A three-step mechanism is proposed to account for these results: (i) Surface recognition of the chiral initiator by the chiral sites present at specific faces of the crystal; (ii) Oligopeptide elongation at the polymer/crystal interface; and (iii) Self-assembly of the short isotactic peptides into racemic antiparallel beta-sheets as templates followed by cross-enantiomeric impediment in the growth of enantiomeric chains at the peptide beta-sheet/crystal interface.

Integrity signals

Registry

Crossref · 10.1002/chir.20363

Cites

42 of 42 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

We couldn’t retrieve this paper’s full text, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • The stereoselectivity of the oligomerization reaction is strongly enhanced under conditions for which β-sheet aggregates are initially present or emerge during the reaction process.

    “These authors found that the stereoselectivity of the oligomerization reaction is strongly enhanced under conditions for which b-sheet aggregates are initially present 549 or emerge during the reaction process.”
  • These supramolecular aggregates serve as templates in the propagation step of chain elongation leading to long peptides and copeptides with a significant bias towards homochirality.

    “These supramolecular aggregates serve as templates in the propagation step of chain elongation leading to long peptides and copeptides with a significant bias towards homochirality.”

Cites

Flagged first, then by citations

Cited by

Sorted by citations

Authors
Nery, J. G., Eliash, R., Bolbach, G., Weissbuch, I., & Lahav, M.
Affiliations
Weizmann Institute of Science (IL)
Corresponding author
Lahav, Meir
Venue
Chirality
Publisher
Wiley
Published
2007-03-12
Volume
19
Issue
8
Pages
612-624
ISSN
  • 0899-0042 (ISSN-L)
  • 1520-636X
OpenAlex
W2080759069
Cited by
18
References
42
Citations by year
2024: 1 · 2023: 1 · 2022: 1 · 2012: 3
FWCI
2.00
Type
journal article
Language
en
Open access
closed
Locations
  • Chirality (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
  • Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
Keywords
racemic crystals, surface recognition, deuterium labeling, peptide self-assembly, antiparallel beta-sheet, polymerization mechanism, aqueous polymerization
MeSH terms
Anhydrides, Crystallization, Microscopy, Electron, Scanning, Models, Molecular, Oligopeptides, Peptides, Phenylalanine, Solutions, Stereoisomerism, Water, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review