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Molecular discrimination of n-protected amino acid esters by a self-assembled cylindrical capsule: Spectroscopic and computational studies

Academic Article
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Overview

authors

  • Hayashida, O.
  • Sebo, L.
  • Rebek Jr., Julius

publication date

  • November 2002

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A self-assembled, cylindrical capsule was used to bind N-alpha-protected amino acid esters. The reversible encapsulation was studied using NMR spectroscopy in deuterated mesitylene solution and by computer-aided molecular modeling. BOC-L-alanine alkyl esters and BOC-beta-alanine alkyl esters were tested as guests, and the relative binding affinities were established by direct competition experiments. A good correlation was found between the experimental and calculated relative binding affinities in these two series. Guests that were slightly longer than the internal dimensions of the cavity were accommodated by adopting compacted conformations.

subject areas

  • Alanine
  • Amino Acids
  • Combinatorial Chemistry Techniques
  • Computer Simulation
  • Computers, Molecular
  • Esters
  • Macromolecular Substances
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Protein Conformation
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo0201171

PubMed ID

  • 12444605
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Additional Document Info

start page

  • 8291

end page

  • 8298

volume

  • 67

issue

  • 24

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