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Clefts as receptor and enzyme analogues

Academic Article
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Overview

authors

  • Rebek Jr., Julius

publication date

  • 1991

journal

  • Ciba Foundation Symposia  Journal

abstract

  • Synthetic receptors for small biological targets have become a popular research topic in molecular recognition. This paper discusses the optimal functional group complements and the scaffolds that are ideal for such purposes. Specifically, remote steric barriers are used to control the conformation of (that is, to preorganize) hosts derived from acridine skeletons, triaryl benzenes and related systems. These structures separate entropic effects from enthalpic effects and show that entropy is an important contributor to high affinity. In a comparative study lactams are shown to be superior to imides in their capacity for self-association. Imides are shown to have higher affinity than lactams for adenine derivatives because of the presence of an unconventional hydrogen bond. Finally, preorganization in the context of chemical catalysis is demonstrated in two systems, one involving hemiacetal cleavage and a second involving a self-replicating system.

subject areas

  • Chemistry, Physical
  • Enzymes
  • Imides
  • Lactams
  • Molecular Conformation
  • Molecular Structure
  • Physicochemical Phenomena
  • Receptors, Drug
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Identity

International Standard Serial Number (ISSN)

  • 0300-5208

Digital Object Identifier (DOI)

  • 10.1002/9780470514085.ch7

PubMed ID

  • 1935429
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Additional Document Info

start page

  • 98

end page

  • 114

volume

  • 158

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