Transfer of Stereochemical Information in a Minimal Self-Replicating System

VC Allen, Douglas Philp, N Spencer

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

[GRAPHICS]

The rational design, synthesis, and characterization of a minimal self-replicating system based on a 1,3-dipolar cycloaddition between a nitrone and a maleimide is presented. The importance of molecular recognition in this system is demonstrated using a competitive inhibitor. Doping experiments demonstrate that only one of the two diastereoisomeric products of the cycloaddition reaction is capable of acting as an efficient template for its own formation, accelerating the reaction between the nitrone and maleimide and controlling the stereochemical outcome of the reaction.

Original languageEnglish
Pages (from-to)777-780
Number of pages4
JournalOrganic Letters
Volume3
Publication statusPublished - 8 Mar 2001

Keywords

  • DIELS-ALDER REACTION
  • MOLECULAR RECOGNITION
  • AUTOCATALYSIS
  • CATALYSIS
  • HEXADEOXYNUCLEOTIDE
  • RECEPTOR

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