Site-Selective Reactions with Peptide-Based Catalysts

Top Curr Chem. 2016:372:157-201. doi: 10.1007/128_2015_653.

Abstract

The problem of catalyst-controlled site-selectivity can potentially require a catalyst to overcome energetic barriers larger than those associated with enantioselective reactions. This challenge is a signature of substrates that present reactive sites that are not of equivalent reactivity. Herein we present a narrative of our laboratory's efforts to overcome this challenge using peptide-based catalysts. We highlight the interplay between understanding the inherent reactivity preferences of a given target molecule and the development of catalysts that can overcome intrinsic preferences embedded within a substrate.

Keywords: Asymmetric synthesis; Catalysis; Natural products; Peptides; Site-selective reactions.

Publication types

  • Review

MeSH terms

  • Catalysis
  • Erythromycin / chemistry
  • Glycopeptides / chemistry
  • Macrolides / chemistry
  • Oxidation-Reduction
  • Peptides / chemistry*
  • Phosphorylation
  • Pyrones / chemistry

Substances

  • Glycopeptides
  • Macrolides
  • Peptides
  • Pyrones
  • apoptolidin A
  • Erythromycin