Convergent approaches for the synthesis of the antitumoral peptide, Kahalalide F. Study of orthogonal protecting groups

J Org Chem. 2006 Sep 15;71(19):7196-204. doi: 10.1021/jo060976f.

Abstract

Kahalalide compounds are peptides that are isolated from a Hawaiian herbivorous marine species of mollusc, Elysia rufescens, and its diet, the green alga Bryopsis sp. Kahalalide F and its synthetic analogues are the most promising compounds of the Kahalalide family because they show antitumoral activity. Linear solid-phase syntheses of Kahalalide F have been reported. Here we describe several new improved synthetic routes based on convergent approaches with distinct orthogonal protection schemes for the preparation of Kahaladide analogues. These strategies allow a better control and characterization of the intermediates because more reactions are performed in solution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Depsipeptides / chemical synthesis*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification
  • Mollusca / metabolism
  • Protein Conformation

Substances

  • Antineoplastic Agents
  • Depsipeptides
  • kahalalide F