Neurotrophic peptide aldehydes: solid phase synthesis of fellutamide B and a simplified analog

Bioorg Med Chem Lett. 2006 Jul 15;16(14):3855-8. doi: 10.1016/j.bmcl.2006.04.029. Epub 2006 May 11.

Abstract

A combination of solid phase and solution phase synthetic methods have been used to complete the total synthesis of the neurotrophic lipopeptide aldehyde fellutamide B (2). The beta-hydroxy aliphatic tail was prepared by regioselective reductive opening of a cyclic sulfate, and later coupled to a solid phase resin. The synthetic compound was then examined in cytotoxicity and nerve growth factor (NGF) induction assays. A simplified analog of fellutamide B also showed activity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / pharmacology
  • Amino Acid Sequence
  • Animals
  • Cell Line
  • Cyclization
  • Dipeptides / chemical synthesis*
  • Dipeptides / pharmacology
  • Fibroblasts / pathology
  • Humans
  • Inhibitory Concentration 50
  • Lipopeptides
  • Mice
  • Molecular Sequence Data
  • Molecular Structure
  • Neoplasms, Glandular and Epithelial / pathology
  • Nerve Growth Factors / metabolism
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Pheochromocytoma / pathology
  • Rats
  • Sulfates / chemistry

Substances

  • Aldehydes
  • Dipeptides
  • Lipopeptides
  • Nerve Growth Factors
  • Oligopeptides
  • Sulfates
  • fellutamide B
  • fellutamide A