A new route to fullerene substituted phenylalanine derivatives

Chem Commun (Camb). 2004 Dec 21:(24):2884-5. doi: 10.1039/b411118d. Epub 2004 Oct 25.

Abstract

A series of fullerene substituted phenylalanine derivatives have been prepared by the condensation of 1,2-(4'-oxocyclohexano)fullerene with ester or Boc protected (4-amino)phenylalanine, H(2)NC(6)H(4)CH(2)CH(COR(1))(NHCOR(2))(where R(1) = OMe, R(2) = Me; R(1) = OH, R(2) = Me, O(t)Bu). Conversion of the imine to the corresponding amine is achieved by di-acid catalyzed hydroboration. Reaction of the N-Ac amino ester with BBr(3) led to the formation of the parent amino acid, while the Boc-protected derivative readily undergoes coupling with NH(2)-Gly-OEt. The reduction of the imine is not accompanied by hydroboration of the fullerene cage.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fullerenes / chemistry*
  • Molecular Structure
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis
  • Phenylalanine / chemistry*
  • Spectrum Analysis

Substances

  • Fullerenes
  • Phenylalanine