On the emerging role of chemistry in the fashioning of biologics: synthesis of a bidomainal fucosyl GM1-based vaccine for the treatment of small cell lung cancer

J Org Chem. 2009 Aug 7;74(15):5157-62. doi: 10.1021/jo900918m.

Abstract

The synthesis of the novel small cell lung cancer (SCLC) fucosyl GM1-based vaccine construct, featuring insertion of the HLA-DR binding 15 amino acid sequence derived from Plasmodium falciparum, is described. The resultant glycopeptide has been synthesized in an efficient manner. Finally, successful conjugation of the glycopeptide to the keyhole limpet hemocyanin (KLH) carrier protein completed the preparation of the vaccine.

Publication types

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

MeSH terms

  • Cancer Vaccines / chemical synthesis*
  • Cancer Vaccines / chemistry
  • Cancer Vaccines / immunology*
  • Carcinoma, Small Cell / therapy*
  • G(M1) Ganglioside / analogs & derivatives*
  • G(M1) Ganglioside / chemical synthesis
  • G(M1) Ganglioside / chemistry
  • G(M1) Ganglioside / immunology
  • Humans
  • Lung Neoplasms / therapy*
  • Vaccines, Conjugate / chemistry
  • Vaccines, Conjugate / immunology*

Substances

  • Cancer Vaccines
  • Vaccines, Conjugate
  • G(M1) Ganglioside
  • fucosyl GM1 ganglioside