A practical total synthesis of globo-H for use in anticancer vaccines

J Org Chem. 2009 Nov 6;74(21):8452-5. doi: 10.1021/jo901682p.

Abstract

An improved synthesis of the hexasaccharide MBr1 antigen (globo-H) is reported. Enhanced efficiency in the synthesis was necessary for the scale-up production of globo-H, in order to advance globo-H-based anticancer vaccines to clinical trials. The key features of the improved synthesis include preactivation-based glycosylations and a revised iodosulfonimidation/rearrangement.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antigens, Tumor-Associated, Carbohydrate / chemistry*
  • Cancer Vaccines / chemistry*
  • Carbohydrate Sequence
  • Molecular Sequence Data

Substances

  • Antigens, Tumor-Associated, Carbohydrate
  • Cancer Vaccines
  • Globo-H