Synthesis and biological evaluation of sperm CD52 GPI anchor and related derivatives as binding receptors of pore-forming CAMP factor

Carbohydr Res. 2008 Jul 21;343(10-11):1718-29. doi: 10.1016/j.carres.2008.03.033. Epub 2008 Apr 4.

Abstract

Sperm CD52 GPI anchor and its derivatives containing different carbohydrate chains were prepared in a highly convergent fashion starting from the same properly protected phospholipidated pseudodisaccharide. Coupling this common key intermediate to various oligosaccharyl donors quickly afforded the framework of the synthetic targets, which was followed by global deprotection to furnish the desired structures. Preliminary studies on the biological properties of the synthetic GPI derivatives indicated that both the intact GPI anchor and the free phospholipidated pseudodisaccharide interacted strongly with CAMP factor, a pore-forming bacterial toxin.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antigens, CD / metabolism*
  • Antigens, Neoplasm / metabolism*
  • Bacterial Proteins / metabolism*
  • CD52 Antigen
  • Glycoproteins / chemical synthesis*
  • Glycoproteins / metabolism*
  • Glycosylphosphatidylinositols / chemical synthesis*
  • Glycosylphosphatidylinositols / metabolism*
  • Hemolysin Proteins / metabolism*
  • Humans
  • Male
  • Spermatozoa / chemistry

Substances

  • Antigens, CD
  • Antigens, Neoplasm
  • Bacterial Proteins
  • CAMP protein, Streptococcus
  • CD52 Antigen
  • CD52 protein, human
  • Glycoproteins
  • Glycosylphosphatidylinositols
  • Hemolysin Proteins