Efficient sequential segment coupling using N-alkylcysteine-assisted thioesterification for glycopeptide dendrimer synthesis

Org Lett. 2008 Aug 21;10(16):3531-3. doi: 10.1021/ol801340m. Epub 2008 Jul 19.

Abstract

A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted thioesterification. The glycopeptide having C-terminal NAC was prepared by the Fmoc method and converted to the thioester by 3-mercaptopropionic acid treatment. The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, which was then converted to the thioester. Two tetramers were condensed with ethylenediamine to give the octameric glycopeptide dendrimer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry*
  • Dendrimers / chemical synthesis*
  • Dendrimers / chemistry
  • Esters / chemistry*
  • Glycopeptides / chemical synthesis*
  • Glycopeptides / chemistry
  • Molecular Sequence Data
  • Sulfhydryl Compounds / chemistry*

Substances

  • Dendrimers
  • Esters
  • Glycopeptides
  • Sulfhydryl Compounds
  • Cysteine