Download PDF
Synlett 2000; 2000(6): 0797-0800
DOI: 10.1055/s-2000-6722
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Facile Solid Phase Synthesis of YEE(ah-GalNAc)3, a Ligand with Known High Affinity for the Asialoglycoprotein Receptor

Weir-Torn Jiaang* , Ping-Hui Tseng, Shui-Tein Chen
  • *Institute of Biological Chemistry, Academia Sinica, Taipei, 115, Taiwan; E-mail: bcchen@gate.sinica.edu.tw
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

A simple cluster glycoside, containing three residues of N-acetylgalactosamine with proper inter-residual distances, can be a high-affinity ligand for the asialoglycoprotein receptor (ASGPr) of mammalian liver. Tris(GalNAc-aminohexyl)glycoside of tyrosyl(glutamyl)glutamate YEE(ah-GalNAc)3 1, which is known to have sub-nanomolar affinity for the asialoglycoprotein receptor, was efficiently synthesized by using succinic acid as a linker to anchor GalNAc-aminohexyl glycoside to solid phase resin, followed by coupling the building blocks of Fmoc-(ah-α-GalNAcAc3)Glu and Fmoc-Tyr-OH to obtain YEE(ah-GalNAc)3 with a total yield of 83%.

asialoglycoprotein receptor - ligand - cluster glycoside - solid phase - oxazoline